Celtics Trading Jrue Holiday to the Trail Blazers for Anfernee Simons & Draft Picks

Celtics Trading Jrue Holiday to the Trail Blazers for Anfernee Simons & Draft Picks

uh damn we have a trade Uh overnight breaking overnight My phone was blowing up because as a New Englander who does work for the Blazers uh this was right in my wheelhouse Um lot of people were very confused about this trade Drew Holiday is being traded from the Boston Celtics to the Portland Trailblazers for Anthony Simons and two future second round picks The 2030 Knicks second rounder and the Blazers own 2031 second rounder going to Boston into the deal Um it took me a while to kind of wrap my head around this one Dan to be honest because uh it didn’t seem like any rumblings of a reunion with Drew Holiday after the the the Blazes acquired Drew Holiday in the Damon Lillard trade and then flipped him again um to Boston and then for for Malcolm Brogden and then they flipped Malcolm Brogden
and a first a couple first over for Denny Odia So this is full circle in many ways for the Blazers to reacquire Uncle Drew And I think that’s the way I’m thinking about it from the Blazers side is Uncle Drew is like
Drew Holiday is this amazing beloved teammate
for Scoot Henderson and Shaden Sharp at backcourt was really struggling to defend at a high level in the second half of next of of last season when Chanty Bils made the switch January 19th to move Shaden Sharp out of the starting lineup Some of that was because he needed better defense in the back court It’s one thing to have one guy and who’s who’s not a plus defender in the back court in Anthony Simons but it’s tough to have two of those And so now they get Drew Holiday who’s one of the best if not the best perimeter defender over the last few years Um and he is coming in at 35 years old He just celebrated his 35th birthday But like we’ve seen this before with young teams that are trying to make it with a young uh team that you get a guy who’s a floor general like Drew Holiday You look at Fred Van Vleet with the Houston Rockets and you look with Pat Bev with the Minnesota Tiberbrals a few years back and even if you want to go back even further in 2020 with Chris Paul and Shay Gildress Alexander with OKC there is reason to believe that the the there are much better things coming forward for Portland not just Encore stuff but also veteran leadership and Drew Holidayiday
Yeah So so to me I think the thing that jumped off the page right away was like wait a second the Blazers gave up two second round picks and the younger guy to get Drew Holidayiday who has like $104 million still coming to him over the next few years So I think like that’s the part that I think a lot of people are kind of stuck on like why the Blazers were 10 games under 500 last year They were not even like in the playin mix Why would they make that kind of move and I think that the way to think about it is like the Blazers are at a point where they I mean they haven’t been good in five years right like they have not been a they haven’t snipped 500 since 2021 Haven’t won a playoff series in I think six or seven years at this point and they’re coming to decision points on some of their younger guys right like you mentioned Shaden Sharp I believe extension eligible this summer Um or if not this summer the next Scoot Henderson same like extension eligible next summer And those guys are are both younger than uh Anthony Simons and they they are still under team control for longer with decisions coming Anthony Simons entering the last season of his extension this year And what we know is like all right he’s not a there’s a lot of really good things about Anthony Anthony Simons and I want to get back to that in terms of him in Boston in a second but like he’s not quite a point guard like a lead on ball creator right for a full-time for your full-time offense to be a good offense He has been by a variety of metrics including estimated plus minus or Taylor’s metric uh at dunks and threes one of the worst defenders in the league several years like a consistent negative net negative there for a team that is now like looking to build through its defense This felt like an opportunity to say like we we create some runway for two guys we need more information about to make decisions like next summer the next year to see what they can be And we move one of our more damaging players off to the side to see if what we were last season where we were like a top five defense for the last half of the season if that can be real enough to be competitive and like take a shot at being good Maybe like this is a just I’m I’m getting old but I’m like shouts out to trying to take a shot at being good Like yeah I understand the general idea of like this does not necessarily get the Blazers to a championship right but like if you haven’t been good in a while and you just extended your coach you just extended your your you know lead executive and Joe Cronin you are a franchise that is for sale and there’s like you know like but you there’s something maybe to be excited about like try to lean into that and see how good you can get I think there’s something to be said for that And I think Drew Holiday as that mentor figure you know other other examples like Mike Connley in Minnesota too right like and or you know Chris Paul in San Antonio like that obviously has not turned into a