Monday, June 29, 2026

NBA Set for Summer of Chaos: LeBron, Kawhi, Gambling

Multiple superstars could change teams while the NBA prepares to hand down a ruling in the Clippers-Aspiration investigation.

Kirby Lee-Imagn Images

The NBA Finals were a fever dream for commissioner Adam Silver as the Knicks and Victor Wembanyama delivered blockbuster ratings and returned a halo the league had been missing for years.

Now, though, this offseason could be marked by absolute chaos. 

Monday morning indicated as much. 

Reporting continued to trickle out about a Clippers-Raptors trade for Kawhi Leonard, while the results of the league’s investigation into the relationship among Leonard, the Clippers, and Aspiration appear imminent.

Also Monday morning, NBA veterans Malik Beasley and Ed Davis became the latest players indicted in the federal gambling probe that has also led to the arrests of Chauncey Billups, Terry Rozier, and Damon Jones. 

And almost immediately after Beasley and Davis were indicted, ESPN reported that Draymond Green is declining his $27 million player option to enter free agency, giving the Warriors cap space to chase LeBron James as the organization attempts to chase one last ring with Stephen Curry. 

What to make of each development? 

End of Kawhi Era in L.A.?

The NBA has been investigating the Clippers’ relationship with failed environmental startup Aspiration for roughly nine months, with the saga hanging over the entire regular season. 

Silver indicated at his pre-Finals press conference on June 3 that the investigation was close to concluding. 

“I think we are close to the point now where I think we need to wrap this up, because you also need finality,” Silver said. “The team has to understand what situation they are going to be operating under, and so do the other 29 teams. So that’s where things currently stand.”

NBA teams can begin negotiating with free agents at 6 p.m. ET on Tuesday.

Should the Clippers be found to have violated the collective bargaining agreement, Silver has the ability to fine the organization, strip it of multiple draft picks, or void Leonard’s contract, the latter of which is perhaps the most relevant. 

Regardless of the ruling, if Leonard’s seven-year stint with the Clippers is over, it will be remembered more for what happened off the court.

Leonard has one year left on his current deal worth $50.3 million. In July, he is eligible for a two-year extension worth $123.7 million. On Monday, ESPN reported that the Raptors are the only team Leonard would sign a long-term extension with other than the Clippers.

While no NBA ruling has been made as of Monday afternoon, it’s hard to see the Clippers and Raptors being deep into talks without an indication that the league would approve a trade that includes his contract. 

An NBA spokesperson did not respond to a request for comment on the Aspiration investigation or whether Leonard’s contract is tradeable. 

Leonard led the Raptors to the 2019 championship in his lone year with the organization after requesting a trade from the Spurs. 

He left to sign with the Clippers and hasn’t been back to the Finals since. Leonard turned 35 on Monday and is coming off a strong season in which he averaged 27.9 points per game in 65 games. 

Two More Players Added to Betting Probe

Beasley and Davis became the latest players involved in the federal gambling probe, another off-court headache for Silver and the league. While the Aspiration saga is close to ending, the gambling probe will stretch into next season at a minimum.

Rozier’s case is set to go to trial in February 2027, while the judge in Billups’s case wants that trial to start in November. Jontay Porter, who pleaded guilty in July 2024, is still awaiting sentencing, and Beasley and Davis have yet to surrender to authorities as of Monday afternoon. 

Their indictments extend the probe’s presence over the NBA, especially if their cases go to trial. While the NBA has fully cooperated with federal authorities, the case could threaten the league’s positive momentum and show the full scope of its gambling issues.

Silver was one of the first major advocates for widespread legalized sports betting after publishing an op-ed in The New York Times in 2014. In October, Silver said on The Pat McAfee Show that the league asked sportsbooks to pare down their prop betting options. Multiple U.S. sportsbooks have already eliminated prop bets for NBA players on two-way and 10-day contracts in light of Porter’s case. The NBA has also changed its injury report process with teams to have them update players statuses on game days. Silver has also said he wants more federal regulation in sports betting. 

New-Look Warriors Superteam?

Leonard isn’t the only star who could be in a new uniform by summer’s end. 

Green’s decision to elect free agency Monday makes Golden State the potential epicenter for free agency. ESPN reported the team is trying to sign both James and Anthony Davis to pair with Stephen Curry in the twilight of their careers. Davis is set to make $58 million this season, and finding the players to match his salary in a trade won’t be easy. 

James and Green share an agent in Klutch’s Rich Paul, and both would have to take discounts to make a Big 4 work for the Warriors.

Should it become reality, the Warriors would be a fascinating experiment within the league and a likely ratings behemoth. The team would be assembling four players ages 33 and older to contend with the younger cores of the Spurs, Thunder, and Knicks. It would also mark an odd coda to the James-Curry battles that dominated the NBA last decade. Both players would team up to chase a fifth ring after Curry won three of his four against James, while James led the 2016 Cavaliers to a 3–1 upset over Curry’s Warriors for his most memorable title. 

