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Doubting Thomas: could the Celtics trade Isaiah Thomas?

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We've heard rumors about moving Marcus Smart for Jahlil Okafor or packaging Jae Crowder for Jimmy Butler, but there has never really been a mention of moving Boston's best player, Isaiah Thomas.

David Butler II-USA TODAY Sports

It seems unfathomable for a rebuilding team like the Celtics to trade their best player, who's currently on a bargain deal and only 27. For Boston, though, dealing Isaiah Thomas could be their chance to maximize their assets for a championship run in the future. Bill Sy and Lachlan Marr debate.

BILL: This is my biggest worry heading into what is arguably the most consequential summer for Danny Ainge: what if nothing happens? If he can't make a draft night trade with the #3 pick, that could hurt his chances in free agency two weeks later. If that happens, we could be looking at a long(er) rebuild with Isaiah Thomas as our best asset.

LACHLAN: I completely agree that this will be a consequential summer for Ainge. But to me the rebuilding schedule has been hastened exactly because of Isaiah's play, which is why everyone is so eager for a big offseason. All the talk at the moment is rightly about how the Celtics are looking for their second star, having already found their first in Isaiah. I'd be curious to know what type of deal you think would be worth trading IT for. Because in my mind, any trade involving IT would be a case of one step forward, two steps back.

BILL: If Ainge strikes out this summer, the team could be in full rebuild mode with IT as the elder statesman. Thomas is 27 and heading into his prime, but does it make more sense to bring in guys that fit into a younger age profile? If Thomas could fetch another lottery pick—say from Minnesota, New Orleans, or Sacramento—Ainge could draft potentially three or four players this summer to develop with Marcus Smart, Kelly Olynyk, and the rest of the roster on rookie contracts.

LACHLAN: I feel like trading away IT for some draft picks, even high ones, would the biggest way in which Ainge could strike out this summer. Every time a team has traded away IT in the past they have ended up on the losing end of that deal. From all accounts Ainge is pursuing his rebuilding goals with the patience of an Irish-Catholic saint. He doesn't seem interested in a deal that will make the team incrementally better by sacrificing what the Celtics have now or mortgaging their future. Trading IT when he's on a good contract and is the team's lone All-Star seems like it would do exactly that. The Celtics already have a young core, and while IT might not be the ideal elder statesman, it would be better to have him around to guide the young players Boston has. Ainge already has plenty of tradeable assets—why not move them?

BILL: Ideally, it would be better to trade picks #16 and #23 to move up in the draft, but I doubt that gets us into the top 10. In the immediate, losing Thomas is a step back, but in two years, you could potentially have a matured Dragan Bender and Jaylen Brown or Kris Dunn in the starting lineup. Maybe Ainge manages to pry away Gorgui Dieng or work out a sign-and-trade with Jared Sullinger for Ryan Anderson. I agree that Ainge had been patient, but he might have to be more patient and plan for years in advance.

LACHLAN: To me that would be too patient and too much of an investment in essentially untested potential. I get the idea that you would have all these young guys on the same development schedule. But all-rookie style teams tend to find themselves in the same position the Celtics are in right now, just further down the track. When building through the draft teams seem to often hit a point after a few years where they have a few good pieces that work but need one or two more to really contend. The biggest danger in that scenario is trading the wrong player and regretting it. I just don't see why the Celtics would do that after lucking into Thomas and accelerating their rebuild all for a chance to be in the same position further down the track. If IT were to be traded, I feel like it would only work if he was being used to bring back a player the Celtics were sure they could build around.

BILL: It's all a gamble, but I think you have to maximize your bet. Part of it is also fit and function. Don't get me wrong: I love Thomas, but the guard position happens to be our deepest. With Smart, Bradley, Hunter, Rozier, and several draft picks on the horizon, it's the one spot we could afford to free up space in.

LACHLAN: True, the Celtics are stacked at the guard position, and there's something to be said for maximising your options. But I still feel like trading Thomas would be a step in the wrong direction. While there's definitely several team needs to address, this type of trade just seems like it would create more problems rather than act as a real solution.

BILL: Trust me. Trading Thomas is one of these potentially hard decisions that I wouldn't want to make as a GM. Thomas has been a model Celtic and understands the opportunity and responsibility representing this franchise. But what if an offer like this comes around? A deal like that could plug two holes without hurting back court depth.

LACHLAN: I like that deal. Minnesota have some great prospects, like LaVine and Dieng, and if we were to snag a draft pick on top of them that would be a coup for the Celtics. Plus it's exactly the type of deal I could see Ainge pursuing. But there's a reason—beyond Thibs wanting to win now—Minnesota would be interested in trading for a player like Butler or, in what I assume is your alternate version of the deal, a player like Thomas. Raw talent is great, but players with proven potential like IT or Butler are even more valuable. A Larry Bird in the hand is worth two in the draft, so to speak.

BILL: For me, so much of Thomas's appeal is that he's such a bargain at ~$6M per year for the next two seasons. The question is, in 2018 after the salary cap has somewhat normalized, would you pay a near 30-year-old Thomas a max deal?

LACHLAN: The fact that Isaiah is on a good contract definitely increases his trade value, but surely it also increases his actual value to the Celtics. With an All-Star player on such a forgiving contract, the Celtics have the extra cash and cap space to pursue the other pieces that could turn them into true contenders. Whether or not Thomas is worth a max contract in two years would depend entirely on the events that transpire over the next two years. If Ainge can find Thomas some decent help then there's every reason to believe Thomas will elevate his play when complimented by the right roster around him.

