Brian Robb and Souichi Terada of MassLive.com break down the surprise trade of Damian Lillard to the Bucks along with the domino effect on the Celtics and the rest of the Eastern Conference. The guys then turn their attention to Jrue Holiday who is readily available on the trade block after the Lillard deal. What would the Celtics have to give him to get him? Would it be worth the risk or are the Celtics better off pursuing a different target?
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SportsTranscript
00:00 I guess my big concern is how he's going to look and you know, eat the East finals and
00:03 beyond.
00:04 Right.
00:05 Like that's a very long season and it's just not guaranteed that this 33 year old guy is
00:08 going to be able to hold up.
00:09 So that's just, I have a lot of questions, you know, obviously, right.
00:12 Like Janice was kind of hinting that he might leave.
00:14 So I totally respect the books from an office or swinging for the fences is doing what they
00:18 did.
00:19 And like you said, like they only had so many assets to give out or to trade and they're
00:23 pretty much depleted now.
00:24 So, but in terms of, you know, how all the pieces fit, this should be fun though.
00:29 Don't be robbed.
00:30 Like November is, is I forgot the exact date, November 22nd or whatever.
00:33 First Celtics box games of the season at Boston, the first of four.
00:37 And that should be a lot of fun.
00:38 I'm just, we'll, we'll see how it all, how it all works out.
00:41 Like I'm, I'm super excited though.
00:43 Like basketball season is right around the corner.
00:45 Like we're about to flip in October.
00:46 Like this should be a lot of fun.
00:48 Winning plays is brought to you by FanDuel, the exclusive wagering partner of the CLNS
00:53 media network.
00:54 All right.
00:55 Winning plays podcast back yet again.
00:58 What was supposed to be the calm before the storm of NBA training camp, but no, that is
01:04 not happening.
01:05 We are not going to go into the season quietly.
01:06 Sweetie Tirada of MassLive.
01:08 We're coming in with a blockbuster, Damian Lillard going to Milwaukee, Miami coming up
01:15 empty handed, and now one more star readily available on the market in Drew Holiday right
01:22 there.
01:23 I guess, first off, what's, what's your reaction to this sequence of events here that, that
01:27 the bucks kind of come out of the woodwork and then, and steal Lillard from the heat
01:32 and a bunch of other interested parties?
01:34 Yeah, well, first and foremost, B-Rub, I would much rather take a blockbuster NBA trade,
01:39 my jaw dropped personally, but I would much rather take that the Wednesday before training
01:43 camp compared to last year, which I believe was what, like the 11 PM Eastern time kind
01:48 of deal.
01:49 I was in Arizona, I think.
01:50 So I was a few hours ahead, but I was like, oh, okay, I guess we're doing this email thing
01:54 now.
01:55 So more subject matter to talk about than, yes, illegal, then not illegal, inappropriate
02:00 workplace conduct.
02:01 Yes.
02:02 Very, very happy that we're talking basketball instead of anything else right now.
02:06 On less than a week before training camp.
02:09 Yeah.
02:10 But like I said, B-Rub, I don't know, my jaw dropped.
02:11 I feel like pretty much all indications was that it wasn't going to be Miami.
02:15 I know Celtics fans were a little bit worried, but it seemed like one of those deals where
02:20 the Pelt or the Trailblazers didn't really want to trade with, with Miami and everything.
02:24 The Raptors seemed like a good team, but the Bucks, man, I don't know.
02:27 Like that's crazy to me.
02:28 Like I said, my jaw dropped in the sense of like, just trying to fit all the pieces in
02:31 together.
02:32 I mean, the Drew Holliday, I know we're going to get into it, but just you lose a piece
02:35 like you holiday.
02:36 He's so important.
02:37 But then you add a Damian Lillard, right.
02:39 And I thought, and I'm sure we'll get into a little more and I want to hear your thoughts,
02:43 B-Rub, but just, I'm so curious to see how the Bucks will look right.
02:47 Like they'll have a first year head coach like Dame, obviously, right.
02:51 Amazing player, all world players, superstar.
