Tom Szczerbowski-USA TODAY Sport

When Masai Ujiri took over as general manager of the Toronto Raptors, you sort of knew what to expect. Ujiri was going to tear it down, get rid of salary and start the rebuilding process.

Typically, that process necessitates the loss of current assets and games, all for the betterment of the future.

That sort of thing tends to happen naturally when a GM dumps his two most expensive players, like Ujiri did when he traded Andrea Bargnani and Rudy Gay.

So far, though, the opposite has taken place.

Since dealing Gay, the Raptors have been on fire to the tune of a 17-9 record. In that time, DeMar DeRozan has cemented himself as one of the most productive shooting guards in the entire league instead of a clunky fit on a bad salary. Head coach Dwane Casey now looks like a solid motivator and tactician instead of a lame duck. Winning does make everything look a little better, right?

That holds true for point guard Kyle Lowry as well. Lowry has always had the talent, but only now has he truly been able to piece everything together, as teammate Patrick Patterson described to Ryan Wolstat of the Toronto Sun:

I've known Kyle since my rookie year in Houston. That's what I expect from him every night. I know what he’s capable of, I know what he can do. He’s a great facilitator, he's an even better scorer. He understands the game and what he needs to do. He's a workhorse out there, doing all the things to make us win a game and put us in position to win a game. I would love it if he's an all-star. I feel like personally he should make it.

Whether Lowry's best season of his career is a result of being on a contract year or a product of finally being trusted to handle playmaking duties on his own, he's doing and saying all the right things now. He's played arguably the biggest role in Toronto's success so far this season, save for maybe DeRozan.

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That all puts Ujiri in a pretty difficult spot. If the playoffs began today, Toronto would be hosting a first-round playoff series for just the second time in franchise history. That's a big deal, and as the Memphis Grizzlies showed last year, you never know when a few injuries will break your way.

With that in mind, can Ujiri hang on to Lowry and press pause on the rebuild?

Trade rumble: Sense around league remains Toronto more likely to trade Kyle Lowry than keep him to prevent losing asset for nothing. But ... — Marc Stein (@ESPNSteinLine) January 27, 2014

Issue here hasn't changed: No team out there willing YET to meet Raps' asking price for PG who, nice as he's playin, can bolt in free agency — Marc Stein (@ESPNSteinLine) January 27, 2014

While there's certainly a risk that Ujiri will miss the chance to sell high on an expiring asset, it's one that is worth taking for a few different reasons.

The first is that there's a good chance Lowry will come at a discount this offseason. There are only a handful of teams in the league that need a starting point guard, and that's before factoring in the incoming draft prospects or other free agents, and which teams will have cap space to burn.

Lowry will undoubtedly want to start wherever he signs, which will narrow down the field quite a bit. The chances this turns into a bidding war with multiple teams seems relatively slim, as it stands right now.

Even if it does, though, Ujiri can feel comfortable overpaying his 27-year-old guard, because he has a history of turning lemons into lemonade.

When Ujiri was the GM of the Denver Nuggets, he executed a similar plan with Nene and Arron Afflalo.

Nene was re-signed to a huge five-year deal worth $65 million in free agency, then was traded a little more than three months later. Afflalo, meanwhile, was re-signed to a five-year deal worth $43 million, then was traded in less than a year.

Point being, Ujiri can trust in his ability to flip long-term players for valuable assets. It's what he does best.

There's also the chance that Ujiri could negotiate a sign-and-trade deal for Lowry this offseason. If Lowry decides he wants to play for a contender that runs out of the cap space needed to sign him (like the Miami Heat, for example), then Ujiri can receive assets back that way.

So while the trade deadline is approaching ever so swiftly, it doesn't necessarily mean that this will be the last opportunity Ujiri has to move Lowry.

Given that he's playing at an All-Star level right now, maybe it's not out of the question that Toronto will keep Lowry paired with DeRozan long term and find ways to build around a young core that includes Jonas Valanciunas in the middle.

After all, Ujiri will have other assets at his disposal. Toronto owns all its first-round picks, and thanks to the Bargnani deal, it'll have the lesser of the New York Knicks' and Denver Nuggets' first-round choice in 2016.

There will be cap space on the way as well, particularly for the much-anticipated 2015 offseason. As it stands right now, the Raptors have just $22.6 million on the books for the 2015-16 season. If you add a deal in the range of $8-10 million for Lowry to that total, that still leaves plenty of room for Toronto to go after a max player.

Even if Lowry isn't viewed as a piece for the future, it could be incredibly damaging to move him right now. It's more about the message it sends to the young members of the core, the coaching staff and the fans than anything else. Greivis Vasquez is a capable backup, sure, but Lowry has earned his keep and deserves the chance to see this season through. Teams don't typically sell when they're near the top of the standings.

Basketball is a business, but trading Lowry now seems a little emotionally reckless. It's been a long time since the vibes in Toronto were this positive, and Ujiri has to be able to recognize that there's value in establishing a winning culture at this stage.

At this particular point, it just seems like there's too much to lose by dealing Lowry right now. We've seen Ujiri re-sign and then flip players in the past, and here's guessing that's what he chooses to do again.