playoff team yet but like developing the growth for those young guys showing them how to be that floor general be the leader on the floor get you organized and also what it takes to defend at a high level night after night at the back court positions you maybe you remove the weakest link you provide a developmental roadmap for some of these young guys Like I don’t hate it I’ll tell you one thing Dan No one’s going to want to go full court against Tom Kamar and Drew Holiday Like they are going to be so hard to dribble up the floor like they were already the Blazers were already just one of the best in 24 second violations uh forced and 8second violations forced last year They were leading the league often times with picking up full court with Tammani Kamara and Scoot Henderson And now you got Drew Holiday one of the best at doing this andounding ball handlers It’s going to be hell going against the Blazers defense this upcoming season right and this is kind of the prototype What were we talking about all final all throughout the playoffs in the finals right like the the the idea of an advancing style of play that the Indiana Pacers were showing you that with Lou Dort picking up in the picking up full court that the Thunder were showing you Like I’m not saying that the Blazers are going to vault right into that but like this is this is a move you make to say like our identity is going to be stress you out 48 minutes 94 feet right and like
yes
with you know Donovan Klingan you know heading into year two as as a rim protector behind it with Denny Odia Jeremy Grant like big wings big forwards who can switch and defend across multiple positions Matis Thyel who you know has injuries and has difficulty staying on the court but like is a really you know can be an impactful perimeter defender switchable across positions picking up full court like you’re seeing a style develop here and I think there’s worse ways to build out your roster in 2025 Yeah And I I will say this it’s gonna be in in 2728 Drew Holiday has a player option for $37 million when he’s going to be uh 37 years old I expect him to pick that up But also that uh that will be a trade chip Like if the if the Blazers decide in a couple years they want to swing big for a player you’re going to need a contract that will fit that slot in order to match salary So there is value in taking a guy who’s a great locker room guy maybe the best locker room guy in the NBA like universally if you get that guy and to to to basically tutor Scoot Henderson who’s still super young you know came into the NBA as a teenager and same thing with Shaden Sharp Like Shaden Sharp is super young as well to have Drew Holidayiday be basically your mentor Um and then yeah in a couple years at 37 years old might not be the same player that he is right now but he’s still a good player And I think he fits exactly what Chanty Bilips loves to do is play extremely hard defense 94 feet exactly what the Indiana Pacers and the Oklahoma City we just saw do in the NBA finals The Blazers were doing that The Blazers were picking up full court with Tammani Kamar and now you get Drew Holidayiday They were a top five defense in the second half of the year And one thing that I always remember about Joe Cronin a year ago was talking about this past season looking ahead for this past season he wanted to get data He wanted to see what Anthony Simons Scoot Henderson Shaden Sharp what they were together because there just were so many injuries the year before They just didn’t know what they had in those young in that young back court What they had last season with Shaden Sharp and Anthony Simons their backcourt of the future so to speak was 21st percentile on defense when they were on the floor giving up 119 points every 100 possessions according to cleaningtheglass.com But more interesting to me their offense was 17th percentile as well So if you’re going to take away defensively and if you’re going to sacrifice your defense you better make it up on the other end of the floor and it just didn’t click with Anthony Simons and Shaden Sharp as much as you would have hoped for And so I think that was probably a little bit of a motivator too in this deal is like look if we’re not getting that elite offense with Anthony Simons and that synergy with Shaden Sharp maybe we try to get Drew Holiday to kind of double down on the defensive end where it’s just really hard in today’s NBA your weak link theory from uh from Owen Phillips at F5 It’s going to be really tough to have two of those guys on the floor at the same time in Shade and Sharp and Anthony Simon So I the more that I thought about it um this made a lot of sense to me if you’re Portland and that’s probably me being biased because uh I I I’m on the broadcast for that
Total shill
