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The Most Stacked Free Agency In NBA History: LeBron James, Kawhi Leonard, Giannis Antetokounmpo

The Most Stacked Free Agency In NBA History: LeBron James, Kawhi Leonard, Giannis Antetokounmpo

With the weirdness of the 2019-20 NBA season done with and LeBron James holding his fourth championship ring, attention has shifted to the offseason. Trade rumors around superstars like Chris Paul and Giannis Antetokounmpo are rampant, and speculation abounds about how the league’s balance will shift with the Nets and the Warriors both having Finals potential next season.

One thing that this offseason lacks, however, when compared to 2019, is a significant collection of star free agents. Last year was particularly dramatic with Kawhi Leonard, Kyrie Irving, KD, and more all on the market, but 2021’s offseason could be an even crazier time for free agency signings and NBA power shifts. A year from now, these twenty players could all be up for grabs.

20. Spencer Dinwiddie – Player Option

Credit: Getty Images

Credit: Getty Images

Spencer Dinwiddie’s future in Brooklyn largely depends on what the Nets actually look like next season. With Kevin Durant finally back from his year-long Achilles injury, Kyrie (hopefully) healthy for the whole season, and Steve Nash taking a wildcard head coaching role, Brooklyn could be set to tear through the East. On the other hand, KD could return at significantly reduced efficiency, Kyrie’s legs could betray him again, and Nash could flop. We just don’t know yet.

Dinwiddie is another key piece in that equation. He played at a near-All-Star level this year while Kyrie was out, and it looks like Brooklyn will try to weave him and Caris LeVert into the mix with Kyrie. If that balance works out, Dinwiddie could stay on long-term with Brooklyn. But if three guards turn out to be too many, or if a re-sign with Brooklyn doesn’t look to be in the cards because of the superstars, Dinwiddie could exercise his player option and head elsewhere for 2021-22.

19. Andre Drummond – Unrestricted

(via EssentiallySports)

(via EssentiallySports)

By all accounts from the Cleveland front office, the Cavaliers are hoping to retain Andre Drummond for the 2020-21 season. If that happens, and he waives his player option for next year, he’ll still be on the market in 2021. That leaves two big questions for the big rebounder – does Cleveland’s long-term rebuilding plan include a center whose playstyle seems less and less relevant, and if not, where could Drummond land next?

Despite being a killer on the boards, Drummond is a bit of a liability offensively (46.1 percent free-throw shooting for his career), and not the strongest defender for his size. That doesn’t mean there aren’t squads that could make great use of his abilities, but it does limit his options for the amount of money he could be asking. Teams like Atlanta, Charlotte, or Chicago – where rebounding has been a problem and there are fewer big stars taking up cap space – could be potential landing spots.

18. Lou Williams – Unrestricted

(via USA Today's FTW -

(via USA Today's FTW -

Next season will be a make-or-break time for the Clippers. After a hugely disappointing display in this year’s postseason, rumors are that the front office is intending to make some notable roster changes going into next year. While we don’t know what those will be yet, it’s possible that Lou Williams might not even spend the last year of his current contract in Los Angeles.

Whether or not he stays with the Clippers one more year, Williams could be a great acquisition for any number of teams when he enters free agency in 2021. If he stays in LA, and the Clippers win a title next year, a re-up seems likely. If the Clippers keep him and they fall short again, he’s likely to move on. His three Sixth Man of the Year awards and experience as a journeyman would make him a great fit anywhere, especially for squads that need veteran leadership off the bench. New Orleans? Denver? Boston? We’ll see.

17. Steven Adams – Unrestricted

Credit: Getty Images

Credit: Getty Images

Steven Adams has played his whole professional career in Oklahoma City, and he’s been a key piece of the Thunder’s continued greatness through numerous superstar departures and roster change-ups. He’s as much at the heart of that team now as anyone, and it seems almost unthinkable that he might leave in a year. But with OKC continuing with their long-term rebuild plans, and the amount of money Adams will be worth, it’s not a guarantee that he’ll stay.

