Trail Daddy Episode 26: Damian Lillard’s Value for the 2025-26 Season | Trail Daddy: A Trail…

Trail Daddy Episode 26: Damian Lillard’s Value for the 2025-26 Season | Trail Daddy: A Trail…

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[Music] [Applause] [Music] Hello everyone and welcome again to Trail Daddy, hopefully one of your favorite Portland Trailblazers podcasts. I am Dave Deckard, managing editor of blazersedge.com. I’ve been on vacation for a couple weeks as listeners of the podcast have known. went to the steamy, moisty Midwest, rode some roller coasters, had some fun with the family and stuff like that while I was gone. The Blazers didn’t do much. They only Oh, signed Damen Lillard. I am hardressed to think of a bigger move they could have made. I guess if you got LeBron James, Kevin Durant, or something like that, that would have been a splashier headline. But other than that, there’s literally no player that they could have possibly signed that made more news or bigger impact, at least, you know, popularly, than Lillard did. So, I guess I need to go on vacation more often, uh, because everything exploded while I was gone. I ended up writing almost every day that I was gone, but of course, didn’t do the podcast. I’m glad to be back here, and we’re going to talk about the Lillard signing a little bit, plus a couple other things. So, uh, first things first, the Blazers got Damen Lillard for a midlevel exception. That’s circumstantial. What you think of that depends on your point of view. Now, it is true that plenty of free agents have been signed this summer, but the free agent market has been muted. Only one team, the Brooklyn Brooklyn Nets, really had what you would call a significant amount of cap space heading into the summer. Significant being more than a mid-level exception. That has depressed the market with Brooklyn the only guys bidding. The agents of NBA players knew that this was a bad summer to hit the open market, especially if you’re a good player because there’s no money available. So, you saw a lot of early contract extensions. people tried to maneuver to avoid this free agency period when they could. Which means that other than one or two people who got really big contracts cuz they’re that good, most free reagents have been getting very very modest contracts, Damen Lillard, with a full mid-level exception for three years, a player option at the end and a no trade clause got the best nonstar deal possible, which makes you raise some eyebrows considering his age and his injury status. Of course, he uh had an Achilles tear. He’s not expected to play even much if at all for the first year. So the Blazers paid compared to other free agents a premium price to get Dame. But he is Damian Lillard and that name carries more cache than any other modern NBA player in Portland. You can only compare him to two others in franchise history. Bill Walton of course and Clyde Drexler. Neither one of those obviously is someone that you’d sign at this point. Bill has passed on. God rest his soul and thank you Mr. Walton. Clyde Drexler uh of course is long retired and just as significantly both of them left the team under acrimonious circumstances and the rift was healed more or less in Walton’s case. Although he didn’t have to have much contact with the Blazers really. Clyde still doesn’t, which means two out of three swings at this. You’ve had a franchise level superstar who eventually you fell out with, and the aftertaste in your mouth is not good. The Blazers have actually cured that problem now with Lillard by bringing him back into the fold. They’ve undone the hard feelings occasioned in 2003 or 23 rather when he demanded a trade and got it. But then they didn’t trade him Miami. They traded him to Milwaukee, which caused its own riffs, and he hasn’t done so well there. And there’s been personal issues and all kinds of stuff in his own life. Basically, it’s been kind of a sucky two years. And I don’t think anybody, not Damian Lillard, not the Trailblazers, were probably happy with how that relationship ended up. Now, you have a chance to redo it. The cost is your full mid-level exception. The the the cost is really dollars. They probably won’t go into the luxury tax or if they do it will be mildly. It probably won’t impact over the next 3 years anything that they’re going to do. Maybe in 2028 it’ll be interesting to see if they need to make any moves that they can’t otherwise. But frankly the Jeremy Grant extension that they signed in 2023 and trading for Jrew Holiday this summer have way more of an impact in 2028 than Damen Lillard’s salary will. So look, it’s probably a no harm, no foul thing. If you’re looking at what are they doing on the court or what are they doing visav other free agents, they probably could have spent that money more wisely. But if you look at what is this going to mean emotionally to the franchise and what are they going to do with the money otherwise if they don’t spend it this way. This really was kind of I don’t want to say an emotional purchase that kind of insults them and Dame but it is a reputation. It is a aura signing as much as it is an actual practical signing. They hope for a lot of things from Dame in terms of I’m sure PR mentorship and stuff. We’ll get to that in a minute. But basically the beginning and the end of the story, the major parts anyway is that he is Damen Freaking Lillard and he’s back in Portland and that’s enough to justify that signing in their mind. And it’s good for him because he gets to rehab of course in Portland where he has a home where his family still is and that’s what he wanted to do in the first place. So he’s good to go too. and