Reaction to Jrue Holiday for Anfernee Simons trade between Boston Celtics & Portland Trail Blazers

Reaction to Jrue Holiday for Anfernee Simons trade between Boston Celtics & Portland Trail Blazers

all right welcome to Hoops tonight here at the volume Happy Tuesday everybody Hope all of you guys are having a great week Well we got another NBA trade last night as the Boston Celtics made their first big shakeup of the summer sending Drew Holiday to the Portland Trailblazers for an exciting young lead guard and Anthony Simons as well as two second round picks We’re going to be breaking that trade down from the perspective of both teams Then Jackson’s going to come on the show He’s a big Celtics fan and he’s going to give his take We’ll go back and forth about it for a little bit then we’ll get out of here You guys know the drill Before we get started subscribe to the Hoops Tonight YouTube channel so you don’t miss any more of our videos Follow me on Twitter_JLT so you guys don’t miss show announcements Don’t forget about our podcast feed Wherever you get your podcast under Hoops Tonight it’s also super helpful if you leave a rating and a review on that front Jackson’s doing great work on our social media feeds on Twitter Instagram Facebook and Tik Tok Make sure you guys follow us there And last but not least keep dropping mailbag questions in the YouTube comments and we’ll keep getting to them throughout the remainder of the year All right let’s talk some basketball So in the deal the Portland Trailblazers get Drew Holidayiday and the Boston Celtics get Anthony Simons as well as two second round picks So Boston turns an older veteran role player into a younger lead guard We all know who Drew Holiday is and what he’s capable of And in the context of the current iteration of the Celtics when fully healthy he brings a ton of value and utility right but the second that Jason Tatum went down the way that he did it officially made all the sense in the world to look to move Drew Holiday for something more useful in the long run My initial gut reaction when I saw the trade was wow like this is going to be fun This instantly makes the Boston Celtics next year interesting in a way that they wouldn’t have been if they would have made moves more in line with bringing in draft compensation or more theoretical talent This is more of like a in one year we’re going to find out really quickly how well Anthony Simons because Anony’s right at the beginning of what you would consider to be the prime of his career in his mid20s right you’re going to get to see really quickly how well he fits in the Boston system in the Joe Missoula driving kick system It’s a perfect test of a theory We haven’t seen a lead guard in this system That’s not to say that Drew or Derek couldn’t play with the ball in their hands Derek White obviously ran a ton of action with Jason Tatum is an excellent pull up three-point shooter A very good passer out of ball screens but he doesn’t really bring like all of the wiggle and downhill force that you get from Anthony Simons right drew Holiday plays with a lot of power does bring some downhill force Certainly can hit higher difficulty shots in ball screens and things like that but he doesn’t have the the level of just wiggle and and pull-up shooting and stuff that Anthony Simons has Anthony brings a combination of downhill burst shifty ball handling and pull-up shooting that neither of those guys had So before we get to any of the specifics of Anony’s game I’m just excited to see this tweak in Joe Misoula’s drive and kick system Anthony brings a very different style even than what Jaylen Brown and Jason Tatum did So in a year where Tatum is unavailable where the Celtics don’t have championship expectations they can evaluate what it looks like to see this type of guard play in their system of matchup hunting drive and kick basketball modern four out spacing big spacing above the break all of those specific characteristics immediately makes the Celtics a very interesting watch next year So a quick description of Anony’s game for those of you guys who haven’t watched much of him over the years He obviously spent the entire beginning of his career alongside Damian Lillard This is something that stood out to me throughout watching a young Anthony in Portland He plays aesthetically a very similar style to Dame He’s a bigger more upright player He doesn’t have the level the overall level of first step quickness and athleticism that Dame had But you can tell that they did a lot of workouts together You can tell that Anthony idolized Aim And by the way he picked a great player to idolize He’s got a very quick and compact jump shot release that he can get to out of all of the same kind of footwork stuff that Dame uses like hard pound dribble in and out to the right step backs going to the left step backs going both directions the mid-range pull-ups He’s got all of the same kind of like footwork and off the dribble jump shooting