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Bold NBA Trades That Need to Happen

Grant HughesApr 27, 2023

Even if we spend virtually all season (and offseason) focusing on transactions, most NBA trades don't materialize until they absolutely have to. The deadline and the July flip-over of each new league year spur action, but teams generally hold off on big deals because the alternative, standing pat, is so much safer.

Sometimes, though, a little boldness is necessary.

All the trades here are designed to draw double takes. They involve big names, tough decisions and high stakes.

These are the deals that need to happen, even if the teams involved may not be quite ready to admit it.

Damian Lillard Finally Moves On

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PORTLAND, OR - NOVEMBER 17: Damian Lillard #0 of the Portland Trail Blazers looks on before the game against the Brooklyn Nets on November 17, 2022 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2022 NBAE (Photo by Sam Forencich/NBAE via Getty Images)
PORTLAND, OR - NOVEMBER 17: Damian Lillard #0 of the Portland Trail Blazers looks on before the game against the Brooklyn Nets on November 17, 2022 at the Moda Center Arena in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2022 NBAE (Photo by Sam Forencich/NBAE via Getty Images)

The Trade: Brooklyn Nets acquire Damian Lillard from the Portland Trail Blazers for Nic Claxton, Royce O'Neale, Spencer Dinwiddie, 2025 first-round pick (via Phoenix Suns), 2027 first-round pick (via Philadelphia 76ers), 2028 first-round pick (via Phoenix Suns), 2029 first-round pick (via Dallas Mavericks)


The Brooklyn Nets' experience with Kyrie Irving, James Harden and Kevin Durant shouldn't put them off chasing stars entirely, but it should have taught them to prioritize reliability in their pursuits. That makes Damian Lillard, so far a one-franchise player whose loyalty borders on superhuman, an intriguing change of pace.

Reports indicate the Nets at least have their antennae up on Dame.

"If Lillard and Portland decide a parting of ways is best for both sides, multiple NBA executives believe the Nets could be a suitor for the All-Star guard," per Michael Scotto of Hoopshype.

If the Blazers finally rebuild, they could do a lot worse than getting one of the league's best young bigs in Claxton, plus a pick haul that allows them to bet against the distant futures of three teams—Phoenix, Dallas and Philadelphia—with aging, potentially disgruntled and/or injury-hit stars.

Dinwiddie and O'Neale are starters on expiring deals the Blazers could flip for more draft equity, a key for a franchise that hasn't attracted free agents and must build through the lottery and trades.

The Nets should consider offering another pick or Dorian Finney-Smith instead of Claxton, whose defensive mobility and shot-blocking make him an ideal Lillard complement—the kind of difference-making center he's never really had in Portland.

Ben Simmons is another candidate to move (more on that later), but if the Nets used him as the main matching salary, their pick outlay would get prohibitively larger. The 2016 No. 1 selection may be at a point where teams would want assets attached to take on his salary.

It's never been wise to expect a Lillard move, and we've got more than a decade of evidence saying he prefers life in Portland. But Dame might enjoy a change of scenery in a big market with emerging star Mikal Bridges, a player for whom he's expressed public admiration.

O.G. Anunoby as a Lillard Appeasement Plan

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PHILADELPHIA, PA - MARCH 31: OG Anunoby #3 of the Toronto Raptors dribbles the ball during the game against the Philadelphia 76ers on March 31, 2023 at the Wells Fargo Center in Philadelphia, Pennsylvania NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by David Dow/NBAE via Getty Images)
PHILADELPHIA, PA - MARCH 31: OG Anunoby #3 of the Toronto Raptors dribbles the ball during the game against the Philadelphia 76ers on March 31, 2023 at the Wells Fargo Center in Philadelphia, Pennsylvania NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by David Dow/NBAE via Getty Images)

The Trade: Portland Trail Blazers acquire O.G. Anunoby and Precious Achiuwa for Anfernee Simons and either a 2023 first-round pick or a 2026 first-round pick (top-four protected)