The Celtics are listening to offers for All-Star Jaylen Brown after failing to acquire Giannis Antetokounmpo in a package centered on him. Brown has one of the richest contracts in league history. He’s about to enter the third year of a five-year, $304 million supermax he signed back in 2023. In July, he’s eligible to have two years worth $142 million tacked onto the deal, which will pay him more than $70 million annually in his ages-33 and -34 seasons. 

Brown is set to make $57 million next season. Similar to Davis, any team interested in trading for Brown might have to deplete its depth to match his salary in a trade, limiting his market.

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Unrivaled Lands Two International Stars Amid Project B Battle

Unrivaled also signed Canadian forward Bridget Carleton.

Malik Beasley Latest NBA Player Indicted in Federal Gambling Probe

Beasley coordinated with Ed Davis to fix games, according to the indictment.
Jun 17, 2026; Phoenix, Arizona, USA; Las Vegas Aces guard Chelsea Gray (12) against the Phoenix Mercury at Mortgage Matchup Center. Mandatory Credit: Mark J. Rebilas-Imagn Images
Exclusive

WNBA Star Chelsea Gray to Join Prime Video as Player Contributor

Gray is the latest active player to join the media.

After NFL and CFL Say No, UFL May Be Sorsby’s Best Option

The UFL appeared to confirm Sorsby would be eligible.
podcast thumbnail mobile
Front Office Sports Today

6/29/26 – South Korea’s World Cup Crisis, Brandon Aiyuk Holdout, Alyssa Thomas Suspended, Jaylen Brown Fires Back

0:00

Featured Today

June 26, 2026

In an Era of $1,000 Tickets, $10 Watch Parties Bring Fans Together

Stadium watch parties now rival home-game experiences.
June 25, 2026

Italian Americans Have Severe World Cup FOMO

Bars and restaurants in Boston, Philly, and beyond are missing the Azzurri.
Indiana Fever guard Lexie Hull (10) celebrates a three-point basket Monday, June 22, 2026, during the game at Gainbridge Fieldhouse in Indianapolis. The Indiana Fever defeated the Phoenix Mercury, 86-77
June 24, 2026

Female Athletes Are Trying to Build the ‘Athleisure of Beauty’

“Performance cosmetics” have emerged alongside the women’s sports boom.
June 18, 2026

Why U.S. Open Host Sites Are on a 25-Year Plan

The U.S. Open has already picked out 22 future sites through 2051.
Jun 24, 2026; New York City, New York, USA; Norway national soccer team fans show support accompanied by Mr. and Mrs. Met during the MLB game between the New York Mets and the Chicago Cubs at Citi Field.

World Cup Fans Are Taking Over MLB Stadiums

About 8,000 Scottish fans attended the Marlins game Monday night.
Feb 24, 2026; Tempe, Arizona, USA; Los Angeles Angels A general view of the MLB logo and first base during the first inning of a spring training game between the San Francisco Giants and Los Angeles Angels at Tempe Diablo Stadium. Mandatory Credit: Allan Henry-Imagn Images
June 26, 2026

MLBPA: Owners’ Aggressive Labor Proposals Unite Players

The union has decried the perceived attack on “player choice.”
Apr 9, 2026; New York, New York, USA; New York Knicks center Mitchell Robinson (23) secures a rebound during the fourth quarter against the Boston Celtics at Madison Square Garden. Mandatory Credit: Lucas Boland-Imagn Images
June 26, 2026

Knicks Face Second Apron Squeeze After Title

Mitchell Robinson has likely played his final game for the Knicks.
Sponsored

How Daktronics Is Reshaping the Modern MLB Ballpark Experience

The technology powering baseball’s next chapter.
Jun 14, 2026; Washington, D.C., USA; Justin Gaethje (blue gloves) celebrates after winning the UFC Freedom 250 fight against Ilia Topuria (not pictured) at the White House South Lawn. Mandatory Credit: Amber Searls-Imagn Images
June 26, 2026

UFC Touts 34M Global Audience for White House Event

The event’s overall audience doubles with the inclusion of international figures.
June 25, 2026

MLB Owners Escalate Labor Fight With New Contract Proposal

MLB team owners make another radical labor proposal.
FILE PHOTO: A view shows the logo of PGA Tour during the Canadian Open Championship at Oakdale Golf and Country Club in Toronto, Ontario, Canada June 7, 2023. REUTERS/Nick Lachance/File Photo
June 25, 2026

PGA Tour Faces New Sponsorship Test With 2028 Overhaul

Championship Series events will have $20 million purses.
Phoenix Mercury forward Alyssa Thomas (25) scrambles to get up over Indiana Fever guard Caitlin Clark (22) on Wednesday, June 24, 2026, during a game at Gainbridge Fieldhouse in Indianapolis. The Phoenix Mercury defeated the Indiana Fever, 111-109.
June 25, 2026

Caitlin Clark’s Status Unclear After Apparent Throat Punch, Back Injury

The WNBA gave Alyssa Thomas a one-game suspension on Thursday.