Total shill Uh but I mean 29year-old Fred Van Vleet joining the Houston Rockets They went from a 22- win team to a 41- win team to the number two seed in the Western Conference Uh Pat Bev joined a 23- win team for the Minnesota Timberwolves And of course Mike Connley again later uh developed them into a Western Conference powerhouse alongside Anthony Edwards The Blazers don’t have an Anthony Edwards right now They don’t have uh an Amen Thompson kind of Alfie Shangun kind of core yet but Danny Abdia I think has the upside of being an all-star next season He was playing at an all-star level in the second half of next year And now with the leadership and and uh mentorship of Drew Holiday and you get Rob Williams the third in there as well I just think that locker room is is vastly improved What are your thoughts on the Boston side of things because right now Anthony Simons is a $28 million expiring contract for the Boston Celus They shave some about $5 million off of the cap but that translates to about 40 million in luxury tax payments They’re still not below the second apron which kind of un unlocks a future first round pick Uh they’re not below that quite yet But Dan uh the player that Anthony Simons brings to that system I think makes a lot of sense Yeah the idea of give me a guy who is a super accurate quick trigger high volume three-point shooter in Joe Missoula ball like that that’s a handinand glove fit right especially you figure like the Celtics we saw what that that offense can look like without Jason Tatum and it can be touchandgo right like he he is such has been such a consistent engine of everything they do offensively year in and year out they are not going to have him next year the you the and it remains to be seen what additional moves are going to be made there but I think it’s reasonable to presume you’re probably going to try to keep Jaylen Brown and Derek White unless you get bowled over with an offer there So if you’re going to kind of have a time share with those two guys handling the ball more you don’t necessarily need Anthony Simons to be a primary ball handler shot creator running all the pick and rolls right you can have him be an offball player you can have him be a floor spacer running off pin downs and secondary actions coming off dribble handoffs all that kind of stuff And the way he can shoot off the catcher off the bounce feels like a really snug fit for what they’re going to need as somebody to like soak up usage soak up shot opportunities and just like with the like neon green light that you imagine Joe Misoula is going to you know put in for him in Boston Like that that feels pretty it feels like a really nice fit there And then like as we mentioned sort of this is the like the positive spin of the the Blazers maybe looking at it and saying we got if we don’t know that we feel confident in what Anthony is going to be for us moving forward it’s better for us to make a move now and move off him then like risk losing him for nothing in free agency The Celtics basically get to look at it and say here’s a year of data of what he looks like in our system Do we think that this translates to whatever the version of our team is when we have Jason Tatum back do we think he’s maybe like a high-end third or fourth option on that team or do we think that maybe the defensive liabilities with some of the concerns that we’ve got there make him somebody that we don’t want to keep around long term well you got a dice roll You got an opportunity to figure it out over the course of the next year You have his birds his bird rights to be able to either extend him or you know offer him more than anybody else in free agency next summer Or you can walk away and say like that coming off our books helps us as we try to continue lowering our overall you know luxury tax liability and getting you know dealing with the aprons moving forward for whatever the next competitive iteration of this team is going to be I I think that like in the context of the Celtics as they exist right now this feels like the first step in the larger project of chop down that bill get under the luxury tax I think we we’re still continuing to keep an eye on Christoff Torzingis are still continuing to keep an eye on Sam Hower You know the the Celtics are going to continue to be open for business And then if they do hang on to Anthony Simons heading into the season if they don’t reroute him in something some other kind of deal I think it’ll be interesting to see like how competitive Boston is next season because like they are part of that chaos in the top of the East they could also be a benefactor or they could also benefit them if the other teams are still you know falling by the wayside and they they still have the core of a continually competitive group and Simons can elevate that offense a little bit Like who knows what their postseason possibilities look like next season So like I think it’s an interesting variable to introduce into their their structure there in Boston But I think that it’s it’s like cost savings and apron management and roster management you know like flexibility first and then like basketball-wise could be an interesting move for Boston too
He’s a great shooter man