If he opts to leave the Thunder, there are plenty of squads who’d jump for a center with his game IQ and toughness. Younger squads in need of size and defense (Atlanta, New Orleans) could make a play for him, as could any team looking to acquire a veteran five (Houston?). Or, of course, Adams could resign with OKC if they see him as part of their rebuilding efforts. If Chris Paul and Gallinari are gone, that might be more realistic. Thunder fans would surely like to see the big man stay.

16. Otto Porter – Unrestricted

Otto Porter

Otto Porter’s last two injury-ridden seasons have in many ways cast him out of the public eye. But he was, not so long ago, one of the most promising young players in the league, and he could retake that position in the future if he stays healthy. His next season in Chicago – assuming he waives his player option – will be telling. Now that Zach LaVine’s star is rising, how will the two mesh? The Bulls have a lot of potentials, but still a lot of questions.

There’s also the fact that Porter is expensive – set to make over $28 million next season. If he plays well with the up-and-coming Bulls and stays out of injury trouble, a re-sign from Chicago could certainly be worthwhile. But it’s not a guarantee. Unfortunately, the world just doesn’t quite know at this point what Porter is capable of. Hopefully, it won’t be too long before we find out.

15. Gordon Hayward – Unrestricted

Gordon Hayward 312

After this past postseason, Gordon Hayward remains one of the Celtics' biggest wildcards. On the one hand, his high price and history of injury, which carried into the playoffs this year, make him somewhat of a liability. On the other hand, he’s still a fantastic player, able to get his own shot on offense and open up huge opportunities for others on the perimeter.

Hayward has a player option for next season, which in all likelihood he will opt into. Beyond that though, nothing is certain. He’s a great presence on the floor, and his playing days are far from over, provided he stays healthy. But that risk, for the money he’ll be up for, may be too much for Boston to re-sign him as they keep developing younger talent. Either way, next season should be telling.

14. Mike Conley – Unrestricted

Mike Conley

Mike Conley’s first season in Utah wasn’t quite what anyone had hoped. His numbers all dropped notably from his last year in Memphis, and he couldn’t help the Jazz get past the Nuggets in the first round of the playoffs. Next year, he’ll be owed $34 million.

That doesn’t mean Conley’s washed – not by a long shot. But trade rumors surrounding the point guard suggest he might spend the last year of his contract somewhere else. If that’s the case, his free agency in 2021 opens up even more questions. Could he wind up in Philadelphia long-term? Would Utah make a play for Chris Paul, leaving him a temporary piece in OKC’s greater plan? Hopefully, wherever he winds up, Conley can reclaim some of that fire he had with the Grizzlies.

13. Jrue Holiday – Player Option

Credit: USATSI

Credit: USATSI

The New Orleans Pelicans will continue to be one of the most intriguing stories in the NBA going forward, mostly because we still don’t really know what Zion Williamson is capable of, but for other reasons too. Will Brandon Ingram keep improving and become a repeat All-Star? How will the team fare under Stan Van Gundy?

Out of all the questions circling New Orleans, Jrue Holiday is perhaps the surest thing the team’s got. On a defensively weak (to say the least) team, he’s the best defender by a country mile. He’s an elite playmaker, reliant scorer, and veteran locker room presence. But he could depart the Pelicans as early as 2021.

Whether or not he will, and where he could go, rely on many unanswered questions, like Lonzo Ball’s own future in New Orleans, and how the BI/Zion offensive chemistry shakes out. Holiday is a baller, and for a late-career contract, he’s likely to go where he’s likely to win.

12. Victor Oladipo – Unrestricted

Credit: Getty Images

Credit: Getty Images

Victor Oladipo’s trade prospects are being debated this offseason more than perhaps any other player. Injury streaks the last two years have kept the potential he showed in 2017-18 compelling, but not fully realized. Whether or not he stays in Indiana next season, he’ll be on the market come 2021, and his defensive prowess and proven ability in the clutch should make him appealing to most any team.

