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You Make This Trade Ten Times Out Of Ten

Let’s start by saying this: If Masai Ujiri could have won with a club led by Kyle Lowry and DeMar DeRozan, he would have gladly kept them together. If the Raptors could have achieved their goals without a super-duper star, Ujiri would have happily let it ride with what he had until everyone sailed off into retirement. Unfortunately, no matter how much depth Ujiri added to the roster, the top-line talent wasn’t enough to get through teams that had better top-line talent. Basketball is a strong link sport, where superstar talent has a disproportionate effect on winning, and so if you want to win, eventually you have to go out and get a superstar. 

With that in mind, Ujiri traded away the most loyal star that the Raptors have ever had (in a reportedly unnecessarily cold manner) in an attempt to secure one of the few true superstars in the NBA. When healthy and engaged, Kawhi Leonard is a perennial MVP and DPOY candidate, and even if he bolts Toronto a year from now in free agency, it was worth trading for him because when you have a chance to employ one of the best players in the NBA, you do it and figure out the rest later. These players are so scarce and so valuable, when you have a chance to employ one, you take it and then work like hell to keep him. 

Credit goes to Ujiri for managing to secure Leonard for DeRozan, Jakob Poeltl, and a heavily protected first round pick — a package that would appear to be on the weak end of what suitors in LA, Boston, and Philadelphia could have offered. It’s a smattering of assets that allows the Raptors to lose Leonard a year from now without feeling like they set themselves back in an eventual rebuild. Keep this in mind: the Raptors were probably not going to be able to keep pace with Boston and Philadelphia with a core of Lowry and DeRozan, and with DeRozan possessing an early termination option in his contract in the summer of 2020, the Raptors would have been very wary of signing him up for another tour of duty at max (or near-max) money. If that’s true, then Ujiri would have had to have been looking for an opportunity to trade DeRozan for value before that happened, meaning he was basically in an eighteen-month window where DeRozan was likely getting traded regardless. Getting a year to pitch a player of Leonard’s calibre on staying with the Raptors is about as good a return as you’re going to get for DeRozan, and that is not a slight to the player that DeRozan has become. The Raptors now have a Finals MVP that is currently in his prime, and if you want to play for real in the NBA, that’s the kind of player that you need. 

We can put it in even starker terms, too: 30 of the last 38 NBA titles have been won by Magic Johnson, Larry Bird, Michael Jordan, Kobe Bryant, Tim Duncan, LeBron James, and Steph Curry. If you don’t have a true superstar player, you have a hard ceiling on how high you can rise in the NBA. You’re either trying to get a guy as good as that, or you’re playing for second place. 

That’s about as cold an analysis as one can put on Wednesday’s transaction. It ignores DeRozan’s unfaltering dedication to Toronto and the Raptors organization. It ignores the possibility that Leonard doesn’t even report to the Raptors. It ignores the fact that Ujiri felt the need to keep DeRozan in the dark on this transaction. It ignores the possibility of the perception of the Raptors backsliding in NBA circles. It ignores the effect trading DeRozan will have on Lowry. It ignores the fact that a first-time NBA head coach will be largely responsible for compelling Leonard to stay beyond one season. It ignores the possibility that Leonard is too injured to return to being a top-flight player. It basically ignores all of the context that surrounds this trade, which no doubt several very talented writers will break down in the coming days. 

And you know what? None of it really matters when it comes to evaluating this trade. What’s the likeliest worst case scenario (because Leonard not reporting would cost him a lot of money, and remains unlikely): Leonard pouts through a year of Raptors basketball, and the team kick-starts a rebuild one year earlier than expected. They’ll take some reputational damage for ditching a loyal player, which isn’t nothing, but those sorts of things don’t tend to have lasting effects on well-run franchises. These are not non-risks, they’re just not the kinds of risks that should put a damper on this trade, because the potential upside — no matter how unlikely — is that high. Even if you operate from the assumption that Leonard leaves next summer, I still think this trade is a success because Ujiri went for it, he had a true superstar on his roster and will make his best effort to keep him. We know what the ceiling for Lowry-DeRozan is, we’ve seen it, but we have no idea what the Lowry-Leonard ceiling is, and it’s worth seeing what it is if the team is planning to head into rebuilding anyway in the next one-to-two years. 

Now, it’s obvious that that is not how Ujiri wants this to play out. Paul George eschewing expectations and staying in Oklahoma City — and not decamping for Los Angeles — no doubt gave Ujiri a glimmer of hope that he can actually make this work in Toronto. To do that he’ll need to not only seduce Leonard, but Leonard’s handlers, the group that played no small part in his rift with San Antonio. He’ll need to sell Leonard on the virtues of playing in a weak Eastern Conference, a conference where he could well be the best player. He’ll need to sell Leonard on the cache of young players that have been assembled, and hope that Pascal Siakam and OG Anunoby take big steps forward this season. He’ll need to help form a bond between Leonard and Lowry, and hope that Lowry is still engaged enough to play along. That’s a lot, and in these early hours after the trade became official, most think it’s too much to reasonably expect. 

A lot of the skepticism comes from just how silent Leonard has been for the last several months. His estrangement from the Spurs was almost entirely chronicled by Gregg Popovich and ‘people familiar with Leonard’s thinking.’ The word is that he has no interest in playing for the Raptors, much like he had no interest in playing for the Spurs. However, we act like he spent the whole season on the run from San Antonio, when in fact the deep rifts really didn’t start to emerge until pretty late in the season, and were no doubt exacerbated by Popovich’s snark and Tony Parker and Manu Ginobili’s comments in the press. We have no idea what Leonard’s feelings are versus what the feelings his people want out there. This is a lot of mystery surrounding a player that was hardly free with his emotions when he was still talking to the press. Given that, it is no wonder that most observers are negative about his state of mind regarding this trade. However, if one of his issues with San Antonio and his standing in the NBA was that he wasn’t featured enough as an endorser, quitting on one team and not reporting to another are not exactly the kinds of things that has major corporations lining up to be aligned with your brand. 

Still, for now the Toronto Raptors have acquired one of the best players in the NBA. The kind of player that you have to have to be real threat in this league, a fact not lost on a Raptors club that has been bounced by one man (swept twice) in the last three years. In a league dominated by top-shelf talent, you either have it or you don’t. The Raptors now have a top-five player, one that is arguably the best player in the east, with an All-Star point guard, and a strong stable of young talent to surround him with. On paper, it’s the best team the Raptors have ever had. 

Even if they’ll still probably be rebuilding that team twelve months from now. 

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