he got really a handsome contract all things considered. It’s what $42 million almost. That’s a lot of extra money on top of what he was already getting from when he got bought out in Milwaukee. So, it’s good for everybody involved basically, except maybe whoever’s paying the paycheck in 3 years will have an extra tariff or tax on uh Lillard’s contract basically because at that point, maybe you don’t expect him to be the best player in the world. Who knows with this injury if he’ll even suit up, but look, they’ll be still paying his salary. That’s that’s a cost that they’re going to absorb. Also, uh, honestly, the opportunity cost. Could they have done something else with that money then, even if they wouldn’t do anything with it now? Now, they’ll be able to use another mid-level exception at some point. I mean, that’s that’s not denied to them, but do they want to go into the tax? How high do they want to go? Stuff like that? You may have to squeeze some things uh in or forego them in 3 years because of this. But that’s a 2028 problem, not a 2025 problem for now. They’re good with all of it. He’s good with all of it. The fans, most of them are good with all of it. Whether it’s wise or smart or not, almost doesn’t matter. It’s one of those things that everybody’s good with. Now, let’s take a look at the onc court aspect. Look, first of all, Dame’s not going to play the majority of year one, like we said, maybe all of year one. It depends on the team situation, his rehab situation. He could probably pull a John Cena and come back early. John Cena in the Royal Rumble in Madison Square Garden, of course, came in 30th when he was not expected to even show up for another three or four months at minimum, and made a big splash. It was wonderful. You could see Dame do that perhaps. Uh but it’s more likely probably that he will rest up and heal up and try to come back the season after. What’s it going to look like will depend a lot on his health. Now there are people who have had Achilles tears who have come back and played for a couple years. There are people who have had Achilles tears and came back and played poorly. And there are people who have never come back at all. And we don’t know whether Lillard will be in one category or the other. We will have to see. If he does come back, the first question is, does he have his old ability? Is he able to move laterally? Is he able to elevate? Can he get free? Because otherwise, it’s not so much whether he can still hit the three. He probably can, but can he get clear to hit the three will be the question. Also, defense has always been a question with Dame, even in his prime. It was not getting better in Milwaukee. It will not get better with this injury or the rehab from it. So, I think we know what kind of defender Dame is right now. I think the Blazers will have to compensate for that if and when he ever comes back to play a major role. However, he could come back as the 15 to 18 minute guy, the the support system off the bench, the plugandplay player in the back court who either scored or ran the offense for a little bit while everybody else was resting. and he’s kind of a supercharged version of that substitute in that the crowd will go crazy every time he comes in and every once in a while he might have a fantastic game. If the Blazers depend on him for that, I think fair enough. The the bigger picture probably is they don’t expect to contend for a championship in the next three years anyway probably. So whatever he brings again will be to the good. It’s less that this is a smart or fantastic signing and more that there’s very few things wrong with it. That the floor, even if he doesn’t play, is good publicity. If he does play at all, anything that he gives you is a bonus. I do not foresee Dame coming back and taking a starting role. I do not foresee Dame coming back and playing 36 or even 32 or even 30 minutes per game on average for a season. I don’t see him playing 82 games. He may or may not approach 20 points a game. He may or may not approach significant double figures. It would not be a surprise to see Dame average 12 points or 14 points or eight points and never touch 20 points a game again given his age and injury. Maybe he gives you more. There’s always that possibility. But again, whatever he brings on the court, that’s not really what this deal is about. I think there’s some critics out there saying he doesn’t fit with Portland’s age timeline, their new approach. All of that is correct. He’s not a defender. He is a a basically kind of an isolation player or at least a ball dominant player. There are a lot of things that don’t fit, but once again, go back to the same thing. Damen freaking Lillard, that’s who he is. That’s who he will always be. He solves the PR problems. He solves a a whole bunch of other stuff in the locker room. Maybe he might even have a voice. We’ll talk about that in a second. There are hundred reasons to do this signing besides that. Would I have done this signing in a basketball sense? No. If I thought the Blazers were going to do something in the next couple years, probably not. Given the circumstances, it’s just hard to argue with. And that’s the point. I don’t think this was the best move possible. I don’t think it’s a terrible move. It’s just something that is with a really shiny package on the outside that makes you glad it’s Blazers Christmas. Now, let’s delve into the elephant in the room with Dame and with Drew Holiday, no matter what their age, no matter what their onc court expectations, and people are hating on me because I say they should be muted until proven otherwise. The expectations for Drew and Dame are actually, I