Which 2021 NBA Offseason Moves Will Look the Worst in 3 Years?

Zach Buckley@@ZachBuckleyNBANational NBA Featured ColumnistAugust 30, 2021

Which 2021 NBA Offseason Moves Will Look the Worst in 3 Years?

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    Knee-jerk reactions are part of the NBA offseason experience.

    That's why each summer of drafting, dealing and doling out big contracts is immediately met by lists of offseason winners and losers.

    That analysis serves a purpose, as player and team track records typically provide enough information to formulate an educated guess on how these arrangements will go. However, as these are often long-term commitments, the true impact of them can only be revealed over time.

    Unless, of course, you have access to a trusty crystal ball, which luckily we do.

    We'll lean on that spherical soothsayer and our own forecasting to determine which 2021 offseason moves will look the most regrettable three years from now.

Houston Giving Daniel Theis a Four-Year Deal

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    Win-now shoppers should have had interest in Daniel Theis.

    He bangs around the basket on both ends of the floor, sets solid screens and doesn't torpedo his value by stepping away from the rim. As a 29-year-old glue guy, he would've been an easy fit in a veteran-heavy locker room loading up for a championship run.

    So, how in the heck did he end up on the Houston Rockets?

    They might claim to be seeking a fast track toward competitiveness, but their other offseason moves communicate a better grasp on their post-James Harden reality. They spent four first-round picks on four teenagers. Regardless of how you feel about the prospects—Jalen Green, Alperen Sengun, Usman Garuba and Josh Christopher—you can at least admit they probably won't contribute to winning sooner than later.

    If Houston is taking the long view with its major moves, why lock Theis up on a four-year, $35.6 million contract? Sure, the final season is a team option, but will he earn his keep before that? Even fashioning him as a future trade chip is tricky because modern teams are reluctant to pay most centers, so they probably won't want to commit $8 million-plus of their cap room to a non-star big man.

    Looking into the future, Theis' role will ideally decrease with time, as that will mean players like Sengun and Christian Wood have commanded more minutes. That's not exactly going to help Theis' marketability as a trade chip.

Portland Guaranteeing All Five Years of Norman Powell's Contract

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    Norman Powell had leverage on the Portland Trail Blazers, and everyone knew it.

    They tipped their hand about their future plans for him by acquiring him at the deadline during his contract year and doing so at the expense of promising, young swingman Gary Trent Jr. The Blazers were backed into a corner with Powell even before Damian Lillard pressured their front office to put the roster in the best shape possible.

    A bloated salary seemed highly likely, then, and a bloated salary is what he received. The career 10.4-points-per-game supplier will cost $15.5 million next season and more each of the ensuing four years. That's a ton for a scoring specialist who frankly didn't do a lot of scoring during his first four NBA seasons.

    However, it's the longevity of this contract that looms most ominously. All five years are fully guaranteed, and he'll enter his 30s before the deal is even halfway over.

    Perhaps Portland felt it had no other choice with Lillard's frustration, but who's to say he'll stick around for all—or even most—of Powell's pact? When asked on a recent Instragam Live why he's leaving Portland, Lillard could only offer, "I'm not leaving PDX—not right now at least."

    It's one thing to overpay Powell to play a support role alongside a superstar. It's quite another to burden the books with this deal should Lillard force his way out and send Portland spiraling into a rebuild.

    It feels increasingly likely Lillard will split from the Blazers at some point in the next three years, but Powell and his massive deal will almost certainly still be around unless Portland sacrifices assets to incentivize someone to take him off its hands.

Cleveland Giving Jarrett Allen $100 Million

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    In theory, a rebuilding team locking up an ascending 23-year-old on a five-year, $100 million deal sounds defensible, if not outright genius. In this situation, though, the logic is hard to follow behind the Cleveland Cavaliers' commitment to Jarrett Allen, and the passage of time might only work to highlight the issues.

    For starters, Allen plays a role that rarely, if ever, warrants that kind of contract in the modern NBA. He's an active, athletic rim-runner and rim protector. While almost every team needs that, they're readily available and often pretty cheap. JaVale McGee checks the same boxes, has proved he can contribute to a champion (three times) and still managed to find only a one-year, $5 million deal from the Phoenix Suns.

