Darren Abate/Associated Press

Former Toronto Raptors head coach Dwane Casey called the organization's decision to trade DeMar DeRozan to the San Antonio Spurs in the blockbuster Kawhi Leonard deal a "huge rolling of the dice."

Casey, who was fired by the Raptors in May and hired by the Detroit Pistons one month later, said Wednesday he understands the front office's decision to acquire the two-time NBA Defensive Player of the Year.

"For DeMar DeRozan, that's a hard pill to swallow," he told Sportsnet 590 The Fan. "Like him or love him, if you have any passion for the Toronto Raptors, it's almost like losing the Vince Carter—from a fan standpoint. From a pure basketball standpoint, it's hard to say you wouldn't want Kawhi Leonard on your team."

Like the rest of the league, the 61-year-old reigning NBA Coach of the Year is curious about whether Leonard can return to peak form after playing just nine games last season because of a lingering quad injury. The other factor is whether Toronto can convince him to sign a contract extension.

"The big question marks going to be, is he going to be healthy? Is he going to stay there?" Casey told Sportsnet. "If he does, it's a big coup for the front office and management. But those are huge questions, a huge rolling of the dice from that standpoint."

He added: "You've got to look at Kawhi's mindset. Most of all, his health. Is he going to be 100 percent healthy? I don't think anybody can answer that question until he runs out on the floor."

Video Play Button McCollum and the Blazers Snapped Postseason Losing Streak for "Jennifer" Stars Invest in Plant-Based Food as Vegetarianism Sweeps NBA The NBA Got Some Wild Techs This Season Jarrett Allen Is One of the NBA’s Hottest Rim Protectors Wade's Jersey Swaps Created Epic Moments This Season Westbrook Makes History While Honoring Nipsey Hussle Devin Booker Makes History with Scoring Tear 29 Years Ago, Jordan Dropped Career-High 69 Points Bosh Is Getting His Jersey Raised to the Rafters in Miami Steph Returns to Houston for 1st Time Since His Moon Landing Troll Lou Williams Is Coming for a Repeat of Sixth Man of the Year Pat Beverley Has the Clippers Stealing the LA Shine LeBron Keeps Shredding NBA Record Books Young's Hot Streak Is Heating Up the ROY Race with Luka LeBron and 2 Chainz Form a Superteam to Release a New Album Wade's #OneLastDance Dominated February Warriors Fans Go Wild After Unforgettable Moments with Steph Eight Years Ago, the Nuggets Traded Melo to the Knicks Two Years Ago, the Kings Shipped Boogie to the Pelicans ASG Will Be Competitive Again If the NBA Raises the Stakes Right Arrow Icon

Leonard possesses a player option in his contract that would allow him to become an unrestricted free agent after the 2018-19 season.

Chris Haynes of ESPN reported Wednesday the longtime Spurs standout has "no desire to play in Toronto," though. That raised questions not only about the ability to sign him to a new deal but also his willingness to suit up for the Raptors during the upcoming season.

Ultimately, trading for Leonard is an all-in move by the Raptors. They decided to undergo a major overhaul this summer, highlighted by the departures of DeRozan and Casey, despite posting the best record in the Eastern Conference at 59-23 last season.

LeBron James' decision to leave the East for the Los Angeles Lakers—Leonard's preferred landing spot, per ESPN's Adrian Wojnarowski—has left an NBA Finals void. A healthy, productive Kawhi could push them over the top but, as Casey warned, it's not a trade that comes without obvious risks.