Negotiations are expected to begin in the near future, with Gaines having served as Leonard’s business attorney over the past year. The timing aligns with Leonard entering the final season of his current contract and being eligible for an extension that could reach up to $123.7 million over two years.
This marks a shift in Leonard’s representation, ending a longtime arrangement. He was previously represented by Mitch Frankel, along with his uncle and longtime adviser, Dennis Robertson. Frankel handled contract negotiations during Leonard’s time with the Clippers, including a three-year extension signed in 2024.
Leonard is entering a season that will pay him $50.3 million. Toronto’s willingness to offer an extension has reportedly been a key factor in Leonard’s decision to pursue a return to the Raptors.
The recent blockbuster trade that brought Leonard back to Toronto includes several assets: Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a first-round pick swap in 2027, and two second-round selections. Leonard’s desire to play in Toronto has helped shape the trade market, with multiple teams showing interest before the NBA Draft. However, once it was clear Leonard preferred a short-term, Raptors-focused extension, some interested clubs decided not to pursue longer commitments.
There were basketball considerations as well. Leonard’s familiarity with the Raptors organization, his affinity for the city, and his belief that Toronto can emerge as a legitimate contender in the Eastern Conference all played a role in the decision to return.
For more hoops coverage, readers can explore ongoing discussions about NBA free agents by position and related developments as the season approaches.