The Blazers have an alternative to the teardown we just suggested in the Dame-to-Nets section: They can take a major swing to improve the roster in the short term, hopefully giving Lillard no reason to offer the ultimatum he at least hinted could be coming when he told ESPN's Stephen A. Smith:

"It ain't a threat. I ain't gonna say I'm putting them on the clock. I'm just saying if those things can't be done—if we can't do something significant like that—then we won't have a chance to compete on that level. And then, not only will I have a decision to make, but I think the organization will, too. Because at that point, it's like, 'Are you gonna go young, or are we gonna get something done?'

Anunoby is among the most fearsome, versatile defenders in the game. A burly forward with long arms, the heft to guard bigs and the No. 3 defensive estimated plus/minus in the entire league, he'd surely get Portland out of the bottom five in defensive efficiency, where it's resided every year since 2019-20.

Capable of checking centers, Anunoby also held his assignments to the lowest points per play of any wing who covered at least 100 isolation possessions.

Achiuwa is a project, but he'd address the Blazers' lack of athleticism at the 5.

From Toronto's perspective, this is mainly about avoiding the cost of Anunoby's next contract, as he'll likely hit free agency in 2024 (player option for 2024-25), and adding a young playmaking guard in Simons, who could help get its half-court offense up to speed. The allure of either draft-pick option listed above should be more than enough to get the deal done from the Raptors' end.

The Wizards and Hawks Swap Problems

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Trae Young and Bradley Beal
Trae Young and Bradley Beal

The Trade: Atlanta Hawks acquire Bradley Beal, Deni Avdija and a 2023 first-round pick* from the Washington Wizards for Trae Young


The Washington Wizards will have a new lead executive in place of the deposed Tommy Sheppard, and that person should be more amenable to getting rid of the quarter-billion dollar deal Beal signed just last summer. And for a franchise that has gotten precisely zero from the point guard spot since John Wall was an All-Star in 2017-18, the target for a return package is clear.

Young's value may be near its lowest point. Two years after making the Eastern Conference Finals and delighting in the villainous role his brash style earned him, the 24-year-old two-time All-Star has been more notable lately for clashes with coaches, dubious leadership and a refusal to move off the ball.

Beal's enormous deal and average of 30 missed games over the last four years make him one of the league's toughest players to trade. That's why the Wizards have to include a promising defensive forward in Avdija and that 2023 first-rounder, even for an out-of-favor star like Young.

Of course, if he keeps hitting playoff game-winners to stave off elimination, Young's price could climb.

The Hawks could go forward with Beal alongside Dejounte Murray in the backcourt and hope that the talent on hand would jell more effectively with Young out of the picture and more touches to go around. Meanwhile, Washington would add the primary shot creator it has long lacked while getting out from under a contract that would have paid Beal $57 million in 2026-27, his age-33 season.

*Because the Wizards can't trade first-rounders in consecutive years, they technically have to make their first-round selection in 2023 and trade that player as part of the package for Young.

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Dallas Shoves In Its Remaining Chips

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Alex Caruso
Alex Caruso

The Trades:

  • Dallas Mavericks acquire Alex Caruso from the Chicago Bulls for Reggie Bullock and a 2023 first-round pick
  • Dallas Mavericks acquire Jonathan Isaac from the Orlando Magic for Davis Bertans and a 2027 first-round pick (lottery protected)

The way forward for Dallas is clear. It has no choice but to retain impending free agent Kyrie Irving on a new deal and move anything that's not nailed down to bring back enough defensive punch to keep Luka Dončić from becoming the next superstar to demand a trade.

But when you're perilously short on movable assets, surrendering the biggest ones counts as bold. That's exactly what the Mavs are prepared to do, per Marc Stein:

"Retaining this June's pick would provide a crucial potential path to a quality player for a club low on trade chips or the salary-cap flexibility to make significant changes around Doncic and Irving. Sources say that the Mavericks plan to explore trade prospects with the pick if they retain it to potentially seek more win-now talent."