11. Kyle Lowry - Unrestricted



Kyle Lowry may be aging, but you wouldn’t know it by the way he played this season. Toronto re-signed him for a one-year deal at $30 million, but his future beyond 2020-21 is unclear. At his age, retirement wouldn’t be out of the question, but Lowry looked hungrier than ever this postseason, and there are certainly teams outside of Canada who’d love to have a veteran guard and defensive force like Lowry on their roster if the Raptors pass him up.

10. Derrick Rose – Unrestricted

(via Detroit Free Press)

(via Detroit Free Press)

A decade ago, no one thought Derrick Rose would wind up where he is now – coming off the bench in Detroit for $7 million a year. Injuries cut short one of the most promising careers in recent NBA history, but that doesn’t mean D-Rose’s story is over. Far from it; he averaged 18 points, 5.6 assists, 2.4 rebounds, and a steal in just 26 minutes per game this year – arguably his best season since before he tore his ACL.

Rose may never be an All-Star again, but he should remain a valuable veteran asset for a few more years to come. That means that when he enters free agency in 2021, a lot of teams could be interested. Having a solid back-up point guard with proven toughness and leadership ability would be great for some of the league’s promising young squads. It should be interesting to see what the rest of Rose’s career has in store.

9. Blake Griffin – Player option

Credit: Getty Images

Credit: Getty Images

Blake Griffin’s story isn’t all that different from Rose’s – a stylish, superstar-level player who couldn’t quite make it to the NBA Finals, was cut short of his peak by a string of injuries, and wound up playing for the Pistons. Unlike Rose, Griffin was an All-Star as recently as 2019, but more knee surgeries kept him sidelined during this past season. That leaves the 31-year-old’s future a bit of a question mark.

Griffin’s set to bring in $35 million next season with Detroit, and nearly $40 million the year after if he stays. Whether or not he does that will largely depend on his showing in 2021. If he looks washed, as many believe he is, he’s unlikely to opt-out of his Pistons contract. But if he comes back at an All-Star level, as he did in 2018-19, he could be a valuable asset to any team looking to make a deep playoffs run.

8. LaMarcus Aldridge – Unrestricted

LaMarcus Aldridge

LaMarcus Aldridge has done great things in San Antonio, being named an All-Star three times in a five year period where he’s averaged 8.2 rebounds and nearly 20 points per game. His rebounding and scoring numbers dropped marginally this season from the year before, but his stats were still solid across the board, and his three-point shooting jumped to 39 percent on an average of 3.0 perimeter attempts per game.

The fact, however, is that Aldridge is getting older. He’ll be 36 by the time his Spurs contract expires in 2021, and in a league where players with his skill set are less valued than they once were, that could leave his playing future uncertain. But the man can still ball. If Aldridge keeps developing his perimeter shot, he’ll be a boon most anywhere, even at his age.

A one or two year deal seems likely for teams with a bit of cap space and playoff potential. Alternatively, he could resign for that same amount of time in San Antonio, depending on the team’s long-term goals, and whether or not they put him on the trading table this offseason.

7. DeMar DeRozan – Unrestricted

(via Laredo Morning News)

(via Laredo Morning News)

Before the Spurs commit more money to LaMarcus Aldridge, they’ll likely want to make a play to retain DeMar DeRozan. While he hasn’t been an All-Star since he left Toronto, Aldridge had one of his best seasons yet this past year in San Antonio, averaging 22.1 points, 5.5 rebounds, and 5.6 assists on a career-best 54 percent shooting.

Those numbers could mean a return to the All-Star team with the Spurs next season, or it could mean DeRozan gets traded for some other assets as San Antonio looks to make changes after missing the playoffs for the first time in 23 years. Either way, DeRozan is sure to be in high demand when he enters free agency in 2021.

6. Rudy Gobert – Unrestricted

Credit: USATSI

Credit: USATSI

The Utah Jazz have some decisions to make going forward. Donovan Mitchell is clearly the future of the franchise, but how they adjust things around him to push for better postseason runs is up in the air. At the very least, it seems unlikely that they would trade Rudy Gobert after a season where he made his first All-Star team and averaged a double-double while shooting nearly 70 percent.