BILL: That's a good segue to what could be a good fit for Thomas. According to Synergy, IT was a very efficient scorer as a ball handler in pick-and-rolls and a good scorer in isolation, but that's not really Celtics basketball under Brad Stevens. We saw against the Hawks (and the Cavs last postseason) how teams can key in on Thomas and take him out of his game. What kind of player do you think Ainge can add that makes Thomas more effective and vice versa, one that Thomas can bring out the best from?

LACHLAN: Hmmm, it's a fairly open-ended question. There's probably plenty of players who would complement IT well. But I don't think it's a secret that Boston could use some additional frontcourt depth. And if Ainge is able to find a capable big man through trade or free agency, I think we would see Thomas's numbers improve dramatically. If Boston had a more prominent presence in the paint it would help Isaiah and the overall offense considerably.

Not only would having a competent big man would allow IT to create more plays through pick-and-roll manoeuvres but more than that it would create more space for IT to operate in general. Plus teams would be less likely to completely collapse on Thomas when he's driving to the rim if there was another player who was consistently able to score inside the paint.

I think a solid, serviceable center on the roster could benefit Thomas's game a great deal. No need to search for that mythical stretch five; pace and space can be created just as easily by players who are able to fill their standard role well.

BILL: I agree that Thomas would benefit from another All-Star-caliber player—particularly a big man that doesn't occupy the same space on the floor as he does—but my biggest concern is how little he affected the the players around him. This is a generalization, but I think for the most part the Celtics tried to run a lot of action for Thomas to get him into scoring positions rather than Thomas trying to involve his teammates. He's not a prototypical point guard, and we saw in the playoffs that his ability to work off ball had mixed results. To his credit, he nearly averaged a career high in assists, but nobody got better around him.

LACHLAN: I see what you're saying. Numbers-wise Thomas didn't necessarily help improve the other players on the roster. However he certainly contributed to the Celtics' improvement in the one number that truly matters: their win record. And as you stated he worked on the things he could work on, like attempting to become a more pure point guard and increasing his assists.
Even still, I see the logic in trading Thomas in the way that the Celtics could use upgrades up and down their roster. In fact, one could argue that the Celtics need an upgrade at every position not played by Isaiah Thomas, and a deal—like the one you suggested with the T-Wolves—that trades Thomas to add more pieces could help Boston round out their roster and plan for a more balanced future.

However, with all the tradeable assets at their disposal Boston doesn't have to take the step back that trading Thomas would represent. In theory, they could just as easily find some players to help out their lone All-Star.

I think it's fair to say that the Celtics didn't know what they had when they first acquired Thomas. However, now that they do, they can start more consciously making moves to better build a roster that compliments IT's skill set.

BILL: Like I said at the top, Thomas has been a great Celtic ambassador so far. He's put the team on his back and won games, energized the fan base, represented the Celtics at the lottery, and has started recruiting players to come to Boston. I'm not saying he's Paul Pierce, but you have to wonder if he's an Antoine Walker-like asset that could be moved in order to fill those holes. Coming off an All-Star campaign with two years left on his contract, his value is peaking and maybe even peaked.

Unfortunately, unlike the NFL, the draft happens before free agency. Ainge would have to have a good sense of how free agency will turn out before he'd entertain a Thomas trade, but that's just not happening. For Thomas's sake, he's gotta be hoping that Danny deals #3 for another star, and the two of them can help net a big fish in July.

LACHLAN: Yeah, it makes it difficult with the draft being before free agency, but I hardly think the Celtics are or will end up in a situation where they've put all their eggs in one basket.

Boston has accumulated assets, built up cap room, and already has some young talent. Trading Thomas is only one among many options available to Ainge and the Celtics organisation this offseason, and it is probably the least desirable option available.

Maybe his value from a trade perspective is close to peaking or already has peaked, but do you believe Thomas has peaked as a player?

BILL: To some extent, yes. Individually, he could become a better defender, develop more of a mid-range game, and generally be more consistent, but Thomas's next progression is dependent on his teammates. He'll be more effective and efficient if he has to do less. And there's the rub. Ainge is going to have to give to get, and if it's not IT4, it'll be somebody else that we can't stand to lose like Crowder or Smart.

LACHLAN: Ainge has found gold on the trade market before, and he's likely looking to do it again. A blockbuster deal that trades away Thomas could help set up the Celtics for a bright future, or it could leave them regretting letting go of the little guy with so much love and passion for the game who plays like he's ten feet tall. While IT is sure to have a high trade value, I still think he's more valuable to the Celtics on the court than on the market.

BILL: Well, I know I'm a prisoner of the moment, and right now, it's all about the draft. Whether it's DraftExpress having Marquese Chriss going to the Celtics at #3, or the allure of the unknown in Dragan Bender, or Ainge touting Jaylen Brown's workout at Waltham, I'm admittedly excited about a bunch of players in this draft class. But I think you're right: If there's a deal to be made that helps the Celtics in the future, Danny has to make that deal—even if it means parting with the team's current best player. With Ainge and Stevens extended for the foreseeable future, it wouldn't be too surprising for them to take a step back to take two steps forward.