The case for staying
For the Raptors, their case is built on financial guarantees and an extra year of persuasion over Leonard’s other suitors.
On the financial end, the Raptors can offer Leonard a max offer of 5 years, $190 million. As far as long-term finances, no other team can match the Raptors offer given the NBA’s bargaining agreement.
Over the past six seasons, taking out his rookie year, Leonard has missed an average of 25 games each year, with the largest amount coming last season when he played in only nine games. Though some of his missed games are due to Gregg Popovich’s tendency to rest players, a majority were not.
With the health concerns that have plagued him in the past, locking up five years of guaranteed money would be very attractive.
As far as on-court reasons to stay, the Raptors possess a similar case to the Clippers, with upgraded pieces around the forward.
Kyle Lowry, the longest-tenured member of the franchise currently, is a quiet star. Even though he has made four All-Star appearances, the guard rarely is talked about among the NBA’s best point guards.
In his career, Lowry has averaged six assists per game and seven per game in his tenure with the Raptors.
The Raptors also have a host of two-way talent that is developing and ready to play alongside Leonard. Pascal Siakam, OG Anunoby, Fred VanVleet, are all getting better while Serge Ibaka, Jonas Valanciunas, and Danny Green are already solid contributors.
Playing in the East will also benefit the club as they will avoid the Golden State Warriors, Lakers and Houston Rockets in the playoffs prior to the NBA Finals.
Shown by his signing with New Balance, Leonard is also straying from the normal endorsement deals of his peers. If his trend of staying off the beaten path reigns true, staying in Toronto with a roster of other quiet producers would make sense.
Overall, the decision comes down to long-term security and added familiarity or trying to make it on the west coast alongside the stars of Hollywood.
A Larry O’Brien Championship Trophy with the Raptors would likely serve as the team’s best bargaining chip prior to the offseason.