The NBA’s investigation into Kawhi Leonard’s previous contract with the Los Angeles Clippers may not be resolved before the start of the 2026-27 season, creating uncertainty around his agreed-upon trade to the Toronto Raptors.
According to John Hollinger of The Athletic, the league’s investigation is only the first stage of what could become a lengthy legal process under the NBA’s collective bargaining agreement. Even after investigators complete their findings, any cap-circumvention case would proceed before a system arbitrator and could then enter an appeals process before commissioner Adam Silver is able to impose discipline.
That timeline raises the possibility that Leonard could still officially be a Clipper when training camps open in October, despite the June 30 agreement that would send him back to Toronto.
The Raptors and Clippers have voluntarily delayed completing the trade while the NBA examines whether Leonard’s 2021 endorsement agreement with financial technology company Aspiration violated league rules governing player compensation. Clippers owner Steve Ballmer had invested in the company, prompting questions about whether the arrangement provided Leonard with impermissible benefits outside his NBA contract.
Toronto has publicly projected confidence throughout the process. TSN’s Josh Lewenberg recently reported that the Raptors believe the only outcome likely to jeopardize the trade would be the highly unlikely scenario of Leonard’s current contract being voided. League observers continue to view that as the least probable outcome.
Under the agreed framework, Toronto would acquire Leonard in exchange for Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a 2027 first-round pick swap and two second-round selections. Until the investigation concludes, however, Ingram and Dick technically remain Raptors while Leonard remains under contract with the Clippers.
Hollinger noted that a prolonged process could leave both franchises operating in limbo throughout the offseason. He also questioned whether potential league penalties lose their intended impact as time passes. For example, voiding Leonard’s contract would carry less weight now that only one season remains on the deal, while the Clippers have already used what could have been their most valuable forfeitable asset—the No. 5 overall pick in the 2026 NBA Draft, which became Illinois guard Keaton Wagler.
Future draft assets, however, could still be subject to league discipline if wrongdoing is established. Hollinger pointed to the Clippers’ future first-round selections, including Indiana’s 2029 pick and Los Angeles’ own picks from 2030 through 2033, as possible penalties that would remain available to the NBA.
The Raptors also accepted significant risk by agreeing to the trade before the investigation concluded. Hollinger noted that Toronto understood the ongoing inquiry and still elected to pause much of its offseason activity while waiting for clarity. If Leonard were eventually suspended or faced another unexpected penalty, the Raptors would need to adjust after already committing substantial assets to the transaction.
From a basketball perspective, Leonard remains one of the league’s elite two-way players. He averaged 27.9 points, 6.4 rebounds, 3.6 assists and 1.9 steals in 65 games during the 2025-26 season while shooting 50.5 percent from the field, 38.7 percent from three-point range and 89.2 percent from the free-throw line. He earned All-Star honors, made the All-NBA Second Team and finished seventh in MVP voting.
Toronto finished 46-36 last season and earned the Eastern Conference’s fifth seed before losing a seven-game first-round playoff series to Cleveland. The franchise continues to believe Leonard can help elevate it back into contention, but with the investigation potentially extending into the regular season, both the Raptors and Clippers may have to begin 2026-27 without certainty about one of the offseason’s biggest blockbuster deals.