combinations that Damen Lillard had Again not to the same level of efficiency but at least in terms of the aesthetics and the way that he gets to his shots very similar out of hesitation dribbles out of dribble combinations from three and from the mid-range It’s like watching a taller Dane It’s legitimately crazy how similar their jump shot form and some of their body movements are He has all of the shot making you need in pick and roll pull-up twos pull-up threes floaters He can get to the rim He can make basic passing reads in pick and roll He’s not some surgical playmaker by any stretch of the imagination but he can make the reads that you need to run an NBA offense His weakness and this is in all likelihood why Portland is moving on from him hotels in Vegas may be booked that he isn’t particularly great at any of those specific things within the lead guard archetype like he’s a good three-point shooter off the catch but he’s not a great three-point shooter off the catch He’s a decent pull-up shooter 47% on pull-up twos last year 35% on pull-up threes It’s also worth mentioning he did go down year-over-year as a shooter but the previous year he spent mo the majority of the year playing alongside Damen Lillard catching lesser perimeter defenders So I do think that those two things are related in a lot of ways But again he’s a good pull-up shooter He actually got up over a point per shot but he’s not like some deadly efficient pull-up shooter like you see at the top guys in the league right he’s okay on floaters He’s 40% But that’s not the super high level floater shooter that you see around the league Guys like Ty Jerome Tyrese Hallebertton that are shooting over 50% on floaters He’s a decent driver of the basketball He’s particularly good at beating slowerfooted bigs and switches which I think will be uniquely valuable in Boston’s system But he’s not an elite driver of the basketball that like shreds defenses He logs about nine drives per game For perspective Shay Gilas Alexander 21 Brunson 18 Trey Young 17 He’s just not a great driver of the basketball the way that those guys are He’s a decent passer out of pick and roll and ISO but he’s not a super highle playmaker And then he’s got a couple of areas where he’s kind of weak right he’s very poor finisher at the rim Just 54% overall just 52% on layups He does have a little bit more vertical pop than you’d probably think And he’ll occasionally get up and throw one down but that’s not rim finishing is not a strength of his And he is not a good defensive player Although he did average a career high in steals last year The Portland Bla uh Trailblazers towards the tail end of the season took on more of a defensive identity you know behind guys like Tammani Kamar Robert Williams Matis Thybel Uh and by the way Drew Holidayiday is gonna be very interesting in that regard if they do decide to keep him but and Anthony did force more turnovers within that context but that’s not exactly what you would consider to be a strength for him The reason why I like this move for Boston has to do with their culture has to do with the brand of basketball that they’re playing Anony’s flaws all those things that I just went over are what made him inexpensive to get in a trade He’s due an extension soon Obviously whether or not that extension meets a certain threshold uh uh is is going to be a big part of whether or not this makes sense for Boston but they could also turn around and flip him If he goes in there this year and you know you set him up properly and in the Boston system and it just continues to be underwhelming they can turn around and flip him They can turn around and move him in a different direction And so obviously there’s a forwardthinking element to this in terms of asset management What they do they retain him uh if they do what do they retain him on in terms of an extension if they move him what do they get in return that is going to be the kind of like swing factor in this deal But you know that’s on Brad Stevens to figure out in the short term You gave yourself an opportunity to see what Anthony Simons looks like in this system Boston is one of the best teams in the league at creating space for drivers of the basketball Some of the little things that they do in terms of like spacing bigs above the break to create uh different sort of help defense situations So instead of there being a big waiting at the rim the big is out dealing with you know Porzingis or Horford above the break And now you have a small guard Someone like a Derek White someone like a Payton Pritchard someone like a Sam Hower sometimes drifting into the dunker spot So that the help defender the guy guarding that guy is a smaller player that’s contesting at the rim They move without the ball They’re constantly cycling through There’s a lot of things that Boston does to create really open areas on the floor for guys like Annefernney to go to work Now obviously it remains to be seen whether or not some of