2021 NBA Free Agency Winners & Losers: Bet Picks & Predictions for Next Season

Last Updated: Aug 30, 2021

The NBA’s annual free agency period is in full swing, and there’s already been plenty of activity around the league. As of this writing, all but two teams have struck deals, with some making as many as nine roster moves.

Most of the noise came shortly after gates opened Monday evening, though announcements have continued to trickle in throughout the week. And while there’s been significant movement among some of the better players in the league, several up-and-coming stars have reportedly agreed to long-term contracts to stay with their current teams. This includes Trae Young, Shai Gilgeous-Alexander, and Luka Dončić, who are among the future faces of the NBA.

However, not every deal is a great one. Just as there are steals, there are guys who have been massively overpaid relative to their performance, age, and role. Below, we’ll look to sort out some of these deals and evaluate which teams and players fall on the two ends of the spectrum.

Of course, the free agency period remains an ongoing process, so while there could be other teams and players who wind up in the winners and losers conversation, the ones listed below have done plenty to set themselves apart from the rest — for better or for worse.

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2021 NBA Free Agency Winners & Losers: Evaluating Best & Worst Deals

Winners: Miami Heat

The Miami Heat set themselves apart from the crowd early in free agency, moving quickly to add veteran point guard Kyle Lowry. The 35-year-old was a six-time All-Star with the Toronto Raptors and helped secure the franchise’s lone NBA title in 2019, solidifying his standing as one of the greatest players in Toronto’s short history. A terrific two-way player, Lowry will provide a nice boost to Miami’s lackluster offense and improve upon what was already an impressive defense.

Miami also acquired forwards P.J. Tucker and Markieff Morris, who bring physicality and championship experience to the roster. Tucker won the 2021 NBA Finals with the Milwaukee Bucks, while Morris played a key role off the bench for the title-winning Los Angeles Lakers in 2020.

The Heat also returned sharpshooter Duncan Robinson, two-way guard Victor Oladipo, and center Dewayne Dedmon and are expected to come to terms with star Jimmy Butler on a maximum contract extension, setting themselves up to compete for an NBA title for years to come.

Winners: Chicago Bulls

It’s been four years since the Chicago Bulls last appeared in a playoff game, but that’s likely to change in 2022. Since free agency opened earlier this week, the Bulls have added versatile guard Lonzo Ball and a former All-Star in DeMar DeRozan to pair with stars Zach LaVine and Nikola Vučević, giving them a solid core to work with for the foreseeable future.

The offensive upside here is obvious. All four players are capable scorers and passers, and although DeRozan is essentially a non-factor from beyond the arc, he’s one of the more efficient mid-range shooters in the NBA. The additions also allow Coby White to slide into a role as Chicago’s sixth man, where he could truly shine as a scoring guard.

The Bulls also signed Alex Caruso to a four-year deal, giving them an athletic 3-and-D combo guard who can provide a spark off the bench alongside White.

Chicago may not be in position to contend for a title just yet, but they’ll be one of the more entertaining teams in the league next season and will be worth keeping an eye on.

Winners: Old Guys

It’s been one heck of a summer for 35-and-ups looking to sneak one last NBA title onto their resumes.

The Los Angeles Lakers have opened the doors for virtually every aging veteran in the league, signing Carmelo Anthony (37), Trevor Ariza (36), and Dwight Howard (35) to one-year deals. Wayne Ellington (33) and Kent Bazemore (32) will also be taking advantage of the early bird specials in Los Angeles.

Elsewhere, Taj Gibson (36), Rudy Gay (35), and Jeff Green (35) have all signed contracts to remain in the NBA for another year or two.

Of course, some of these guys are more playable than others. Chris Paul (36) and Kyle Lowry (35) each got paid the big bucks by their respective teams, but they’ve aged relatively gracefully. The same could be said of Mike Conley (33), who signed a three-year deal to return to the Utah Jazz.

No matter the case, it’s clear that age is viewed only as a number by some front offices around the league.

Winner: Kemba Walker

A month ago, it looked as though Kemba Walker would spend the upcoming season with the Oklahoma City Thunder, wasting a year of his prime with a team looking to compete for nothing more than a top pick in the 2022 NBA Draft.

