Kawhi Leonard and the Clippers: A millionaire failure in Los Angeles

Steve Ballmer’s Era with the Clippers: A Million-Dollar Investment with Questionable Results

On August 18, 2014, Steve Ballmer, then CEO of Microsoft, euphorically celebrated in front of a crowd of 4,500 fans at the Staples Center in Los Angeles. He had paid a record figure of $2 billion for the Los Angeles Clippers, a move that promised to rescue the team, the city, and the NBA from a dark era.

“Let’s be bold. Bold means taking risks,” Ballmer declared. “Let’s be optimistic. Let’s be relentless. Nothing will stand in our way: boom! The relentless Clippers. That’s us.”

Steve Ballmer

Eleven years later, Ballmer’s bet on the championship, or even the first appearance in the NBA Finals, has not materialized. Since the arrival of Kawhi Leonard in 2019, the team has only won three playoff series, and Leonard has played in 58% of the games. But the failure goes further. The Clippers have faced unprecedented scrutiny from the league and the rest of the NBA. They have been the subject of two lawsuits for alleged manipulation violations, fines, and at least three NBA investigations, the most recent focusing on allegations that the team evaded the salary cap. This latest investigation, which examines a $28 million sponsorship deal for Leonard with Aspiration, a company in which Ballmer invested $50 million, has cast a shadow over the team. The Clippers tried to bolster their roster, meeting with Chris Paul, adding Bradley Beal, James Harden, John Collins, and Brook Lopez. However, the team’s center remains Leonard, who will receive $50 million next season. Several rival executives consider that the initial investment in Leonard, despite its high cost, was a smart decision. However, they are now evaluating the return on that investment in a similar way.

“Looking back, the deal was a disaster,” said a rival general manager.

Rival General Manager

Interviews with team sources, former employees, rival executives, and agents reveal how the team, desperate for a star and relevance, surrendered to Leonard and his entourage, seeking to keep him happy and healthy, even at the cost of an internal culture of fear and secrecy, and a series of legal battles and accusations of misconduct.

“This latest investigation is different,” said a former Clippers staffer about the league’s investigation into the sponsorship deal. “This directly questions Steve Ballmer’s character. At some point, Steve has to get out of the Kawhi business.”

Former Clippers staffer

The Arrival of Kawhi Leonard: A Complicated Deal

On July 5, 2019, Clippers executives gathered in a conference room in El Segundo, California, with great anxiety. They had been pursuing Kawhi Leonard for years, and they feared that, at the last minute, he would reject them for the Lakers. After meeting with Leonard, they agreed to acquire Paul George from Oklahoma City. The final deal involved the transfer of Shai Gilgeous-Alexander, Danilo Gallinari, five first-round picks, and two pick swaps. Ballmer was concerned about the number of picks the team was giving up. Some staff members feared the deal would have consequences similar to the 2013 trade between Boston and Brooklyn. The Clippers were also nervous about trading Gilgeous-Alexander. However, Leonard, who had just won a title with the Raptors, was not interested in waiting for the development of a young player. Acquiring George was one of several requests from Leonard and his entourage, led by his uncle, Dennis Robertson. These requests included a stake in the team’s ownership, access to a private plane, a house, and guaranteed off-court sponsorship money. Robertson also requested that Leonard could initially live in San Diego, skip some media obligations and community events, and that the team promise to market Leonard individually. The Clippers agreed to these conditions. Robertson also demanded a strict protocol on how to talk about Leonard publicly, limiting information. The Clippers, seeking to be a star-friendly organization, agreed. On July 5, 2019, a magnitude 7.1 earthquake shook Ridgecrest, California, as the team was about to close the deal. Almost three hours later, Leonard informed the teams of his decision to sign with the Clippers, and the George trade became official. The excitement spread through the franchise, but a feeling of fear also began to emerge that would define the team’s culture.

Since 2019, the Clippers have faced two separate lawsuits involving Leonard. They have been fined at least twice by the NBA for violations related to Leonard. There have also been at least three NBA investigations into the Clippers involving Leonard.

The Fear of Bothering the Star: The Culture of Secrecy

NBA teams often fear upsetting their stars, and this dynamic intensified with Leonard’s arrival in Los Angeles. The Clippers were desperate to prove they could please star players, moving away from the problematic Sterling era. In the first game of the season, Leonard was absent due to “load management” due to a left knee injury. Coach Doc Rivers stated that Leonard felt fine, but the league initiated an investigation. The NBA fined the Clippers for statements inconsistent with Leonard’s health, revealing details about his patellar tendinitis. This sent shivers down the organization. The Clippers knew that if Leonard could lose trust in the Spurs, he could also do so with them. The situation generated an atmosphere of secrecy and fear. Information about Leonard’s health became a sacred secret, creating a division between those who knew and those who didn’t. In an effort to please Leonard, public statements and social media posts mentioning him were subjected to intense scrutiny, even by Leonard’s circle. This created tension among the staff.