those guys get moved So like if you know they don’t bring Horford back and then they trade Porzingis then yeah it’s going to potentially have an impact on their spacing But even in that context dating back to 2022 when they were playing some of these non-shooting bigs like Robert Williams they are capable of generating space And I think that that’s a very interesting spot for Anthony to be in He’s also going to be surrounded with more like dribble shoot pass talent than he was surrounded by in Portland He’s going to be in lineups where Jaylen Brown’s on the floor where Derek White’s on the floor where Hower’s on the floor where Pritchard’s on the floor where Baylor Sherman’s on the floor He’s going to be in situations where he is getting the ball in advantages and he’s creating advantages for his teammates in that drive and kick system It’s an awesome opportunity for us to see just a different guy Now like we talked about because their guards weren’t this type of guard and because Tatum and Brown are these big matchup attacking forwards that as we’ve talked about over the years can sometimes settle for jump shots and struggle to beat their man at the point of attack I’m interested to see if this Boston offense is a bit more resilient with more of a lead guard that they can go to to get dribble penetration to start the engine when things get kind of stagnant Anony gets up into that high hesitation dribble and he will pressure those gaps and he will get into the teeth of the defense And so there is a different look there that I think will be really interesting I like the move It makes Boston a more interesting watch this year It’s kind of like an opportunity to get a different look at the Celtics offense with a different archetype of player And then one of two things will happen Either Brad Stevens will move him for asset return to help Tatum and Brown when Tatum gets back from his injury or it’ll be like “Oh this works Now let’s talk about what we’re going to look like in the future in a system that involves both an Anthony Simons and Jason Tatum and potentially Jaylen Brown as well It is an awesome opportunity to run an experiment and see what this player looks like in the most advanced drive and kick system that we have in the NBA right now I’m very very excited to watch it On the Portland front I would assume this is about opening up some ball handling responsibility about opening up a starting spot Scoot Henderson has done a lot of coming off the bench since he’s been drafted This is a situation that should open up more lead ball handling responsibility for him more ball handling opportunities for guys like Denny Odia who showed some off the dribble pop towards the tail end of the season I’m just wondering whether or not they have any plans to actually use Drew Holiday in the short term or if they intend to flip it I feel like Drew is most valuable on a roster that is championship capable where he can push a team over the top and that’s not really what Portland is But there is kind of this growing feisty defensive attitude that Portland took on towards this you know second half of the season or so as they started to rack up a few more impressive wins than usual A couple of those like two week streaks were like “Oh man Portland’s beating some people This is interesting right?” Like Tumani Kamara coming around as one of the better young wing defenders in the league Robert Williams when he’s healthy is still a very really impactful switching big and rim protecting big Matis Thybull has been one of the better defensive wings in the league for a long time Drew Holiday should fit into that context extremely well in terms of helping them It just doesn’t help them get to what their ultimate goals are And so that’s why you know I I kind of would have preferred to see Drew go to more of a contending team But it’ll be an interesting kind of influx of defensive culture for that roster All right Jackson So you’ve had about a little over 12 hours to think about this deal As a Celtics fan where are you at with Anthony Simons becoming a Celtic what’s a really fun flyer There’s the they haven’t had a player like this in a while It we’ll see what else they do this summer You know I don’t think this is the last move for the Celtics this summer But it certainly is a fun bridge option where if it really hits in a way that maybe even higher than I’m expecting then all of a sudden in in an East with all these injuries like maybe the Celtics are actually way more competitive than we may have thought after the Tatum injury And if it doesn’t hit then it’s like okay that’s kind of what we were expecting anyways It’s sort of this sort of middle to middle down year for Boston The contract situation is a is has some upsides and has some downsides I mean the the fact that it’s expiring makes definitely an a tradable piece potentially at the deadline if if he’s playing well and the Celtics don’t want to be competitive or don’t want to be as