Off the bounce and deep threes He learned under the best in Damen Lillard and the logo threes Logo Lillard He’s uh he’s one of the guys that over the last couple years as I’ve been doing those games he gets doubled so much and so much of the attack in the pick and roll they would just swarm him because the defenses were like “We’re going to make other guys on the team beat you.” And that’s not going to be the case when you got Jaylen Brown and Derek White on the other side And who knows what they’re going to do with Chris Sporzingis uh Al Horford but they just have a lot more weapons to kind of proof that like doubleroof and blitz proof Anthony Simons in ways that was was was a little bit more challenging for the for the Blazers So like he’s a great shooter I think the Celtics are just going to give him like you said the greenest of green lights Like I it wouldn’t surprise me if he took like a Anthony Edwards volume of three-pointers next season because what do you have to lose the guy can shoot off the bounce He’s got a a beautiful three-point shot and Missoula ball offense He’s going to get 12 13 threes a game I’m I’m pretty sure of that Um so it’s a it’s a flyer for them is like hey we got him on an expiring deal like you said Bird Writes and if it doesn’t work out you can probably flip him at the deadline to a team like Orlando He’s from Orlando and maybe if Orlando’s like “Yeah we need we still need more offense.” I think he is going to provide value If it’s not going to be the Celtics he can also be moved at the deadline uh for for the for the Celtics too So there’s there’s optionality on that as well I think to me this is also just big picture Dan Really important to hit The Denver Nuggets won the title and then they were like “Yeah KCP we’re we’re just going to let you go to Orlando.” the the Boston Celtics have that Jason Tatum injury and then they’re like “Yeah we’re gonna shed salary here in Drew Holiday and perhaps Chris Porzingis.” The staying power of these champions is the shelf life is not very long at all And I don’t want to totally ascribe this to the CBA I think a lot of this has to do with the injuries that happened to to Jason Tatum But it does feel like OKC going forward this is another thing where they can just be like “Yeah I mean we’re going to we’re going to have a really good shot at a dynasty here because the Boston Celtics last year were perhaps our biggest competition in in starting what seemed to be championship contention over the next five years And now Boston is kind of not waving the white flag but I think this is a gap year move in trading for Anthony Simons and saying we’re taking a flyer on this guy He’s coming into his prime He’s one of the elite three-point shooters off the bounce in the NBA and in our system he’s going to excel and we’ll see what what we get in terms of the tax and the second apron It’s going to be a little bit tricky to try to extend him long term But um man people weren’t thinking big things about Derek White in Boston until they got him into that system And now he’s one of the the best uh the best two-way guys in the league Not saying Anthony Simons is going to be a two-way guy sure but just put him in Missoula’s system and maximize that that that that talent This could end up really really nice for the Boston Celtics But yeah it’s going to be tough tough to see that the the Celtics have already dismantled that championship core uh a little bit sooner than people expected but with Jason Tatum unfortunately it’s a harsh reality in today’s NBA So yeah a very confusing trade I will say that Dan Uh and we expect to have a lot more coming in the next 48 hours as we lead up into the NBA draft
Goes and goes and goes and goes Yeah it goes This is the NBA It’s gonna keep going Um by the time this ends like uh I our producers have not told us that there’s a blockbuster trade but uh I feel like as soon as we hang up here in a couple moments it’s going to happen right it’s going to happen Dave
Oh no I got to go to the grocery store We can’t do any emergency shows We got to like let’s All right wrap us up Tom Get us out of here
Uh yeah so that’s the big number Drew Holiday for Afford Simons Our four contenders for next year An early look ahead at the 26 NBA Championship Uh congrats to the Oklahoma City Thunder the OKC Dobermans Uh sorry to see the Indiana Passers That’s right I said passers What an amazing season from them Yes sir Uh it is heartbreaking to see the Tyrese Hallebertton injury And one note on that I forgot to mention this earlier
I looked this up after the the game We had we had talked about the Indiana passers and how much they had passed the ball to win these games and how much more they were passing than OKC without Tyrese Hallebertton for the majority of that game The Thunder actually had more passes in game seven than the Indiana Pacers
Wow
They had 269 for the Pacers and the Thunder had 272 Three passes more than the Pacers just to give you an idea of the impact of that injury just completely changed the way that they play basketball in that game So uh Dan this was an amazing year I love doing the big number with you this year We had a lot of fun doing it Uh some some improv some scat some uh some some big pimping Jay-Z lyrics That was just A+ work by you Uh this was a really fun year So thanks so much for doing this Dan Um and also to our team behind the scenes Stone Emmy Mike the entire squad behind the scenes Uh thanks so much for making this podcast and this show a reality Please watch The Big Number on YouTube Subscribe on all of the platforms Rate us five stars Go tell your friends We’ll be back next week with another episode of The Big Number Until then

Tom Haberstroh and Dan Devine break down the Celtics-Blazers trade that went down late Monday night, sending Jrue Holiday to Portland and Anfernee Simons to Boston. Tom thinks the Blazers defense could be a hellscape for opponents next season.

0:00 Blazers trade for Jrue Holiday
4:45 How Holiday’s veteran presence will impact the Blazers
11:11 What does Simons bring to the Boston Celtics?

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