think, pretty low. Look, I think that’s fair to say. I don’t think it’s unreasonable to say. And I think, by the way, had either of those players signed with any other team. Blazers fans would be saying, “Okay, Jaru signed with somebody, he’s been his stats have been down. Boston didn’t want to keep him and spend all the money to keep him. They traded him for a guy with an expiring contract. that kind of shows his value. He’s been on and off if you watched him at all in Boston. He there are nights when he looks good. There are nights when he does not look like Drew Holiday. That’s not likely to reverse. Uh and so look, he expectations for Drew should be muted. Not as low as for Dame because Drew can actually take the floor, but he’s not going to be the all-star Drew Holiday that you remember from two, three, four seasons ago. um let alone in his you know absolute apex years. Um it’s it’s not going to happen. So you have this weird dichotomy of getting the name Drew Holiday, getting the experience of Drew Holiday, but without getting the impact of Drew Holiday. It’s the exact same thing with Damen Lillard, only dialed up because he’s not actually playing. expectations need to be tempered for these guys and let them exceed them rather than you saying, “Okay, here’s Dame in the rotation. Here’s Drew in the rotation and then Shaden Sharp is going to excel and Scoot Henderson is going to excel and everybody’s going to be happy and everybody’s going to have the right amount of minutes and everything’s going to click. That’s not likely to happen. Things aren’t even going to click for those veteran guards the way we’re used to, let alone for everybody in synergy all at once. If that does happen, let it be a pleasant surprise and write it all day long. But you can’t plan on that. And this is where I want to go with this. One of the big things that Blazer fans are expecting and that media people have cited repeatedly, and the players themselves have denied this, and Coach Bilips has denied it, and I think there’s reason for that. It’s mentorship that suddenly Drew and Dame are going to mentor Scoot Henderson and ease him into his transition into the point guard role. And Scoot is so lucky because he has one of the classic point guards of all time in Chanty Bilips as a coach, the franchise face and the the guy who was generational before him in Damen Lillard. And then a completely different kind of point guard, defensive oriented, and you know, a classic winner in Drew Holiday. And between all three of those, they’re all going to open up Scoot’s head, pour all the knowledge in, mentor him flawlessly, and all of a sudden, Scoot will come out as this Mighty Morphin Power Ranger cyborg thing that’s larger than he ever was and is an amalgam of all those playing styles and he will all of a sudden blossom into the player he’s supposed to be. Now, maybe that will happen. I don’t want to discount the possibility nor the value of mentorship. I’ve had mentors in my careers. You’ve had mentors in yours possibly. It’s absolutely an indispensable part of the process. We all build on the shoulders of the people who came before us. If it weren’t for Damen Lillard and his effort and wisdom, if it weren’t for Drew Holiday, you know, building up a reputation in this league and helping define what point guard means, Scoot Anderson wouldn’t have the same value and platform. There’s a reason, by the way, Scoot Anderson was drafted third as a point guard besides just his athleticism and what have you. It’s because and his individual talent is what I mean. Uh it’s because point guards have been seen as super valuable over the last decade and a half in part because of the work of guys like Lillard and Holiday and their gamechanging ability and the way that they have taken over the NBA. All of a sudden, you know, the Blazers see Scoot hanging out there and go, “That’s the guy.” And I want him more than Aman Thompson or anybody else. Scoot is our man because he’s a hyper athletic point guard who can score and that ticks all the boxes or most of them that we want in the modern NBA. That’s Dame. That’s Drew. I mean full kudos and credit to them for that kind of thing. Okay. And Scoot owes them already in that sense. However, mentorship is a tricky thing. Okay, there are a bunch of things that go into it. The first thing is it needs to be voluntary. I remember as a young pastor coming into, you know, the church I had gone through, you get a four-year seminary degree in in my denomination. It’s a master’s degree. I have one of those. You do a year of internship in that four years. You do what they call clinical pastoral education. You go to a hospital for a few months and basically you be a chaplain. That’s what you do day and night and stuff like that. So you learn how to do that. There there a bunch of things. You got your theological degree and elements and all that stuff, right? So you come in with all that stuff much like a young point guard coming into the NBA with your experience such as it is with your skill set, with your training, with your coaching, with your whatever, right? and you’re ready to go. And then there are a couple ways it goes. First of all, there are a lot of helpful people around you. Some are congregation members, some are fellow pastors, some are other people. Like you can get it from books or whatever depending on what you read or study. But somewhere around you need help making that transition from basically the shore of school and the rest of your life into the waters of being a pastor and into the deep pool of the church which sometimes turn into a hurricane filled ocean. Right? So you’ve got to have some guidance or