Here, we've got Dallas swinging a pair of deals to net Alex Caruso and Jonathan Isaac. The former is on the shortlist of the league's best backcourt on-ball pests, while the latter's ascent to perennial All-Defensive team status has been interrupted by constant injury.

The Caruso deal hinges on Dallas keeping its first-rounder, which won't be the case if it falls outside the top 10 on May 16 when the lottery is held. The Bulls would also have to embrace a more future-focused mentality to consider giving up such a valuable vet for a late lottery pick, although Bullock and his career 38.4 percent knockdown rate from deep could help a win-now version of the Bulls improve a dead-last ranking in three-point attempts.

Isaac may never be able to stay healthy, but his ceiling remains high. He's exactly the kind of dynamic havoc-wreaker the Mavs defense lacks. When fit, he can plug holes all over the floor and disrupt opposing offenses with his length.

The elite block and steal rates that defined Isaac's career persisted in his cameo this season before an abdominal injury shelved him again. Bertans' onerous deal will pay him $33 million over the next two years (player option for 2024-25), but he can still stripe it from deep. With Isaac having played just 11 games since 2020, the Magic might prefer someone with better odds of contributing.

The Mavs would certainly prefer splashier moves to keep Dončić happy, but the upside of adding one excellent backcourt defender and a switchable center who might be even more impactful if healthy may be the best they can do.

Ben Simmons Gets a Fresh Start

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NEW YORK, NEW YORK - FEBRUARY 11: (NEW YORK DAILIES OUT)  Ben Simmons #10 of the Brooklyn Nets in action against the Philadelphia 76ers at Barclays Center on February 11, 2023 in New York City. The 76ers defeated the Nets 101-98. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Jim McIsaac/Getty Images)
NEW YORK, NEW YORK - FEBRUARY 11: (NEW YORK DAILIES OUT) Ben Simmons #10 of the Brooklyn Nets in action against the Philadelphia 76ers at Barclays Center on February 11, 2023 in New York City. The 76ers defeated the Nets 101-98. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Jim McIsaac/Getty Images)

The Trade: San Antonio Spurs acquire Ben Simmons from the Brooklyn Nets for Doug McDermott and a 2023 first-round pick (via Phoenix Suns)


It seems clear Ben Simmons would benefit from a fresh start in a low-stakes environment, which makes the stable, rebuilding Spurs the ideal destination for his hypothetical career resuscitation. Gauging his value is the tricky part.

Simmons missed all of 2021-22 and was a shell of himself in 42 games this past season for the Nets. His refusal to shoot jumpers and reluctance to seek contact in the lane drove his scoring average down to a career-worst 6.9 points per game. Health may have been a factor.

The good news, per the New York Post's Brian Lewis, is that Simmons is unlikely to need a second back surgery. It's also possible his poor play was attributable to what experts said would be an 18-month recovery timeline following a microdiscectomy performed in May 2022.

San Antonio's hoard of cap space means it can onboard Simmons' deal without issue. As long as the Spurs believe there's enough upside to justify giving up a quality shooter in McDermott and a late first-rounder from the Suns, they can handle the two years and $78.2 million left on Simmons' contract.

Again, gauging Simmons' value is tough. If the Spurs demanded a first-rounder in exchange for all the cap relief they'd be giving the Nets, it wouldn't be out of bounds. If Brooklyn determined Simmons' worth was too low to trade him at all, and that it might be better to wait and see if improved health opens up the market at the 2024 deadline, that might also be sensible.

Simmons, though, could use a clean slate. The Spurs can provide one.


Stats courtesy of NBA.com, Basketball Reference, Cleaning the Glass and Dunks & Threes. Salary info via Spotrac.

Grant Hughes covers the NBA for Bleacher Report. Follow him on Twitter (@gt_hughes), and subscribe to the Hardwood Knocks podcast, where he appears with Bleacher Report's Dan Favale.

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