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Points of concern in a Kawhi Leonard deal

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Kawhi Leonard is one of the best players in the NBA, but trading for him comes with significant risk.

San Antonio Spurs v Golden State Warriors - Game One Photo by Thearon W. Henderson/Getty Images

The offseason rumor mill is churning to full speed as we approach the beginning of free agency, and one of the major dominoes likely to fall emerged at the forefront of the news today: Kawhi Leonard. ESPN’s Brian Windhorst, Ramona Shelburne and Adrian Wojnarowski shed some light on trade negotiations involving the Spurs star and confirmed that the Boston Celtics are one of several teams to have submitted an official offer.

The case for bringing in Leonard is quite simple: when healthy, he’s one of the five best players in the NBA—and that might be understating things. His resume speaks for itself: two Defensive Player of the Year awards, two All-Star appearances, two First Team All-NBA selections, two top-three MVP finishes, and the 2014 NBA Finals MVP. Leonard is already well on his way to a Hall of Fame resume, and at only 26 years old, his book is far from fully written.

NBA: Cleveland Cavaliers at San Antonio Spurs Soobum Im-USA TODAY Sports

As you might have heard, though, there are extenuating circumstances behind Leonard’s availability this summer. Players of Leonard’s caliber simply don’t hit the trade market if everything is peachy. While the upside of a Celtics team with Leonard in the starting lineup is significant, the situation surrounding him is particularly messy, and there are a number of factors Danny Ainge and company will need to consider before pulling the trigger on a trade.

We’ll start with the most obvious: Leonard played only nine games last season, and he was the focal point of perhaps the most bizarre soap opera in basketball. The exact details of what has transpired between Leonard and the Spurs are still unclear, but the framework for the tension seems apparent—struggling with a nagging hamstring injury, Leonard grew discontented with the Spurs and how their medical staff managed his rehab, creating a rift between the player and the team that only seemed to widen as the season went on.

This is hardly the first time a player and franchise have gone through this kind of tension—just last summer, it looked as though LaMarcus Aldridge was going to force his way out of San Antonio before Gregg Popovich’s intervention smoothed things over—but the way the conflict progressed was downright bizarre. Popovich and the Spurs’ coaching staff seemed perpetually uncertain of exactly what Leonard’s status actually was. It seemed as though communication between Leonard’s camp and the organization was borderline nonexistent. We may not have the full picture of what happened behind the scenes, but skepticism of Leonard’s camp reliably communicating his intentions seems justifiable.

NBA: San Antonio Spurs at Denver Nuggets Isaiah J. Downing-USA TODAY Sports

Leonard’s health concerns outstrip even the bizarre nature of his feud with the Spurs. He doesn’t typically get slapped with the ominous “injury-prone” label like Anthony Davis or Blake Griffin, but perhaps he should be—he’s played more than 70 games in a season only twice in his seven-year career. It’s not uncommon for players who struggled to stay on the court early in their career to overcome those issues as they mature (see: Curry, Stephen), but Leonard’s extended absence this season calls into question his ability to stay on the court with regularity. Trading for 50 or 60 games of Kawhi Leonard is a different conversation than trading for 70 or 80.

As if the injury concerns weren’t enough, Leonard is also likely to hit unrestricted free agency next summer, with a player option he will almost certainly decline. This is an even more muddled proposition for a front office trying to make a deal, because the team is essentially forced to either take a verbal commitment to a new contract at face value or roll the dice without one and hope they can convince him to re-sign. Reports have connected Leonard to the Los Angeles Lakers for some time, and the Spurs situation has shown very little reason to count on Leonard’s camp for reliable communication, which makes a verbal commitment feel flimsy at best. Trading for one season of Kawhi Leonard is a different conversation than trading for five.

Even in isolation, any one of these factors would be a substantial consideration in this kind of trade. Last summer, the Pacers dealt Paul George for the (at the time) disappointing return of Victor Oladipo and Domantas Sabonis, their leverage relatively crippled by George’s pending free agency and widely reported desire to play for Los Angeles—and the Thunder may very well lose him to the Lakers this summer. Meanwhile, Jimmy Butler—an MVP contender in his own right this season before injuring his meniscus, with an additional year remaining on his deal—netted only a rehabbing Zach LaVine, an underwhelming Kris Dunn, and a first-round pick swap. Neither of those two are on Leonard’s level as individual players, but the circumstances surrounding them were not nearly as complicated.

None of this is to say that the Celtics should avoid Leonard at all costs. The opportunity to add a player of his caliber is something that deserves the fullest exploration by Ainge and the front office. It’s not an open-and-shut deal, however, and the balance between risk and reward will sit on a razor’s edge.

NBA: Playoffs-Cleveland Cavaliers at Boston Celtics Bob DeChiara-USA TODAY Sports

Jaylen Brown may never reach Leonard’s heights as a player, but his ceiling is still very much undefined at only 21 years of age. Parting with several years of a young, blue-chip wing player for potentially only one season of Leonard is a tough pill to swallow. Gordon Hayward could be a reasonable price, as Leonard is a one-to-one upgrade, and we don’t know how Hayward will look in his return from injury just yet. However, Hayward is also already locked up in the long term, and trading him after such an involved rehab process from his dramatic injury would risk fracturing the fanbase and the locker room. Kyrie Irving will hit free agency at the same time as Leonard, but he plays a different position, and a one-for-one trade will pose challenges to maintaining a balanced roster. Any of these deals will also diminish the Celtics’ vaunted stash of future draft picks.

Danny Ainge’s inaction at certain moments prior to last summer’s Irving-Isaiah Thomas blockbuster became something of a running joke in NBA circles, but it is indicative of his philosophy as a GM: he’s unwilling to take deals he’s not likely to “win” and refuses to overpay. This is why I find a Kawhi Leonard trade unlikely for the Celtics—there are simply too many conceivable outcomes where such a trade works out poorly for Boston in the short term and long term for Ainge to find it particularly appealing.

Kawhi Leonard is one of the most unique and game-changing talents in the NBA, but with all the complicating factors surrounding his potential exit from San Antonio, a trade to acquire him is a massively risky undertaking. Unless the Spurs are willing to settle for much less than you’d generally expect in return for such a player, I have a hard time imagining him in Celtics Green this coming season.