Hoops Tonight - Reaction to Jrue Holiday traded from Celtics to Trail Blazers for Anfernee Simons

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a great week. Well, we got another NBA trade last night as the Boston Celtics made their first big shakeup of this summer, sending Drew Holiday to the Portland Trailblazers for an exciting young lead guard and Anferny Simons as well as two second round picks. We're gonna be breaking that trade down from the perspective of both teams. Then Jackson's gonna come on the show. He's a big Celtics fan. And he's gonna give his take. We'll go back and forth about it for a little bit and then we'll

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So in the deal, the Portland Trailblazers get Drew Holliday and the Boston Celtics get Anferny 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 Holliday 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.

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 Anfernie Simon's Because Anthrony's right at the beginning of what you would consider to be the prime of his career in his mid twenties, right, You're gonna get to see really quickly how well he fits in the Boston system, in the Joe Mizula driving kickses them. 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 Jayson Tatum as 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 an Anfernie Simons. Right, jew Holliday 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 level of just wiggle and pull up shooting and stuff that Anthony Simons has. Anfernie 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 Anfernie's game, I'm just excited to see this tweak in Joe Mizula's driving kick system, and he brings a very different style even than what

Jalen 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 Anferny'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 esthetically 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 Anthny idolized Dame, 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.

movements are. He has all of the shot making you need and 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 strike 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, is 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 forty seven percent on pull up twos last year thirty five percent on pull threes. It's also worth mentioning he did go down year over year as a shooter, but the previous year he spent the majority of the year playing alongside Damian Lillard catching lesser primitive 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 forty percent, but that's not the super high level floater shooter that you see around the league, guys like Tydrome, Tyree s Haliburton that are shooting over fifty on floaters. He's a decent driver of

the basketball. He's particularly good at beating slower footed 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 Gilges, Alexander twenty one, Brunson eighteen, Trey Young seventeen. He's just not a great driver of the basketball the way that those guys are. He's a decent passer at a pick and roll in ISO, but

he's not a super high level 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 fifty four percent overall, just fifty two percent 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 and steels last year. The Portland Trailblazers towards the tail end of the season took on more of a defensive identity, you know, behind guys like Tamani Kamara, Robert Williams, Matist Thaibel and by the way, Drew Holliday's going to be very interesting in that regard if they do decide to keep him. But and Anthrony did force more turnovers within that context, but that's not exactly what you would consider to be a.

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 forward thinking element to this in terms of asset management. What they do they retain him, 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 Zimons 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 a different sort of help defense situation. 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 it Derek White, someone like a Peyton Pritchard, someone like a Sam Hauser, sometimes drifting into the dunker spot, so that the help defender the guy guarding that guy as 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. Four guys like anfernit 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 twenty twenty two 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 Anferni to be in. He's also going to be surround with more like dribbles shoot pass talent than he was surrounded by in Portland. He's going to be in lineups where Jalen Brown's on the floor, where Derek White's on the floor, where Houser's on the floor, where Pritchard's on the floor, or Baylor Shireman'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 forts 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. Anthony 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 shit,

this works. Now, let's talk about what we're gonna look like in the future in a system that involves both Anthony Simon's and Jason Tatum and potentially Jalen Brown as well. It is an awesome opportunity to run an experiment and see what this player looks like in the most advanced driving kick system that we have in the NBA right now.

tail end of the season. I'm just wondering whether or not they have any plans to actually use Drew Holliday 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 the 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 where we're like, oh man, some people this is interesting, right, Like Timani 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 matist. Steibel has been one of the better defensive wings in the league for a long time. Drew Hollidays 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 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 twelve hours to think about this deal. As a Celtics fan, where are you at with Anthony Simon's becoming a Celtic?

It We'll see what else they do this summer. You know, I don't think this is the last MOVI 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 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 has some upsides and has some downsides. I mean, the fact that it's expiring makes definitely an a tradable piece potentially at the deadline if he's playing well and the Celtics don't want to be competitive or don't want to be as competitive.

If he really plays well, though, I would be curious what number they're comfortable ex sending him at, you know, like, if it really hits, which there's they're gonna need offense, and so it's certainly possible that he averages twenty four 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 can I feel like in that Eastern Conference, which is pretty open and alongside that group, like again, like they're gonna make some moves this year, but like you can count on Cornette being there, you can count on Jaln Brown being there, most likely Pet Peyton, Pritchard, Sam Houser Derek White, Like there's they're gonna be still a good core of Celtics role players around him 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 sixty two percent true shooting because he's been hitting forty percent of his pull up threes, and like his drives have gone up from nine to like thirteen 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 think you

start to look at it like, oh, we are actualizing this player, 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 Anferny and kind of see him in that setting in that context, I think that could be super interesting.

as you could make consider in the short term. It's it's not what I was expecting to Drew Holliday deal. I'm going to say that I was expecting a Dallas Mavericks get a first round, hopefully get it. Like there was some mixed reporting whether that it was going to be the Celtish 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 or a young player, like a young player who's you know, developed enough at this point. Maybe it would have been a young flyer or something. But I think it's fun and I think that you could talk yourself into a lot of different outcomes considering how unstable the Weak feel the East unstable the East fields Right.

Anferny can come in and be high usage. Like I'm not now whether or not it ends up being consistent will be the key, but like you will have games next year where Anferny drops thirty five and lights the lights the TV garden on fire, and everyone's like, oh my gosh, look at that. Like he will have awesome, high scoring, massive games, like he had that famous game winner driving pass Russell Westbrook this year against Denver. Like he is a guy that has real upside. It's hasn't

come to fruition over the course of his career. But I kind of like this like Bill Simmons used to talk about this on his show all the time, and it's kind of an interesting concept.

one construct. It's generally been a losing construct the entire time he's been there. We've seen him on super offensive minded rosters where he's put up big numbers but they can't win. Now we've seen him on defensive minded rosters or his efficiency tanks, but like they were you know, over five hundred there for a big chunk of the season. So like it's it's kind of it's just an experiment.

It's an experiment. And like in terms of the the compensation piece to your point, like Drew Holliday was going to get you something he wasn't going to get you a haul, you know, you weren't gonna get three firsts, or like a really really good, interesting young player. Like to turn Drew Holiday, an expensive, older veteran player, into a mid twenties dude that you 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, because 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.

Maybe they sneak into a nine or ten spot so if they missed the playoffs, that that second round pick could be picked thirty eight 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.

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 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 content. We appreciate you guys for supporting us. We will see you tomorrow.