you’re just going to drift around and waste a lot of time trying not to drown or or get swept away by the sea and the storm. That’s granted. But it’s up to you to find that. The best mentorship happens when you bond with someone. Uh when you get to choose that and maybe you say formally, I want you to be my mentor. Maybe you just go out for coffee once a week and you talk or you you have them in Bible studies or other pastors meetings and you talk back and forth and you learn and you grow and you absorb what they have from their experience, their mistakes, their good parts, their bad parts from talking to them. and all of a sudden you realize I’ve been mentored pretty well into this and now I have way more knowledge and facility and ability than I had. That’s when it works well. I’ve also had the other type of mentorship tried where it comes from above. You got to get a mentor. We think this person would be right. We’re going to hook you up with them. Now, they may be right, but they may also be wrong. And often from an institutional point of view, the people that people see as good mentors for you may not be a fit because they’re not your style or they’re not your theology. They’re certainly almost never in your generation. Uh they don’t often have your outlook. And some of them are trying to do or have done or have succeeded at done doing things that you’re not trying to do. They succeeded in a very specific way of doing this that really worked for them. But that’s not you. And you are not there to do what worked for them. You’re not with the people that they served with. Your church assumptions and the culture and whatever has moved along. So the institution says, “Here’s your guy that we think is a brilliant mentor here, take them.” And if you can move on from that or if you can have limited contact or whatever contact you wish, take it or leave it. It’s okay. But when that formal relationship is pre-established, the reality is a lot of times it doesn’t work. Also, and I’ve had these before, you get the folks who come in and say, “I really want to be your mentor or I’m going to be your mentor.” Some of them, for instance, were pastors in the churches I served that are now in the congregation. Uh we don’t really allow pastors, it’s not supposed to happen, that a pastor who just served there then joins the congregation. That’s a huge conflict of interest and boundaries being broken everywhere. Hard for the new guy to come in. At least we prevent that. But a number of pastors kind of hang on afterwards and you’ll go to a different church and then they kind of act in a quasi neither fish nor foul role where they’re no longer the pastor of this church, but somehow they know a lot about pastoring and exactly what should be done. And somehow it’s almost always the things that they used to do. And they carry all the inherent assumptions of the job they used to do right into your church and right into your job. So if you want to change something, there’s inertia there and there’s a wall there and they’re almost working against you. And also they’re kind of almost competing with you in that other congregation members know that this used to be a pastor and they have a long career behind them. They were probably somewhat successful at least the way they’re selling it. And so when you say something as a young pastor that’s controversial or brings about change or brings what we call a prophetic word that something is not going right to the congregation, it’s easy for the congregation to then sidestep and go to that experienced pastor in the congregation say, “What do you think of this? Is this true? Is this not true? What did you do? What do you think we should do?” And all of a sudden, your position as the actual acting pastor ends up being being eroded by people who either want to mentor the congregation or want to mentor you in their way non-consensually. You didn’t choose this. They just happen to be in your orbit. Now, again, I’m not saying that we don’t need mentors. I had them. Hopefully, you have them. They’re important. But you see in the descriptions the institutional mentorship and or the uh personal mentorship vition from someone who’s not you who comes and says to you in essence I’m going to be your mentor and I’m going to make sure everybody else around you knows that I’m the expert here and not just you. You can see how those are problematic. Now look at Scoot Henderson’s situation. First of all, Scoot Anderson was drafted third overall in the 2023 NBA and B8 draft. Victor Webmanyama was the only person in that draft with a higher reputation and expectations than Scoot had. He was the number two player in that draft behind a number one generational superstar. He was meant to excel. He was expected to take this league by storm. He was not drafted there by accident. He had a rocket lit under him and was expected to ride it and to explode like a firework. That has not happened. But that doesn’t mean that Scoot Henderson is not Scoot Henderson. Those expectations are still with him. His personal talents and skills and athleticism that brought those expectations are still with him. This will be his third year in this league. He is expected over the next two years to make a major major leap forward to justify that draft pick and those expectations that came along with it. Okay, this is not his first year. This is not necessarily a comfortable situation for mentorship, even though he still needs it, can benefit from it, especially given the struggles in his first two years. He is just beginning to ascend into his own. He started it at really mid about third of the way through the season last year and he continued to