02:55 I thought, you know, especially when the, with the injuries, Chris Middleton and everything
03:00 like that, like the Bucks didn't really have a great number two options, scoring options,
03:03 because Drew can be that guy, but he can't be that guy night in and night out.
03:07 Whereas now you have a number one option and Dame and maybe a little bit, a lot more of
03:11 the scoring burden won't have to come from Giannis and everything.
03:13 So, but you look at it defensively, you lose a guy like Drew, you know, you think of a
03:18 Celtics Bucks playoff matchup and like, who's going to guard Jason and Jalen, right?
03:23 Like you no longer have a Drew Holiday type.
03:24 So Pat Connerton added, right.
03:27 You don't even have a Grayson Allen anymore, right?
03:31 Malik Beasley, Jake Crowder, they've not yet.
03:34 No, it's no, you know, it's like they're betting, they're making the big bet on offense over
03:38 defense.
03:39 And I mean, obviously there's still plenty of time to, for them to adjust the roster
03:43 as they go here, but their, their assets are pretty sharply depleted here.
03:48 I don't even know if they have any future first left to move period.
03:54 And player wise.
03:55 Yeah.
03:56 You're like, who's going to stop a Lillard Giannis pick and roll.
03:59 Like, I don't know, but also who is going to stop, like you said, who's going to stop
04:03 Tatum Brown or anyone else in the, in the East on the perimeter.
04:07 And so it is like, it's a fascinating, you understand why the Bucks did it since Holiday
04:16 as like a number two is clearly like, wasn't good enough for them offensively the last
04:21 couple of years with Milton not being himself.
04:23 But now they're going to be stretched to the bring on defense, but it might not matter
04:28 if they're outscoring teams, if they're scoring 120 points a game.
04:31 Yeah.
04:32 And I just, one big concern I did have with Dame is just he's, he's not, he's 33 years
04:38 old and he's had durability, really injury concerns the past few years.
04:42 And I'm just a little bit concerned about how he's going to hold up throughout the season.
04:46 Obviously the Bucks can do what the Celtics have done with a Malcolm Brockton and Al Holford
04:51 and Rob and, and, you know, what they will do this season, but it's just that that's
04:55 all, you know, that's an old guy.
04:57 I'm just a little bit, I guess my big concern is how he's going to look and, you know, eat
05:01 the East finals and beyond, right?
05:02 Like that's a very long season and it's just not guaranteed that this 33 year old guy is
05:06 going to be able to hold up.
05:07 So that's just, I have a lot of questions, you know, obviously, right?
05:11 Yannis was kind of hinting that he might leave.
05:13 So I totally respect the Bucks from an office or swinging for the fences is doing what they
05:17 did.
05:18 And like you said, like they only had so many assets to give out or to trade and they're
05:21 pretty much depleted now.
05:23 So, but in terms of, you know, how all the pieces fit, this should be fun though, be
05:27 robbed like November is, is I forgot the exact date, November 22nd or whatever first Celtics
05:32 Bucks games of the season in Boston, the first of four.
05:36 And that should be a lot of fun.
05:37 I'm just, we'll, we'll see how it all, how it all works out.
05:40 Like I'm, I'm super excited though.
05:42 Like basketball season is right around the corner.
05:43 Like we're about to flip in October.
05:45 Like this should be a lot of fun.
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06:21 No, I mean, it's going to be a straight up arms race coming up here.
06:29 Because when you have the Bucks making this type of chess move to start the year, then
06:33 every team, including the Celtics, have to take a hard look at themselves and be like,
06:37 "Okay, we like our team.
06:38 Do we love our team?
06:39 Do we think we match up well enough against these teams to get over the hump here?"
06:47 And with all these teams being very much now in the win-now window, the pressure is on.
06:53 You can't say, you know, you can't plan on a year here and there.
06:56 The Celtics have obviously seen opportunities slip away, great opportunities slip away in
07:01 the last couple of years.
07:02 And now the road on paper looks tougher.
07:07 And that's something that we weren't necessarily the case like a week ago now.
07:11 So that's going to cause all these teams to look at themselves.