competitive Um if he really plays well though I’m would be curious what number they’re comfortable extending him at You know like if it really hits which there’s they’re going to need offense And so it’s certainly possible that he averages 24 points a game or something like that I think that’s definitely within the realm of possibility And if that happens I’m not sure what number you’re comfortable signing him at considering he’s not a plus defensive player and Missoula ball while it’s sort of most people think about it offensively and it is it’s also a lot of we want all of our players to be two-way players you know what I mean so that’s the one one of the question marks I think but overall just zooming out I I really like it for Boston I think it’s a little weird for Portland but you know they’re they want to be a great defensive team and this is going to help with that so I get that yeah the the the big key is going to be just how good he is right away Like is this a is this a oh an underutilized lead guard playing in clunky spacing on a defensive-minded set of role player core for a you know kind of an inexperienced relatively new head coach that hasn’t had any success yet in the NBA like is this is that what’s going on here or is Anthony Simons just not that level of guard and we are going to find out I can I feel like in that Eastern Conference which is pretty open and alongside that group like again like they’re going to make some moves this year but like you can count on Cornet being there You can count on Jaylen Brown being there most likely Payton Pritchard Sam Hower Derek White Like there’s they’re going to be still a good core of Celtics role players around him Yeah In a system where these dudes have been playing this style for a long time And like to me I think the indicator will be like the scoring plus the efficiency Like if they’re if they’re sitting at the All-Star break and he’s at like 62% true shooting because he’s been hitting 40% of his pull-up threes and like his drives have gone up from 9 to like 13 per game because they’re just creating more space and all of a sudden like it’s just coming together in a way That that is where I I think you start to look at it like oh we are actualizing this player for sure And now he makes sense in this context And I think honestly to your point about the East being open that might literally be the best case scenario If you could get like two playoff rounds out of an Fernie and kind of see him in that setting I I in that context I think that could be super interesting Yeah I mean I think the he he’s immediately the second most skilled offensive player on the roster I mean I like Derek White a lot but he’s his his overall value is in part because he’s a two-way player I think Anthony Simons is immediately the second best offensive player And and that’s a little strange Like it’s it’s it’s a unique context to go into a team that was so it felt like perfectly built and now you have to just retool obviously after the Tatum injury but I think this is as good of a pivot as you could make consider in the short term It’s it’s not what I was expecting in the Drew Holiday deal I’m going to say that I was expecting a Dallas Mavericks get a first round hopefully get a f like there was some mixed reporting whether that it was going to be the Celtics need to give up assets to get off of that contract or is the value good enough we can get assets back It was sort of mixed reporting in that sense I wasn’t really sure what his value was and I was definitely not expecting a young player in return I was expecting picks really um or or a young player like a young player who’s you know developed enough at this point I was maybe would have been a young flyer or something But I think it’s fun and I I think that you could talk yourself into a lot of different outcomes considering how unstable the weak feel the east unstable the east feels right now The the usage piece is the interesting part Like to your point I I thought that we would see a couple of different types of moves from Boston this year in terms of bringing in younger role player talent draft compensation things that would allow Brad to effectively pivot around Tatum and Brown next year That that’s that’s what I was expecting too And like it’s just that that’s what I meant when I said like oh Boston became so much more interesting Anthony can come in and be high usage Like I I’m not Now whether or not it ends up being consistent will be the key right but like you will have games next year where Anthony drops 35 and lights the uh lights the TD Garden on fire and everyone’s like “Oh my gosh look at that.” Like he will have awesome highscoring massive games like he had that famous game winner driving past Russell Westbrook this year against Denver Like he is a guy that has real upside It’s it hasn’t come to fruition over the course of his career but I kind of like this I like uh Bill Simmons used to talk about this on his show