get more or less stronger. Still not there yet, but he made enough strides to where you forgot his rookie season, which was pretty much a disaster. He’s meant to have open air in front of him in order to grow. He’s meant to have that position of point guard available to him with all the touches and the shots and the captaincy of the offense and all the things that go along with it. I’m not saying he’s automatically ready to inherit it right now, but there’s meant to be a path that’s very clear and very open for where he is literally right now this summer to that starting point guard position and his place of primacy on this team. Now all of a sudden in the same few weeks, first of all, Scoot Henderson gets defined as someone in need of a mentor, which even though practically accurate, also means by implication, you’re not there yet. And we’re defining you by you not being there yet. We’re not defining you by the open space in front of you. We’re not defining you even anymore by your potential to grow into that space and to take over this league. We’re defining you by the fact that you haven’t made it yet and we feel you need help making it because you’re not adequate on your own. I’m not saying that’s all this means. I’m not saying it’s completely an insult, but those overtones are there and they’ve been strong and they changed over the last month radically. When Scoot Anderson got done with his season in May, there’s reasonable expectation where he could go, you know what, I’m looking at this roster and unless they draft a point guard, I this position is ready for me next year and by gum, I think I’m ready for it and I’m going to do everything I can to fill it. this is my time in the space of a couple weeks now all of a sudden again redefined you’re not ready you need a mentor and bygum we’re going to get you a mentor institutional mentorship okay Scoot didn’t choose these trades didn’t choose to gum up the point guard position his team did that’s not in his control shows a little bit of a lack of definition of him as already inheriting this shield Alexer er at this point doesn’t have a mentor, right? Kobe Bryant, I mean, didn’t need a mentor in season 3. Now, they may have had them informally, but you did not see this kind of thing happening. Nobody said, “We’re going to bring in a mentor for Kobe Bryant or we’re going to bring in a mentor for Shay Gildas Alexander and we’re going to put them directly in his line of sight at his position.” May have said we’re going to bring in veterans or something like that to help this roster grow. Sure, not the same thing as what happened here. So, Scoot’s defined by having not made it yet in need of mentorship. Both quote unquote mentors are right in his sighteline at the point guard position. One of them is one of the most successful point guards of this generation, Drew Holiday, who has won a couple of championships and is known as the poster child for the archetypal point guard, which by the way, Scoot Henderson is not. He’s he’s not completely alien to to Jerus, but what Scoot was brought in for, he’s closer to like a Derek Rose than he is a Drew Holiday. So, you get a little bit of a stylistic mis mismatch, but a huge reputation for Drew. Okay. Well, I got this guy. Now, I got to negotiate this position with him, right? Then they sign Damen Lillard. Now, again, Dave’s not going to play, so you don’t have the same roadblock right in front. But Damen Lillard is not only a completely different kind of point guard than Scoot Henderson is. Damen Lillard is literally the last guy the Blazers were married to. Not just at this position, but with the whole franchise. This is like seeing the guy you’re dating bringing your ex back and bringing his ex back rather. And this is okay. This is not insignificant. Now, I’m not saying that Scoot has any personal animosity that he and Dame might be best friends. Scoot might be looking forward to Dame being there. not making any assumptions about what going what’s going on in Scoot’s head. All I’m saying is if you look at this situation organizationally and institutionally now here are two older guys with massive reputations in the league and in this case one of them with a massive in and aura and and and footprint on the very franchise you are trying to run. This is like the last guy that pastored your church coming back in and starting to sit in the congregation. There’s going to have to be some negotiation there. This is not a neutral situation. And again, this is the institution andor these personal people deciding about this mentoring relationship, not Scoot. Now all of a sudden, look at the blanket that is over Scoot Henderson’s head. Or the way I’ve put it a couple times, look at the ladder in front of him. Before it was clear it was just him based on his ability to climb that ladder from point A to point B. If he could climb it fast, he could get right up there no problem. Now he’s got two guys on the ladder with him reputationally and experience-wise above him. history with the league and the franchise above him and at the very least somewhere alongside of him because he hasn’t developed his own space, his own reputation, whatever it is yet, that ladder, that path is no longer clear. And in order to get from point A to point B, now he’s going to have to negotiate his way through and or past and or away from these two veterans. That is at least somewhat in conflict with the idea of mentorship itself in that those people are generally considered to be below you organizationally somehow in support of you. Uh they’re they’re you can walk on their hands. You can walk they will hold you up. Not you’re all three kind of aiming at the same