Masai Ujiri made a calculated risk in trading for Kawhi Leonard

Over the years, Toronto Raptors president Masai Ujiri has built a prestigious reputation across the NBA. Take a look at his history, whether that be in Denver or with the Raptors. It’s undoubtedly impressive.

When Ujiri was brought back to Toronto in 2013 under the influence of then MLSE President Tim Leiweke, he inherited a head coach in Dwane Casey, an up-coming guard in DeMar DeRozan, and Kyle Lowry, who was still getting accustom to a new team, and city. Ujiri immediately left his mark by shipping out Andrea Bargnani and Rudy Gay in separate deals. Lowry was next, but a trade with the New York Knicks fell through. Ever since, Masai has been comfortable with his core, opting to tinker with the supporting cast instead of making any franchise-altering moves.

This summer, all of that changed. For the first time in his career as an executive, Ujiri was forced to make what he referred to as the most difficult decision of his life by firing the NBA’s Coach of the Year in Casey, and a man all but impossible to dislike. On Wednesday, the transformation continued, this time at the cost of DeRozan; the organization’s most important player since the Vince Carter era.

Regular season dominance only gets you so far. For the past five years, the Raptors constructed what appeared to be a complete team, only to come up short when it mattered most, largely due to LeBron James’ brilliance. Ujiri was perpetually loyal to the group he inherited until he no longer was.

In acquiring Kawhi Leonard from the San Antonio Spurs, Ujiri proved he’s willing to take on full responsibility from here on out, for better or for worst.

When healthy, Leonard is among the NBA’s most dynamic and complete players. If the Raptors get the past version of Kawhi, it’s a major win for Ujiri and the team. As beloved as DeRozan is in Toronto, he’s not on Leonard’s level. The biggest difference between the two comes on defense and from the three-point line. In nine years, DeRozan has shot .289 percent from deep, copulated with a true shooting percentage of .536. Kawhi is a career .386 three-point shooter, having managed a TS% of .597. On the other side of the ball, Kawhi’s defensive acumen is well-known, while DeRozan’s limitations have plagued him for years. From 2012 to 2017, Kawhi has been worth 24.2 defensive win shares in contrast to DeRozan’s 12.1.

Unlike DeRozan, Kawhi has been particularly effective in the postseason. In roughly the same amount of playoff games played as DeMar (52), Leonard has shot .433 from three, averaged an effective field goal percentage of .566, while contributing 8.4 combined win shares. In 51 games against Eastern Conference counterparts, DeRozan has shot .235 from deep, managed an eFG% of .422, while being worth a surprisingly low 1.6 win shares.

For the Raptors, Leonard is exactly the kind of player they need to reach the NBA Finals. With or without LeBron lurking in the Conference, it became clear that DeRozan wasn’t the same in the postseason. Giving up on him after one or two years is one thing, but after consecutive seasons of below average performance and abrupt playoff exits, it’s probably worth splitting up Lowry and DeRozan, and banking on someone like Leonard.

It’s rare for a player of Kawhi’s caliber to be made available. I can write all about his performance on the court, but it’s his health status, and a suddenly-turned toxic relationship with his former organization, that got us to where we are now. No one knows if Kawhi is fully healed from the quad issue that kept him out almost all of last season. ESPN did a nice job covering the details of the Leonard-Spurs timeline that eventually led to the 27-year-old revealing that he had no interest in signing an extension in San Antonio. Leonard, who has a player option next summer that he’s all but sure to opt out of, deemed the relationship irreparable, which forced the Spurs hand.

Leonard, born and raised in California, was said to want to play for the Los Angeles Lakers or Clippers. Other contenders with intriguing young assets, most notably the Boston Celtics and Philadelphia 76ers, were also heavily involved in trade discussions. The Spurs, not wanting to face Leonard in the Western Conference, entertained proposals from the Lakers, but ultimately preferred to trade their star to a team in the East. The Celtics were said to be unwilling to part with Kyrie Irving, Jayson Tatum, and Jaylen Brown among a few others, with the 76ers taking a similar stance with Joel Embiid, Ben Simmons, and Markelle Fultz.

Once the Celtics and 76ers moved on, and the Lakers figured they could just wait and sign Leonard next summer, Ujiri decided to jump in. DeRozan is no longer a young, up-and-coming star, but he has established himself as one of the NBA’s best guards. Jakob Poeltl is a solid prospect with room to grow, too. The return for the Spurs isn’t nearly as sexy as expected, but they did well enough and can move on. The Raptors deserve credit, as well. Along with Leonard, the Raptors acquired Danny Green; a savvy defender and three-point specialist with one year left on his contract. He should fit nicely in head coach Nick Nurse’s schemes and rotations. The 2019 first-round draft pick that Toronto sent is also 1–20 protected, and after one season, could turn into two second-round picks.

Reports have come out that DeRozan and Leonard are upset with the swap. Some media outlets have even gone as far as to speculate that Kawhi could hold out for all of 2019 and sign elsewhere as a free agent. It’s hard to imagine Ujiri would pull the trigger on a move of this magnitude without a strong feeling that Kawhi will report and play with the Raptors this coming season. I would say stranger things have happened, but if Leonard were to in fact refuse to play all 82 games with the Raptors, he would immediately become the league’s most polarizing player. Still, the same point remains: Ujiri traded for one of the league’s best athletes, and even though he had to give up a franchise icon to do it, Leonard and Green on the Raptors makes them legitimate threats to come out of the East.

As hard as it is to see someone like DeRozan go, even if Leonard were to leave after one season, the Raptors are a better team today than they were yesterday. It’s still within the realm of possibility that Masai works his magic and convinces Kawhi to stick around long term. As unlikely as that seems to be, nothing is certain, at least not this instant. With DeRozan gone, a new era, with or without Leonard in Toronto for more than one year, is on the horizon. Ujiri has managed to keep a promising nucleus of young talent including OG Anunoby, Fred VanVleet, Pascal Siakam, Delon Wright and to a lesser degree, Norm Powell. Even without a star in that mix (we don’t know what Anunoby will become), it’s a decent foundation to build on for the next few years. Lowry and Serge Ibaka have one year left on their contracts after this season, with Jonas Valanciunas and C.J. Miles both carrying 2019-2020 team options. If Leonard leaves, this group still has the looks of a lower seeded playoff team. It would also set Ujiri and the Raptors up very nicely for free agency in 2020 and 2021 with a class that could include Giannis Antetounkompo, Anthony Davis, Damian Lillard, Rudy Gobert, C.J. McCollum and Steven Adams, among others.

Over the years, Ujiri has done very little to set the Raptors back. He’s drafted well (Bruno Caboclo was a shot in the dark that didn’t pan out) and, outside of PJ Tucker, Masai has managed to resign and keep all of the team’s best players. One criticism, if proven to be true, could be his handling of DeRozan, who expressed feelings of betrayal after reportedly being told during the Las Vegas Summer League that he would stay with the organization. Admittedly, that’s not the best look, but if there’s anyone that would own up to such a thing, it would be Ujiri.

Acquiring a top-3 talent through trade in today’s NBA is unprecedented, even for an executive like Masai. As of today, Leonard brings a ton of baggage, and DeRozan’s presence on and off the court will be greatly missed, to be sure, but this is a business. The Raptors could no longer afford to stand pat.

It remains to be seen if Ujiri’s decision to bring in one of the NBA’s brightest, but most controversial stars pays off. If it doesn’t, it will all fall on one person, and Masai knows that. With a Conference ripe for the taking, Ujiri finally decided to go for it, and in doing so, made his most calculated risk to date.

Statistics courtesy of Basketball Reference



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