07:15 And I do honestly, like, we'll spend plenty of time on other stuff, but I think the pertinent
07:18 stuff now for the Celtics and the rest of the East is this Drew Holiday situation, which
07:22 I think is really worth diving into since the whole world knows that he's available
07:27 after the Blazers picked him up.
07:30 They're going to keep DeAndre Ayton, it sounds like, a younger guy, a guy that they, I don't
07:35 even know.
07:36 I mean, we can talk about the Blazers later, but this is like, it's kind of, they did weird
07:39 stuff here.
07:40 I'm not exactly sure what to make of it, but they obviously are going to try to turn Drew
07:44 into a lot more stuff for them.
07:47 And the Celtics are one of several interested parties there.
07:51 What say you about just in general, like the going for Drew Holiday versus the cost of
07:58 acquisition here for the Celtics in this set scenario?
08:01 Yeah, I mean, B-Rob, we did a great job on MassLive this morning, just kind of breaking
08:04 down the numbers, the contract number, right?
08:06 Like everyone wants to throw Malcolm Barker and some picks into a trade, but that's not
08:09 how salaries work in the NBA, salary cap and all that good stuff.
08:14 So yeah, I mean, I thought you did a pretty good job of laying it out in terms of like,
08:18 this doesn't really make sense, it seems like you're going to have to include a Malcolm
08:22 plus a Rob.
08:23 It's just, I feel like that's a non-starter for the Celtics and who they are.
08:27 I do wonder if the Celtics offseason looks very different at the Dane trade happen, say
08:32 around the draft or so.
08:35 And then, you know, like, do you let a guy like Grant and Marcus walk, right?
08:39 Like, especially because you're going to want more defensive juice.
08:42 You look at a Porzingis type in, right?
08:43 If the Celtics play a little bit more drop coverage, playing against a Dame Giannis pick
08:47 and roll isn't exactly, that's not exactly ideal, right?
08:52 A lot of stuff, Curry in the 2022 NBA finals kind of shades of that a little bit.
08:57 So, but it just seems like Drew with his age, like I believe he's also 33, like he doesn't
09:01 really necessarily fit the Celtics core.
09:04 And it's just, it's just one of those things, like I understand, you know, the Celtics should
09:07 do their due diligence and everything, but it's just, it's, this doesn't seem like it's
09:10 going to make much sense, especially if they're going to get into a bidding war with other
09:13 contenders.
09:14 And that's kind of what you laid out, B-Rob, I thought on the outside earlier today.
09:18 Yeah, it's, it's because it is like, this is a guy that they wanted years ago and the
09:24 Bucks got them and the Bucks won a title from.
09:27 So it's like, okay, yeah, like that's like, it's kind of crazy that that's happened already.
09:31 And then they've already flipped them again.
09:33 And it's like, that's like the, the life cycle of the NBA here where it's like, okay, like,
09:38 you know, you're not, you're not set for life here after you win a title, even like whatever
09:43 was three years ago.
09:45 Like, nope, we actually, we need to get better here again.
09:48 And we're going to use you to do it.
09:51 I mean, this guy was like, I want to retire.
09:53 Yeah, right.
09:54 What was this quote?
09:55 Was that like last month that he was talking?
09:56 No, I thought it was literally yes, like two days ago.
09:59 Oh my God.
10:00 It probably wasn't two days ago, the interview, but it was very recent.
10:04 Which is just, I mean, at the same time though, right?
10:06 Like when we heard about the Chris Southbury-Zingas deal, initially, we thought Michael Brogdon
10:11 was gone, which felt very natural.
10:12 And then close to midnight, Marcus Smart is gone.
10:14 Right.
10:15 So it's just, that's just how the league goes unbelievably sometimes.
10:20 And so like, from that standpoint, like you can make a case for it from like, okay, a
10:25 closing lineup of like Drew Holiday, Derek White, Brown, Tatum, and whatever bigs left,
10:32 Porzingis or, you know, Horford.
10:34 Like that's, that's pretty damn good.
10:36 Like that's probably the best closing five in the NBA.
10:40 Like, you know, top to bottom, pretty easily there.