thing. And here’s the other thing. Drew Holiday and Damen Lillard, I guarantee you, given their history and accomplishments, are not planning to go quietly into the night. Now, I’m not saying they automatically see themselves in competition with Scoot for the starting point guard job forever and ever. Amen. But they’re not going to give it to him. They’re not going to get out of the way. They’re not going to go, I’m a veteran now. I’m aging out. My role has to be small. I’m going to end up coaching as much as I am playing or whatever. Chanty Bilip said that wasn’t true. Drew Holidayiday said that wasn’t true. In essence, Damen Lillard kind of said that wasn’t true as well, though not in so many words. They are going to want to play. And this is the one of the differences between this and a classic organizational mentorship is that in an organizational mentorship usually there’s not a finite number of minutes for which everybody is competing. If your mentor works 8 hours and you work 8 hours those 8 hours don’t come into conflict. If your mentor worked four hours and it took four hours away from your job and your ability to work, that would be a much different mentorship. That’s the way the NBA is working. These guys are on a team, but they are individual players with individual careers. And you know what? The minutes that Damen Lillard plays at point guard will be minutes Scoot Henderson does not. The same with Jaru Holiday. So Dame and Jaru are going to be competing with each other for those minutes. And they are in effect competing with Scoot Henderson for minutes too. And they have an interest personal and otherwise in not giving up those minutes entirely nor their place of primacy and role on the team. So now you have a mentorship/competition scenario and that is neither classic nor easily resolved either. Long story short for all this spiel and I’m explaining this carefully for a reason and it is this. It is possible that this all works out great. Like I said at the beginning, Scoot absorbs all these things willingly and perfectly that Damen Lillard and Drew Holidayiday’s experience is transferable to Scoot and his style of play and his culture and his age that uh everybody’s willing and everybody works out the minutes and there’s no real, you know, competition in terms of struggle for those. It’s possible that works out. But I’m telling you, even if you lean on mentorship as one of the primary reasons to get Damon Drew on this team, this is not a simple nor problemfree relationship. And if they don’t know it now, they’re going to find it out. And it’s also possible that setting this up blunts Scoot Henderson as much as it helps Scoot Henderson or even more because now every growing pain that Henderson goes through passes through the filter of not just Coach Bilips, which you’d expect, but also Damen Lillard, the mentor, the experienced whatever. Drew Holiday, same thing. Should one of them be playing instead? How many pieces of advice do you get about this, that, or the other? Uh, can you make a mistake without three people all trying to grandfather you out of it or whatever it is that they’re doing? Can you make a mistake without losing minutes? Can coach Phillips play Scoot Henderson freely without getting into the temptation of Drew would be better or eventually Dame would be better or I can’t keep Dame on the bench because Dame is a bigger player than Scoot or whatever it is, right? Scoot’s now looking over his shoulder everything he does. Scoot is now passing through at least three filters everything he does. Scoot may now begin second-guessing himself everything he does. Why? Why do you think I need a mentor? Wasn’t I ready? I thought I was ready. My whole job is to be ready. I come out to be ready and I get all this advice as if I’m not ready. I can’t earn playing time freely as if I’m ready. You’re not going to give the ball to me cuz you got these other guys that you brought in instead of me because you thought I wasn’t ready. How am I ever supposed to excel to where I’m supposed to get with all of this interference? And by the way, it wears on me. And by the way, I if you don’t think I’m ready to inherit this job, how am I supposed to think I’m ready to inherit this job? It doesn’t take very long before that becomes emotionally muddled and confidence draining. And I’m telling you, there is a possibility that we go out the other side of this whole thing in another couple years or however long it takes. And we say, well, you know what? Scoot never made it in Portland. At first, he couldn’t step up. And just when he looked like he was ready to step up, there was so much interference, so many players around him, so many pieces of advice, so much competition for minutes, so much all this other stuff that the Dame Jaru stuff overshadowed Scoot. And now we don’t know who he is. All we know is he never ended up resting that position away from everybody else and making it his own. So, the Scoot Henderson era in Portland is over and he’ll need to try somewhere else where hopefully they’ll give him a fresh start. Hopefully, he hasn’t picked up too many bad habits or too much looking over his shoulder of every dang thing he does and he’ll be able to actually become the player he was supposed to be. The tricky thing is we won’t know if that’s because of Scoot or because of the environment he was put into. It’ll probably be a little of both. But my whole point in this is simply saying this mentorship thing may not be a completely problemf free or completely good thing for Scoot. And that possibility lies open and we’re going to have to see. So, the Blazers are certainly in for more interesting times than they