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Masai Ujiri wants to win. Does that mean he’ll trade Kyle Lowry?

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Rumours are already swirling! Does Ujiri owe it to himself to find a better #2 before the Raptors’ window closes?

NBA: Toronto Raptors-Media Day John E. Sokolowski-USA TODAY Sports

In his time with Toronto, point guard Kyle Lowry has developed into arguably one of the Top-10 players in the NBA. He’s the living embodiment of the idea that classic box-score stats can’t tell the whole story.

During Lowry’s great October, if you wanted to play the “our stars vs their stars” game, it was easy to see why the Raps were a legitimate title contender.

Comparing Kyle to the #2 player on the other Eastern powers — Boston (Tatum or Horford), Philadelphia (Butler or Simmons), Milwaukee (Bledsoe or Middleton), Indiana (Sabonis or Turner) — the numbers strongly suggested that KLOE-Kyle was better than any of them.

Hell, you could even make a case, especially based on how Lowry played against the Warriors in two early-season games, that if Kawhi Leonard could play Durant to a stand-still, then Lowry could do the same to Steph Curry. It was a long-shot, but Toronto winning the title seemed... possible.

None of that seems possible anymore. Unfortunately, for the Toronto Raptors, now is all that matters. Right now, Kyle Lowry as your second best player says you’re probably not getting past round two.

Since starting the year hot in October, Lowry has averaged 13.1 points and 8.8 assists on a 38.1/30.0/87.4 shooting split. All of those, save the assists, are well below the standard he’s set over his previous four All-Star campaigns, as well as being below his career averages.

Prefer an all-in-one stat? Assuming Kyle plays in 80% of the Raps remaining games, he’s on pace for 2.6 Value Over Replacement Player. That’d be his lowest VORP since 2011-2012, back when he was a Houston Rocket (and, not even the best VORP he’d have put up as a Rocket).

In his recent piece on the All-Star rosters, ESPN’S Zach Lowe had this to say about Lowry.

Lowry has had the strangest season of any candidate. He came out on fire, and then scored in single digits in four consecutive games before missing almost a month with back issues. He has been weirdly passive since, and really all season with Leonard on the floor. His 3-pointer has deserted him. He is averaging just 14 points per game.

He went on to add:

Lowry is going out of his way to defer to Leonard, to the point that you wonder if he is following some organizational fiat or throwing a mini-tantrum — or both.

If you asked me if Kyle was deferring to Leonard to show everyone he accepts that Kawhi is better than DeMar DeRozan, but in doing so also perversely knew, deep in his gut, that that was hurting the Raps, and Lowry’s own chances of winning — I’d say it was all too possible.

Lowry’s an emotional Ferrari. When he’s tuned just right, he purrs. When he’s not — everything seems out of whack. Think back to Lowry’s late-night shooting sessions during the playoffs two years ago. The pressure Lowry was putting on himself wasn’t healthy, Lowry knew it, but he couldn’t do anything about it — it’s how he’s wired. Never has a more emotional Toronto athlete tried so hard to show he’s above being affected by his emotions.

But whether it’s age, injury, or some sort of mental malaise, the fact remains: the Toronto Raptors aren’t going to be good enough to win anything that matters with Lowry playing as he is.

So, after taking the heart from the Toronto Raptors in the DeMar DeRozan trade, does General Manager Masai Ujiri have to explore removing it’s brain as well?

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Of course, we now know, that Masai IS exploring such a deal (allegedly).

Should we be surprised? Not at all. In his time in Toronto, Ujiri has made it clear that his goal is to win a title. Not to come close. Not to compete. But to win.

In that light, Ujiri has to see what everyone else is — that unless Kyle reverts back to KLOE, the Raptors are dead in the water. If the Raps fail to come close to a title the idea that they can keep Leonard seems almost laughable.

The question then is simple: “is the chance that Kyle can find his game, greater than the cost of selling low, and alienating fans if the move fails?”

The other question is: what can you get for Kyle Lowry?

While I understand the Raps trying to make a Lowry-Valanciunas for Gasol-Conley swap - even with some of the other pieces floating around, it doesn’t make a ton of sense for Memphis. (As Josh already broke down, but I’ll toss my two-cents in here too.)

That Grizzlies team would be too good to get the type of draft pick needed to get a star, too expensive to easily add pieces to their “new core” to try a quick rebuild, and not enough future value (taking Valanciunas’ salary into account), that then flipping Lowry would make them better off in the long-term.