10:42 Is it the perfect one?
10:44 Like not necessarily, but it like that covers all your bases.
10:49 With that said, your depth in the front court, it's just, I think for me, it's like the whole
10:54 depth in like in the front court of like, you let Grant walk.
11:00 So now you have Porzingis, who is reportedly, you know, good to go for camp here.
11:06 Al and Rob, and that's it.
11:09 You even take one of those guys out of the equation, period, and you go down to Luke
11:12 Cornett on the depth chart chain.
11:16 Like that puts you in a pretty vulnerable spot if just one of those guys gets hurt,
11:22 which is almost a guarantee to happen this year for like, given their, their tracker
11:26 there.
11:27 So then it's like, well, is Holiday that much better to like, to mitigate that risk?
11:31 Like, are you going to be okay if one of those guys going down, are you have enough leftover
11:35 to go get someone who can fill that spot with that, you know, the grantee be like, that's
11:41 to me, that's like, maybe they can, maybe they have something up their sleeve where
11:43 they can pull off that kind of a deal, Suichi, but like on the surface, I think that's might
11:49 be too much to try to pull off here, especially against what other teams are bidding.
11:54 Yeah.
11:55 And I think that's the biggest thing too, is that Brad Stevens has obviously not been
11:59 shy to trade away his, his first round picks.
12:02 But I thought that's looking at in the more short term in terms of like, right, trading
12:07 next year's pick or the past few years and everything, but like they've kept the cupboard
12:11 pretty stocked up besides that a pixel up with a Spurs.
12:13 And then, and then you kind of look at it and just like, hmm, okay.
12:17 It just seems like they're going to do their due diligence, but it's not necessarily going
12:21 to be something that they, that they push their chips all in for.
12:24 And I think that's, I think personally, be robbed.
12:26 Like, that's a smart thing to do.
12:27 Like you've already made your gamble this off season on Chris tops.
12:30 Like it doesn't, you don't like, obviously the, the Dave trade to the bucks changes things,
12:36 but I think you look at this roster and you're like, okay, well we've already made a big
12:39 swing.
12:40 Like, like, like that's okay.
12:42 Like it's, it's okay to kind of stand pat, especially if the drew holiday situation doesn't
12:45 make sense.
12:46 So I think you just look at it and you feel okay with where this roster is at.
12:50 As you said, the injury concerns are very big.
12:52 I just think that is too big of an issue, especially over the long regular season going,
12:56 you know, we like the playoffs are a long playoffs are long, man.
12:59 After two months long, that's why I'm kind of concerned with the Dave situation in terms
13:03 of like, will he be able to hold it?
13:04 Like, well, it's supposed to be able to hold up.
13:06 So there's taking away from that.
13:07 That does not necessarily, I think to move.
13:09 And I think that's kind of where we're at.
13:12 Right.
13:13 And, and that's just how it is.
13:15 Like, like I said, maybe they keep, maybe they try to hold out the markets a little
13:18 bit more knowing that Dave is going to be in Milwaukee, but that's the past that, and
13:22 you just kind of have to live with it now.
13:24 Yeah, it's, I mean, that will be talked about plenty.
13:28 If, if they, if the Celtics get torched by game in the Eastern conference, semifinals
13:33 or finals like that, this is going to be a column that will be written many a time.
13:38 But it is, it's like, to your point though, if like the rod, like, yeah, if they took
13:42 their big string of prison, I guess, was that maybe too early?
13:45 We'll, we'll see.
13:46 But there is something to be said now for kind of seeing what it looks like before making
13:53 any, any other meaningful changes here.
13:57 And I do think the Celtics still have a swing to make in my mind, they only have one real
14:03 big swing left to take.
14:04 And that's with Brockton's like contract.
14:06 I mean, maybe Brian comes to camp and he plays great and everybody, the chemistry is great
14:10 and everything's fine.
14:11 Like, yeah, like that, that's totally possible that they, you know, ride out if, if this
14:15 group has something special going on and he's fitting in there.