had before we started this summer, but that does not mean necessarily that the Blazers are in for better times. If you ask me whether I’m more worried or less worried right now than I was at the beginning of the summer, I will say probably it’s somewhat of a wash. I felt that the team was incomplete and maybe still a little mismatched before summer started. I felt like they were going to need some moves and I definitely felt like 100% extending Anthony Simons and extending DeAndre Aton would have been huge mistakes because going onward with this team as it was was not tenable. However, there are and were possibilities. Scoot looked like he was improving. Shaden Sharp has basically another year to show who he is and we saw some glimpses anyway. Denny Obdia obviously great and Tammani Kamar obviously great. Donovan Klingan okay let’s see I would have said who they get in the draft and make sure that they don’t stick to the same old same old too much. Now the Blazers have alleviated some of that. They did not resign Simons and Eaton. In fact, they bought out Eightton and they traded Simons. So, that at least positive check mark. Have they got some new players in who provide some new wrinkles? I think Drew Holiday and eventually Damen Lillard do qualify. So, that’s good. However, those fears have been replaced by some others. First of all, you know, both are 30. Dame is really injured. Drew has been battling through some injuries at least. It looks like this looks like another Jeremy Grant situation and a Jeremy Grant situation was not look working out for Portland really well last I checked. So that is a worry. Are these guys even serviceable? If they are serviceable at what are they serviceable? And if they’re not serviceable on the court what is the offc court impact and is that automatically good? And I think there’s not a clearer answer to any of those questions than there was to the questions the Blazers started the summer with. To me, Portland has just changed and exchanged one set of questions for a different set of questions without really necessarily answering any of those questions. That doesn’t put them in a better position. It just leads to new avenues of inquiry and probably eventually just different cracks for opponents to exploit. Now the advantage is at least we know these questions haven’t been answered yet. We know with last year’s team and the team the year before that I think that avenue of approach those questions have been answered and the answer is no. But here’s the thing. These questions not only need to be answered, they need to be answered definitively enough to where the Blazers go significantly higher. And by significantly, significantly, I mean, not just battling for a playin position, not just even battling for a lower bracket spot in the guaranteed first round. Those are nice things. They would be a step forward, but they’re a poor ceiling for Portland. And you know what? That’s not that’s not worth all this contract money that you’re paying to these veterans. Jeremy Grant, Drew Holiday, Damen Lillard. We’re talking $80 million a year for three players. That’s a lot of money to battle for the play in. That’s not where the Blazers are supposed to be going. It’s not an sufficient step forward, even if it might be an adequate one for this year. I don’t think their questions even definitively answer whether they can make the playoffs still in the West, let alone answer things well enough to where you go, now this is the the moment when they made the leap ahead where we start to see the ascension into them becoming a valid and perpetual if not a dominant playoff team. Too many questions, too many issues, too many mismatches still, and too much muddying of the waters until they actually answer some questions, which they may do on the floor, but I don’t know. Until they do, I don’t see a lot of progress here. And that always worries me when you make a lot of big moves but you have not definitively made a lot of big progress. When the Blazers got Maurice Lucas from the ABA expansion draft, I think a lot of people at the time, a little before my time, but from what I read historically, a lot of people went that’s going to be progressed. They could be scary. Bill Walton and Maurice Lucas themselves knew they went out to dinner. If you read, it was Halberst’s book or something like that, but you read that they went out to dinner and they looked at each other and said, “We can contend for a title and that’s what we’re going to do.” When Buck Williams came to this team, he and Clyde Drexler looked at each other and said, “We have championship material here, and we know it. We have just made a step forward that is going to make the league reckon with us and deal with us.” The Blazers have made some semi big splashy moves this summer, but they haven’t made any sort of move that would even barely cause them to rise in their own consciousness, let alone the league’s consciousness as having made that kind of step forward or even a guaranteed significant step forward. Is anybody anybody anywhere forecasting after these moves that the Blazers are even going to get homecourt advantage for one round of the playoffs? I’m not talking about contending with Oklahoma City in the first seed or Minnesota even or even Denver where they are. I’m not talking about that. I’m not talking about battling for a top seed. Is anybody thinking the Blazers will even battle for the fourth seed? The freaking fourth seed in the West. I haven’t heard it and I don’t see it. Is anyone forecasting the Blazers at six? I think that would be the tippity top super optimists would go, hey, maybe they can grab a guaranteed seed. They