“There was a very marked sensitivity,” said a source.

Source

“Everyone was so tense… I’m telling you, when I say tense, I mean tense,” said another.

Source

The Clippers issued a statement in which they stated that they treated Leonard with the same respect as all their players and staff, and that they were grateful for his work.

Stephen A. Smith reacts to Steve Ballmer’s interview with Ramona Shelburne following the Kawhi Leonard report.

Contract Extensions and the Uncertain Future

Leonard was eligible for a contract extension for the 2023-24 season. The team prioritized salary flexibility, especially due to restrictions, partly due to extension talks with George. The Clippers knew about Leonard’s health, and if this was the amount they were going to pay him, there was a good reason.

“We know what’s under the hood,” said a team source.

Team source

In January 2024, Leonard agreed to a three-year contract for $153 million. Although he played 68 games in the regular season, the team seemed prepared for another playoff run. However, an inflammation in his right knee forced him to miss the last eight games and he only played two games in the playoff series against Dallas. Leonard was hoping to play for Team USA in the Paris Olympics, but his physical condition was uncertain. Team USA officials were surprised to learn of a procedure on his knee, which was not made public until months later. At training camp, Leonard looked “slow and labored.” The Clippers coach, Tyronn Lue, and the president of basketball operations, Lawrence Frank, emphasized that Leonard wanted to play, but Team USA officials were not convinced. Leonard was replaced by Derrick White on the roster, who won the gold medal at the Paris Olympics. Team USA officials regretted the situation.

Team USA officials learned in late June 2024 that Leonard’s camp had not been forthcoming about a procedure that had been performed on his knee in early May, nearly two months earlier.

Randy Shelton’s Lawsuit and Investigations

On October 10, 2024, Randy Shelton, former Clippers strength and conditioning coach, filed a lawsuit against the team and Frank. Shelton alleged manipulation to acquire Leonard, wrongful termination, and issues with the handling of Leonard’s health. He also alleged that Leonard suffered injuries that the team did not publicly disclose. Shelton alleged that Robertson negotiated his contract as an unlicensed agent. His lawyers added that Shelton received a “direct threat” from Robertson. The Clippers denied Shelton’s accusations and sought to resolve the matter through arbitration. The team fired Shelton in July 2023. In the lawsuit, the team stated that Shelton was unwilling to do the work for which he was hired. A team source said that many of Shelton’s claims were false, but not all. The source added that there was concern about the incomplete information about Leonard’s health that Shelton shared. In his lawsuit, Shelton alleged that the Clippers violated tampering rules in their pursuit of Leonard. A former Clippers employee said that Shelton’s lawsuit presents new problems for the team, especially if internal statements and communications are made public.

Leonard, 34, has played in only 58% of the Clippers’ games since 2019, and the team has only won three playoff series in that time.

Leonard’s Control of the Environment

On December 7, 2024, reporters gathered at the Clippers’ new training facility in Inglewood watched Leonard practice. Leonard had not played all season due to inflammation in his right knee. The question of when he would return to the game hung over the team. Upon noticing the media, Leonard hesitated. Robertson, standing next to him, gestured to stop the filming. Team officials asked the media to stop filming. A former staff member said Leonard wanted to control the environment. After Leonard’s arrival, reporters found that even when they asked privately about Leonard’s health, they were often directed to contact his entourage, which meant contacting Robertson. Robertson has long been Leonard’s spokesperson. His role in Leonard’s life became more pronounced after the death of his father, Mark, in 2008. Robertson played college basketball and then spent nearly three decades as a banking executive. In a photo of the Raptors team, Robertson was in the last row, being the only family member in the photo.

Leonard’s Return and Information Protection

On January 3, 2025, the league released an injury report. The Clippers listed Leonard as out for the game against the Atlanta Hawks. Less than three hours later, NBA journalist Chris Haynes tweeted that Leonard expected to debut against the Hawks. Three minutes later, the Clippers’ public relations account posted an update on X: Leonard had been upgraded to questionable. On the night of the game, Lue faced a large media crowd. Lue announced that Leonard would be subject to a minutes restriction, but did not reveal the restriction. This response became commonplace for Lue, protecting information about the star and avoiding legal issues.