all the time and it’s kind of an interesting concept It’s like lottery flyers So like people who were picked in the lottery that struggled in their first destination that uh maybe you just think oh we get him into a new kind of setting and this is a guy with some real pedigree with some real talent Maybe we can get it out of him This is kind of like a different version of that It’s more like in that after that second contract where it’s like he’s much more established but it’s a similar idea where it’s like we’ve only seen this guy in one construct It’s generally been a losing construct the entire time he’s been there We’ve seen him on super offensiveminded rosters where he’s put up big numbers but they can’t win Now we’ve seen him on defensive minded rosters where his efficiency tanks but like they were you know over 500 there for a big chunk of the season So like there it’s it’s kind of it’s just an experiment It’s an experiment And like in terms of the uh the compensation piece to your point like Drew Holiday was going to get you something He wasn’t going to get you a hall No he you know you weren’t going to get three first or so like a really really good interesting young player Like to turn Drew Holiday an expensive older veteran player into a mid20s dude that you have can decide what you want to do with next to me is like a really smart pivot that makes you more interesting and it’s like a legitimate opportunity to like experiment for Boston’s future cuz again they were going to need to pivot They weren’t going to be able to just bring everybody back next year Horford would have been too old Porzingis would have been too old Drew Holiday would have been too old You’ve got to start experimenting with this right now Yeah 100% So I I think in that context it definitely makes sense And also being able to get not that I’m banging the drum for the value of second round picks or anything but Portland is trying to be competitive The West is loaded I would frankly be surprised if they even made the play Maybe they sneak into a nine or 10 spot So if they missed the playoffs that that second round pick could be pick 38 or something which is not you know crazy valuable but you get two of them from Portland which are decent dart throws or decent little asset you know fillers you could throw into other deals So overall I think value-wise I’m happy with it I think it’s a re it’s a way to make the team a lot more I I was really kind of expecting a complete sort of dump of a year like a punt of a year and it’s definitely not going to be that with a move like this You’re not you’re certainly not saying we’re punting on the season You’re trying to like let’s try to let’s see if we can be fun and competitive especially in in a down east And Jaylen Brown is going to be attacking this off season preparing for his first full season as a lead ball handler You know Jaylen Brown’s going to come in in great shape He’s going to dictate most likely the best perimeter defender on most nights which will help put Infern back into a situation like he was in with Dame There’s a lot of like inverted stuff he can do with Jaylen It’s I’m just excited I’m excited for open like the opening week and like seeing what the Celtics team looks like and I just didn’t think that was going to be the case down the way that he did It’ll be really weird I still have no idea You know they got a lot of moves to make I think what the front court is going to look like No idea what the front court is going to look like but Drew uh sorry Derek White Anthony Simons and Jaylen Brown is a very fun sort of trio going into going into next season I think from a back court wing standpoint Totally agree Totally agree All right guys That’s all we have for today As always we sincerely appreciate you guys for supporting us and supporting the show If you didn’t see it we did drop like an hour and a half of draft content with Samini this morning Uh you guys can find that a little bit further back on our feeds We will be back tomorrow night live during the NBA draft Uh we’ll have some information on Twitter today about uh exactly when we’re doing that I’ll keep you guys posted but it’s going to be basically right after the lottery We’ll do our uh draft reaction and then we’re also going to have some mailbag stuff later in the week It’s going to be a fun week of content We appreciate you guys for supporting us We will see you tomorrow

Jason reacts to the trade between the Boston Celtics and Portland Trail Blazers, swapping Jrue Holiday for Anfernee Simons and two second round NBA Draft picks. He discusses why it’s a fun flier for Boston, how Anfernee can pair with Derrick White and Jaylen Brown, and what the Celtics goals are during this down year without Jayson Tatum. He also breaks down the Portland side, why it’s a little more confusing what they’re doing, and whether or not they should keep Holiday alongside Scoot Henderson.

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