might make it around six. And by the way, that’s a big bundle of people in the West. That’s not a real definitive mark. There are a lot of people who could be six seed in the West. I don’t think most people are forecasting the Blazers there either. I mean, we’re talking about eighth, ninth, 10th. And you know what? From a real optimistic point of view, you could have gotten there from that perspective last year. In fact, they almost did with 36 wins. Had things gone a little different for Phoenix and, you know, a couple of teams ahead of them, they might have been in that playin position. Okay, you make these big moves, at least splashy moves, let’s call them that, and you haven’t made progress. I wonder about that. Now, the great hope is as we close here, and I spent a lot longer on this than I thought I was going to, but I think philosophically this is an important thing to go over, I think that there is still the chance that was always there, and that simply is. Scoot Anderson climbs that ladder from point A to point B, or Shaden Sharp does, or Denny Odia and Tammani Kamar continue to click and bring someone else along with them. So, there’s three now. Maybe Donovan Klingan becomes a defensive monster in his second year now that he understands conditioning and positioning and all that. I mean, Young Hansen, I think, is going to take longer than people think probably, but he’s going to show sparks right away. And, you know, I maybe it is him. I doubt it this year, but if the point is if there’s hope of real progress, it still lies with those people. It does not lie, I think, with Damen Lillard. It does not lie with Drew Holiday. Probably doesn’t even lie at this point with Jeremy Grant. Although I still think and I this confuses me why people assume that Drew Holiday is going to bounce back and have a great year on a fractured team where he’s might not be playing the minutes he’s used to playing and certainly won’t be playing the role he’s used to playing. Why people think he’s going to bounce back and be fantastic. Whereas Jeremy Grant, who got screwed around last year, but has a chance at least to win a significant role on this team. And Jeremy’s only 31, Jeru’s 35, Dame’s 35. Why people think Grant can’t bounce back after one down year and Jeru’s automatically going to do it after two? That mystifies me. And I don’t, you know, it’s I think people’s like glasses are a skew somewhat. They got one contact in and everything’s fuzzy. However, I think that ultimately the answer doesn’t lie with any of those veterans that we just named. It still lies with the young folks. So, let’s hope that that pans out. One advantage, by the way, one more detail. Be aware that the Blazers may be angling for making the playoffs. getting out of the lottery would be good in terms of giving up that pick to Chicago. Now, it’s a long way to go to get there, but it’s kind of an ancillary benefit. I doubt they would make all these moves just to get rid of that pick. They could probably negotiate or the pick obligation. I mean, they could probably negotiate that with Chicago to take a pick and then their swaps in 2028, whatever would be free and clear. But just in case as 2028 approaches and the Blazers want to make sure that they’re in position to benefit if Milwaukee stinks and Portland wants to have its own pick to swap with them, etc., etc. Okay, getting rid of that obligation to Chicago from the Larry Nance Jr. trade would be good. If the Blazers made the playoffs this year, that would do it. Now, it’s a strong draft this year. If the Blazers make the lottery, I think they sure wouldn’t want to give it up. But, you know, maybe that’s an ancillary benefit and something you could look forward to. Something that on the side, like a side dish would be, okay, we got Drew, we got Dame. If he comes back for the playoffs, we actually made the playoffs and now that pick is finally transferred, and now it’s free and clear between here and 2030. So be it. That could be good. But other than that, I think that I don’t know. you’re going to have to convince me that this made a real difference and wasn’t just looking really good at being kind of bad. And let’s hope that, you know, things do improve. And let’s hope that that improvement is significant enough that when we’re not talking about 38 or 40 wins as the beall and endall of everything next year, let’s hope that, you know, really if they make a leap, they get 44 or 45, they get way into the playoffs and continue growing. We’ll see if that happens. Anyway, I’m going to let you go for now. I’ve gone on long on this. We will be back in a couple weeks to talk more about the Blazers. I doubt there will be any moves between now and then, but we can delve more into the onc court permutations, other young players we haven’t talked about, and of course, any news that comes along between now and then. Until then, it’s been good to be with you, and if you can leave a like or a review that’s positive or something like that, or tell a friend about the podcast, uh, you know, look, we’re not living and dying with this. It’s kind of a fun project, but it’s always nice to get good feedback and, you know, get people listening. So, help us out if you can. Until then, we hope that your August is going really well, and let’s see what the next couple weeks bring. [Music]

What is the value of Damian Lillard to the Blazers in 2025? On court play? Mentorship? And, by the way, what are the ins and outs of mentorship itself? The NBA holds parallels, but also significant differences from your ordinary mentorship situation. All this and more this week on Trail Daddy!

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