14:18 But if not, if you want to say, okay, where can we, where do we need our next best upgrade
14:24 to lost or to create that, you know, perfect lineup to go up against Damon Giannis or Miami,
14:30 if they add another star here, like that's, you have to be able to do that.
14:35 And if you, if you bet on Drew now, then you literally take away that option for the rest
14:41 of the season here.
14:42 And that is something I think they need to like the organization, I feel like we'll probably
14:47 be looking at very closely here being like, okay, if we're going to spend this trade capital,
14:51 is this like the right guy to do it on?
14:52 Or is there going to be a better fit potentially that might become available in December or
14:57 at the trade deadline or whenever?
14:58 Yeah.
14:59 And I think that's just a luxury that the Celtics have in that it's a long season trade
15:03 deadlines until February, right?
15:05 That's still five months away.
15:06 So let's, let's, it's a great idea, I think, just to be patient and see what you've got.
15:11 And my big thing too, is like, you look at it, right.
15:13 The Celtics and Bucks look like the two favorites coming out of these.
15:16 Both teams at this point have a lot of question marks, not anything to be like, are they even
15:19 going to be title contenders?
15:20 Obviously, they probably will be, but it's just to see how it all fits out.
15:24 And I think just taking the patient approach is smart, because, you know, you never know,
15:28 right?
15:29 Like people are, I would love to see a Celtics, Bucks, East finals and everything.
15:32 Milwaukee in May is much nicer than in Christmas, for example.
15:36 But it's just, it's just one of those things where you just don't know.
15:38 The Bucks lost in the first round last year, the Celtics looked like they had an easy path
15:41 to the finals.
15:42 That wasn't the case.
15:43 So it just seems like as of right now, like you said, the Malcolm situation is kind of
15:49 the most volatile one of the Celtics right now.
15:51 But we don't know about that, right?
15:53 Like, obviously, the vibes could be terrible at the end of training camp, and it could
15:56 be very obvious that a trade is needed.
15:58 But that's not said still, like training camp starts next weekend, and then you have, you
16:03 know, we're a little less than a month away from the start of the season.
16:06 So at this point, though, I think you kind of just look at your options and see how the
16:10 roster battle takes out, maybe a Lamar Stevens or somebody surprises you a little bit.
16:15 I think you can kind of go from there.
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16:46 That's OddsR.com/Celtics.
16:47 Yeah, it'll be some fun end of roster battles during camp here that we'll get to be watching
16:54 in a couple of weeks.
16:56 And the other one thing with Drew too, I think it was worth us discussing, is like, he's
17:01 got one year left in his deal.
17:03 He's going to opt out, he's going to want a new big contract at age 34.
17:09 And the Celtics, A, may not be able to afford that, and B, may not want to pay that regardless.
17:15 And so are you willing to just give up that much for one year of a guy?
17:23 Which a case can be made for that, be like, okay, push in all your chips.
17:26 Yeah, like make a team that is impossible to stop and then deal with the ramifications
17:31 later.
17:32 But then if that doesn't work, then you're in a really, really rough spot next summer.
17:39 Yeah, I don't know, B-Rob.
17:41 I kind of thought, maybe not like, obviously Drew Traver would be all in, but it felt kind
17:46 of like last year for the Celtics, they had a kind of like a very ideal situation in terms
17:51 of like pushing all your chips in, especially with the new CBA and everything.
17:54 Like they had a guy like Malcolm Browderman being a sixth man, right?
17:57 Like you had a Derek White who wasn't even necessarily, like he played all 82 games,
18:01 but there were times when he wasn't even necessarily a starter.
18:03 Like that kind of felt to me like the team where you didn't necessarily go all in because
18:07 you're not dealing with like picks and like kind of paying it forward and everything like
18:11 that.
18:12 But that felt like a all in situation in the sense of this, it wasn't going to get to be
18:17 a much better situation, it felt like.
18:19 And so I think that with, it just seems like a Drew holiday trade though, you would have
18:25 to pay it forward a few years later.
18:27 It's kind of like the NFL where you just kind of kick the can down the road with a salary
18:30 cap and restructure salaries and everything.
18:32 Like the Celtics don't necessarily have that going forward.