Putting Kyle into an Anthony Davis package is the obvious play, but if the Pels are keeping Jrue Holiday, Lowry isn’t needed. And, given the Pels situation, and Lowry’s play, Kyle is probably a B- level asset to them an anyway.

A Lowry for Jrue Holiday deal could make more sense. Holiday and E’Twaun Moore for Lowry, OG Anunoby and Delon Wright works money-wise, but it’s probably not enough for New Orleans. The Pels would want Pascal Siakam, instead of Wright, and at that point it might be too costly for Toronto.

The answer could still be in Memphis though. Just with a smaller deal.

Conley is a player I used to confuse for Lowry back in their early days. It my defense, it makes sense. Both were drafted by the Grizz, both are under-sized but feisty floor-generals. Both have carved out heart-warming NBA bro-mances, and both bring a heck of a lot more to the table than the numbers seem to show.

Right now Conley is averaging 20.3/6.3 on .435/.359/.847 shooting. Now, there is no doubt that when healthy Lowry is better than Conley (again shout-out to Kern). Those Conley splits are barely an improvement on Lowry’s average, but, we’re not talking about even average Lowry here.

Conley’s also a very good defensive point-guard who has been a master at executing the Grit and Grind system. He’s never had a chance to play on a team that could be considered an even-money bet to make an NBA final. He’s never played with much in the way of offensive teammates except for Marc Gasol. It’s wholly possible that there is a better version of Conley inside there, waiting to ball-out for the chance to go deeper than ever before.

A deal of Conley and either JaMychal Green or Garrett Temple for Lowry and Anunoby works.

It might also be enough for both teams (with perhaps a heavily-protected pick added in). The Grizz would get out of an extra $30 million of Conley’s contract, and get Anunoby — who despite his struggles this season still has shine. OG is way cheaper than Valanciunas, and, given the move to wings, probably way more valuable too.

In Memphis, OG could become more of an instigator of the offense, giving him a chance to focus full-time on developing the Kawhi-lite skill-set he was teasing in Indiana.

The Grizz could hope that Lowry puts the chip back on his shoulder, finishes strong, and as an expiring deal next year, is enough to net them some interesting goodies. If Kyle finds KLOE, then the Grizz could easily have the most valuable rental player in the league — if a run at an 8th playoff seed isn’t more appealing to them.

Up North, Conley’s scoring punch would be a huge boost for the Raptors who have been basically average on the offensive end for almost two months. Conley could give Leonard a chance to breath easier in tight games. With Toronto using Serge Ibaka more and more like the Grizz have Gasol, Conley should be able to replicate Lowry’s magic with the Congolese big-man.

Either Temple or Green (I like Green better, but could be convinced), give the Raptors the 3-and-D presence they’d hoped to get from Anunoby. Both are willing defenders, and while neither is an elite three-point shooter — Green is at 39.6 % and 36% for his career, Temple is 35% for both — they’d both be better than almost every Raptor not named Danny, Kawhi or Fred.

Conley’s extra year isn’t that big a deal either. In the best case scenario where Toronto makes a deep run, Leonard and Conley get on well, and Leonard decides to stay — it opens the core window for title contention to two years.

If Leonard leaves, then Ujiri has options: if Irving and Butler flee Boston and Philly and a Conley/Siakam/Ibaka trio is better than expected he can ride it. Or, he can take less return for a year and a half of Conley (still a very good PG), or delay the total tear-down by a season and deal an expiring Conley for a theoretical better return. For a better shot at a title, it’s worth the inconvenience to the rebuild.

Of course, there is no guarantee that even if Conley is a clear upgrade on the current iteration of Kyle that the Raps would get past two of Philly, Boston and Milwaukee. Whacking DeRozan and Lowry in back-to-back years could also give Toronto an awful reputation as the biggest mercenaries in the league. That could impact future free agents’ decisions. (That might be less of a factor here than in other markets. It also might give Toronto the unshakable reputation of being a franchise dedicated to winning. That has value too.)

Still, with the window Ujiri pushed open, the Raptors have to be comfortable taking the risk — they may not get this close again for years.

Trading Kyle Lowry might not be the answer, but if the other answer is waiting and hoping it seems obvious which choice Ujiri is going to make.