It's safe to say the Toronto Raptors have had a lot of wins this off-season.From the blockbuster trade that brought Kawhi Leonard back to Toronto, the selections of Allen Graves and Jaden Bradley in the NBA Draft, and the bargain sigining of Kyle Anderson to round out their second unit, there is plenty to be excited about.However, not everyone experienced this good fortune. Here's a recap of the winners and losers from the Raptors offseason.Winner: Kawhi LeonardMar 1, 2019; Toronto, Ontario, CAN; Toronto Raptors forward Kawhi Leonard (2) during their game against the Portland Trail Blazers at Scotiabank Arena. The Raptors beat the Trail Blazers 119-117. Mandatory Credit: Tom Szczerbowski-USA TODAY Sports | IMAGN IMAGES via Reuters ConnectLeonard might be one of the biggest winners in the NBA this offseason. He is coming off of a season in which he averaged 27.9 points, 6.4 rebounds, and 3.6 assists per game while shooting over 50 per cent from the field and 38.7 per cent from beyond the arc at age 34. Despite that, the Clippers finished at just 42-40 at the end of the regular season, which was good enough for the 9-seed in the Western Conference. They still fell short to the Warriors in the first round of the play-in and missed the playoffs.Leonard now joins a Raptors squad that was 15 minutes away from a playoff series victory against the Cleveland Cavaliers, and one Kawhi Leonard away from being a stacked team in what is shaping up to be an up for grabs Eastern Conference.Winner: Sandro MamukelashviliFeb 8, 2026; Toronto, Ontario, CAN; Toronto Raptors forward Sandro Mamukelashvili (54) sets to shoot against the Indiana Pacers at Scotiabank Arena. Mandatory Credit: Kevin Sousa-Imagn Images | IMAGN IMAGES via Reuters ConnectMamukelashvili is another winner this offseason, even if he departed from Toronto. He got paid, as the Lakers gave him a four year deal worth $52M. In addition to this, he gets to play alongside Luka Doncic and Austin Reaves. The Lakers lost Rui Hachimura to the Clippers, and with LeBron James appearing to be gone as well, Mamukelashvili also has a much clearer path to more minutes with the Lakers than he did with the Raptors.Losers: Jamison Battle and Trayce Jackson-DavisMar 23, 2026; Salt Lake City, Utah, USA; Toronto Raptors forward Jamison Battle (77) shoots the ball during the second half against the Utah Jazz at Delta Center. Mandatory Credit: Chris Nicoll-Imagn Images | IMAGN IMAGES via Reuters ConnectJamison Battle made the most of his playoff minutes despite having a fairly limited role. He showed a lot of potential off the bench as a sharpshooter. Jackson-Davis did not have a clear path to minutes last season with the emergence of Mamukelashvili, but things were looking up with him set to receive a big payday outside of Toronto.However, the Raptors brought in Kawhi Leonard, Allen Graves and Kyle Anderson to their frontcourt. Brandon Ingram got sent off to the Clippers in the Leonard trade which clears things up a little bit, but Scottie Barnes isn't going anywhere. This combined with the emergence of Collin Murray-Boyles means that Battle and Jackson-Davis could find themselves as the odd man out.Loser: Gradey DickJan 14, 2026; Indianapolis, Indiana, USA;Toronto Raptors guard/forward Gradey Dick (1) in the first half against the Indiana Pacers at Gainbridge Fieldhouse. Mandatory Credit: Trevor Ruszkowski-Imagn Images | IMAGN IMAGES via Reuters ConnectDick has a real opportunity at a fresh start. After losing minutes over the past few years in Toronto, that might be what he needs to break out.While this makes him a winner in that he may get more minutes than he would have with the Raptors, he was essentially a throw-in for the Kawhi Leonard trade, and he is now tasked with learning a new system. He likely is not in the Clippers future plans, and if he does do well, there is a good possibility that Dick would be on the move yet again.Sign up for our free newsletter, which will bring all Toronto Raptors On SI stories every weekday to your email.Add us as a preferred source on GoogleFollow