18:35 So I don't think they necessarily need to do that just because I think the number one
18:38 thing with the Celtics right now is that this feels sustainable in the sense of like you
18:42 have Jalen locked up, you're going to lock up Jason.
18:44 And obviously you're going to have to be savvy.
18:46 You're going to have to hope like a Jordan Walsh or someone hits eventually down the
18:50 lines and cheap production, but this still feels sustainable.
18:53 Whereas with the Bucs, right?
18:54 Like Damon's 33.
18:55 Yeah, sure.
18:56 Giannis might not necessarily leave anytime soon, but Brooke Lopez is getting up there
19:00 in age.
19:01 Chris Middleton is getting up there in age.
19:02 Like it doesn't change the fact that they have a very stagnant roster as a Celtics,
19:06 you know, they're, they're in a good spot in terms of like the front office has done
19:08 it.
19:09 It's done a, in my opinion, a great job in terms of keeping this as I said, as a sustainable
19:13 product as of now.
19:14 No, I think that's a really good point.
19:16 Like, like this for the Bucs, this could be a one or two year spell.
19:18 Like if things don't like, this doesn't work there, like they could just blow it up next
19:22 summer and be like, let's take, if Giannis is going to leave, like, let's, let's get
19:27 all we can from now who wants Dame, like Brooke Lopez, you're old too.
19:31 Like, we don't want to pay you all that money.
19:33 Let's like, you know, that's, again, that's extreme.
19:37 Like I don't expect that to happen.
19:38 Like they could obviously win all, but like it, there's, there is a very real downside
19:43 Milwaukee here and there again, they, they kind of foresaw that probably coming anyway.
19:47 So they're trying to make this trade to, you know, fight back against it and at least give,
19:52 you know, something for Giannis to hold onto.
19:55 Maybe they, even if they start out strong, like, Hey Giannis, this looks pretty good.
19:58 You want to sign this thing now?
19:59 Like, what do you think?
20:02 But it seems like he's probably just going to keep the pressure on and knows that all
20:06 these guys are in their thirties.
20:07 And like, even like Chris Milton, like what is he looking like anywhere close to himself
20:12 last year.
20:13 So he's probably like the biggest X factor and all this stuff.
20:15 He gets to be the third option, but like, if he's not right, then it's like, okay,
20:19 like that's defendable.
20:20 Yeah.
20:21 I mean, at the end of the day, like we, the big thing with Dame, I thought with trading
20:27 him was like, he could make $63 million in 2026, 27 at age 36.
20:32 Right.
20:33 Like we, Dame is awesome.
20:34 I've been a Dame, you know, I've enjoyed watching Dame for a long time and I got a few friends
20:39 being like, Oh, steam fan.
20:40 And I'm like, yeah, man, it's great.
20:41 But look, like he's getting up there in age.
20:42 You just don't know what the books are going to look like.
20:43 And conversely, you don't know what Giannis is going to look like.
20:44 I feel like that's the kind of the biggest question mark right now.
20:45 So, but you know, we'll see, I'm excited for the season.
20:52 There'll be Rabbi, you know, we've got the Celtics week ahead, media availability and
20:58 everything.
20:59 And I'm sure we're going to get, get into, you know, kind of the, the thick of it very
21:02 soon here, enjoying the last few days of the off season.
21:06 But it should be fun, man.
21:07 I'm really looking forward to it.
21:08 It really should.
21:09 It's plenty of meat on the bone to start this training camp here next week.
21:13 And where it's all day situation or just camp itself, plenty of storylines here.
21:17 We'll be on top of it all at mass life between switching myself, starting on media day on
21:24 Monday.
21:25 So check us out there, check out on Twitter or X, if you will, at Suici, S-O-U-I-C-H-I-T-U-R-A-T-A.
21:31 If you're not already, you should be.
21:34 And yeah, that's it guys.
21:35 We'll obviously be on top of these roster moves in the weeks to come in the days to
21:40 come here.
21:41 If anything breaks, we'll be on it.
21:42 And in the meantime, we'll see you guys at camp next week.
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