    Now, Allen is a decade younger than McGee and already more reliable, so it's not an apples-to-apples comparison. The bigger point, though, is that most modern centers who don't space the floor aren't worth nearly that kind of coin.

    Zeroing in on Cleveland specifically, the fit between Allen and incoming rookie—and No. 3 pick—Evan Mobley looks clunky at best. Even if they have the mobility to co-exist defensively, neither has flashed the shooting range needed for the twin-towers model to work offensively. Not to mention, the frontcourt is crowded around them with Kevin Love still on the payroll and Lauri Markkanen reportedly headed to town on a $67 million deal, per ESPN's Adrian Wojnarowski.

    At some point in the next three years, it seems reasonable to assume Cleveland will discover Mobley is best utilized at center. What happens at that point with Allen? Benching a $20 million player is suboptimal, and trading Allen might require serious concessions from the Cavs given his skill set and salary.

    It's a confusing arrangement right now and could be downright baffling in a few years.

Toronto Giving Gary Trent Jr. a Player Option

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    When attaching contract values to players, there's a baseline expectation from NBA teams that the players will perform up to their pay rate. The real wish, though, is for the player to outperform his salary and create a surplus value.

    There's basically zero chance for that to happen with the three-year, $51.8 million deal the Toronto Raptors gave Gary Trent Jr.

    He'll have a hard enough time living up to that salary. He shines as a three-point shooter (career 39.3 percent) but doesn't really stand out in any other area. He is solid defensively, but his size (6'5", 209 lbs) limits what he can do against bigger wings. He doesn't create shots for his teammates (career 1.1 assists per game) and struggles to generate them for himself.

    Maybe his three-and-D skills are sharp enough to warrant the salary, but that would actually create a separate issue, as he can shake out of this deal by declining his player option for 2023-24. The option creates a problem for the Raptors that time can't solve.

    "If he underperforms, he'll stay the extra year on an undesirable number; if he's good, he'll leave or force Toronto to pay him more," The Athletic's John Hollinger wrote. "And if he somehow does outperform, the fact his option is in the third year also makes it impossible to extend the deal before he hits free agency again."

    Securing young talent might make sense for a team in Toronto's position, but not like this.

Chicago's Sign-and-Trade for DeMar DeRozan

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    Virtually every part of the Chicago Bulls' sign-and-trade for DeMar DeRozan is a mind-boggler.

    Let's start with the contract, which came in at three years, $85 million and is fully guaranteed. Who was Chicago bidding against to feel the need to go this high and for this long at the negotiating table? The Oklahoma City Thunder were the only team with major money left, and that obviously wasn't a fit. DeRozan also didn't make sense for a San Antonio Spurs squad finally seeing the merits of a youth movement.

    The Bulls should've had leveraged, but if they did, they exercised exactly none of it.

    Now for the fit: How will a team headlined by DeRozan, Zach LaVine and Nikola Vucevic ever get enough stops to win anything of substance? It's like the Bulls' brass decided to follow the Brooklyn Nets' model for roster construction, only they forgot to get one player—let alone three—on the level of Kevin Durant, James Harden and Kyrie Irving.

    DeRozan works best with the ball in his hands. So does LaVine. Vucevic can't get lost in the shuffle, and Patrick Williams needs all the developmental touches he can get. How is this all going to work?

    "Lot of people I see criticizing, talking about 'fit this, fit that' have probably never even played basketball," DeRozan told reporters. "For me, if everybody (is) on the same page mentality and wants to win, it don't matter about a 'fit,' because it's all gonna come together how it need to come together and make it work."

    That might be the right mentality for DeRozan to have, but saying that it's going to work doesn't actually explain how it will. Chicago basically put all of its chips behind an offense that should be good but quite possibly won't be great. How far can a team follow that formula? Probably nowhere near championship contention.

    DeRozan won't get better with age (his decline could start at any time), and the 30-year-old Vucevic could be starting his descent, too. Is that enough reason for LaVine to look elsewhere in free agency next summer? If he signs a massive extension before then, will the Bulls have just locked into a core that can't compete for a title?

    The questions are clear and concerning right now, and it's hard to see what could possibly silence them over the next three years.


    Stats courtesy of NBA.com and Basketball Reference unless otherwise noted. Contract information via Spotrac.

    Zach Buckley covers the NBA for Bleacher Report. Follow him on Twitter, @ZachBuckleyNBA.


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