After next season though, it’s anyone’s guess. Rumors of friction between Gobert and other Jazz players have circulated before, and there are plenty of other squads that would kill to have his two-time Defensive Player of the Year-winning rim protection working on their behalf. Of course, depending on Utah’s plans, Gobert could wind up on one of those teams even before his current contract is up.

5. Chris Paul – Player Option

NBA Agent Thinks Chris Paul Is The Piece The Bucks Need To Retain Giannis Antetokounmpo

Chris Paul is owed $41 million next year, and $44 million the following year if doesn’t opt out of his deal. That’s a ton of cash, and despite how well he played this year, it’s likely more than OKC is ready to shell out while still in the middle of a rebuild. CP3 has been at the center of a bevy of trade rumors lately for that reason, and the speculation isn’t likely to die down any time soon.

Paul’s 2021 player option leaves even more unknowns on the table. If he’s traded to a contender like Miami or LA, there seems little chance he’d opt-out. If he gets picked up by a weaker team in exchange for some young assets and future draft power, he could leave after next season and re-sign for a year or two elsewhere – but that ability relies heavily on how he performs next season. If this year was any indication though, the Point God won’t be slowing down one bit.

4. Paul George – Player Option

(via EssentiallySports)

(via EssentiallySports)

The Clippers experiment failed this season. The team now has one more year to make it work before the superstars they traded their future for have the option to leave. Of course, if the rumors about LA’s front office looking to make big changes this offseason are true, Paul George’s uneven bubble showing could mean an even earlier departure.

George seems too good to keep bouncing around the league. But, despite the hit his reputation has taken lately, any city with the cap space would likely still jump at the chance to get him, either via a trade or free agency signing. A disappointing playoff performance doesn’t change that he’s still one of the NBA’s best wings, best defenders, and best marksmen, shooting a career-high 41.2 percent from deep this year.

3. Giannis Antetokounmpo – Unrestricted

Breaking: Giannis Antetokounmpo Has Won Second Consecutive MVP Award

Giannis’s free agency may only be a year out, but it feels like a lifetime away. His two-year streak of claiming the league MVP and failing to make the Finals has left the whole basketball world wondering what’s next. Will Milwaukee trade him before they lose him for nothing? Would he re-sign if they keep him and fall short again? At this point, he remains the player with the most promise in the league. And whether or not he stays with the bucks this coming season, it’s bound to be a free-for-all when he enters free agency in 2021.

2. Kawhi Leonard – Player Option

Credit: Getty Images

Credit: Getty Images

While half the basketball world wants to pull the trigger on condemning Kawhi’s LA move as a huge mistake, it’s still too early to tell. The Clippers feel immensely short in the bubble, and there are plenty of places to point fingers. While the organization makes shifts to do better next year – including a major head coaching change-up – Kawhi is the one piece that still feels untouchable.

He averaged career-highs in points (27.1) and assists (4.9) this year and made his fourth All-Star team in five years. He is still one of the two best two-way players in the league, and he is still squarely in the center of his prime. We don’t know what will happen next season or the season after. But any time Kawhi Leonard has the potential to enter the market, the very balance of the NBA is subject to change.

1. LeBron James – Player Option

Snoop Dogg Says LeBron James Is The GOAT Over Michael Jordan

All logic points the same way – LeBron James will end his career in Los Angeles. He just won his fourth championship and fourth Finals MVP with the Lakers, alongside another superstar who he seems to love like a little brother. LA is one of the two most accomplished and prestigious organizations in the NBA, and remaining there with AD, potentially through another one or two year contract after 2022, seems like LeBron’s best chance to stack his legacy even higher before retirement.

But logic has been wrong before. Michael Jordan played for the Washington Wizards, and Shaq left multiple championship teams. Those were different circumstances, of course. However, the possibility, no matter how slight, remains. Only two things are a hundred percent certain – LeBron James could leave the Lakers in 2021, and there are 29 other teams who would do nearly anything to get him.


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