Instead, the four-time All-Star is packing his bags for the Big Apple after agreeing to a buyout with the Thunder, allowing him the opportunity to play a key role for his hometown New York Knicks as they look to secure a second consecutive playoff berth.

Walker should immediately step into a starting role with the Knicks, who were in desperate need of improved guard play. New York ranked among the worst teams in the league last season in points per game and offensive rating, so Walker — a savvy, score-first guard — should be a natural fit. Of course, health has been an issue for him as of late, as the 31-year-old has missed 45 games due to injury over the past two seasons. There’s certainly some risk involved here for the Knicks.

Nonetheless, it’s safe to say Walker’s situation has improved since he was traded by the Boston Celtics in June.

Kemba Walker, PG, New York Knicks

Oct 26, 2019; New York, NY, USA; Boston Celtics guard Kemba Walker (8) dribbles up court during the second half against the New York Knicks at Madison Square Garden. Mandatory Credit: Vincent Carchietta-USA TODAY Sports

Losers: New Orleans Pelicans

For a while there, the New Orleans Pelicans were expected to be big players in free agency. Rumors circulated about the franchise’s ability to nab Kyle Lowry after moving off the contracts of Steven Adams and Eric Bledsoe, who seemingly would have paired nicely with stars Zion Williamson and Brandon Ingram.

Instead, Lowry signed with the Miami Heat, and the Pelicans sent Lonzo Ball to the Chicago Bulls via sign-and-trade. In return, New Orleans received Tomáš Satoransky, Garrett Temple, and a second-round pick. The Pelicans also acquired guard Devonte’ Graham in a separate deal with the Charlotte Hornets, parting with a lottery-protected first-round pick in the process.

Graham is quite good — probably not better than Ball — but he’ll bring consistent three-point shooting to a Pelicans team that posted the fifth-worst three-point percentage in 2020-21. However, considering the lofty goals New Orleans set for this offseason and the price they paid to put themselves in position to acquire a big-name free agent, it’s hard to be impressed with the moves they made.

Losers: Milwaukee Bucks

After winning their first championship in 50 years last month, the Milwaukee Bucks didn’t need to do much in free agency to improve. The only task at hand, really, was to retain some of the role players who helped make their memorable title run possible.

Milwaukee got off to a good start by re-signing fan-favorite Bobby Portis on a team-friendly two-year deal worth $9 million, but things have gotten slightly downhill since.

Bryn Forbes and P.J. Tucker — each of whom saw considerable playing time throughout the postseason — signed elsewhere. Forbes, who shot a career-high 45.2 percent from three this season, agreed to return to the San Antonio Spurs. Tucker, an enforcer on the defensive end of the floor, struck a deal with the Miami Heat.

Milwaukee still has a chance to turn things around, but for now, it’s hard to get too excited about their offseason moves.

Loser: Dennis Schröder

It’s been a nightmare offseason for Dennis Schröder. After reportedly declining a four-year contract extension worth $84 million to stay with the Los Angeles Lakers earlier this season, the 27-year-old combo guard has found himself without a suitor several days into free agency.

The Lakers have made it abundantly clear that he’s no longer needed, trading for Russell Westbrook and signing Kendrick Nunn and Malik Monk to fill out their guard rotation.

Other teams have made it clear that they aren’t interested in shelling out big money to bring him in, either. Few teams, if any, can afford to give Schröder the type of payday he was looking for when he declined the Lakers’ offer, and it’s hard to imagine there’s a team out there that would be willing to do so if it could.

Schröder could still find himself in a good situation relatively soon, as he’s still an above-average player. After all, he was a finalist for the Sixth Man of the Year award in 2019-20, and he averaged 15.4 points and 5.8 assists per game for the Lakers in 2021. With that said, to say he miscalculated his value would be an understatement.


Garrett Chorpenning

Garrett Chorpenning is the Lead NBA Editor for The Game Day. His previous work includes covering the LA Clippers for Sports Illustrated and FanSided. He graduated from Ball State University in 2021.

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