With the Bucks' championship in the rearview, and the NBA set to return to its regularly scheduled programming in 2021-22, it's time to look ahead to another condensed offseason. With the draft and free agency on deck, here's a look at four teams that have huge decisions to make in the coming days and weeks:

 

Toronto Raptors

To say the Raptors are at an inflection point may not be a strong enough way to characterize their situation after a nightmarish, displaced season that saw them miss the playoffs for the first time in eight years.

To begin with, Kyle Lowry, the greatest player in franchise history and arguably still the best player on the team, is set to become an unrestricted free agent. For the Raptors, deciding whether or not to re-sign the 35-year-old floor general means deciding how quickly they think they can return to contention. Retaining him would mean betting on the present while letting him go would mean shifting focus more to the future. (Though given the ages of the Raptors' non-Lowry core players, they'd still likely be aiming for a competitive window spanning the next three or four years.) They can open up max space simply by letting Lowry's $43-million cap hold come off their books.

Of course, this is just as much Lowry's decision as it is the Raptors'. He's suggested that the chance to win another championship will be the biggest factor in choosing where he signs his next contract. Does he believe he can do so in Toronto? If not, the Raptors can try to sign-and-trade him to bring back something of value rather than lose him for nothing. But going that route would probably have to bring back a real impact player to justify losing Lowry and nuking their potential cap space.

Either way, it's hard to envision a scenario in which the Raptors can be a better team without Lowry than with him next season. Even with a max salary slot available, they likely aren't adding anyone who'll have a bigger impact on winning than Lowry will in 2021-22. Kawhi Leonard isn't walking back through the door.

What the front office needs to decide is whether they can be good enough with Lowry to be worth punting on an opportunity to add an impactful free agent who can be part of their long-term future. Lowry's still excellent, but his defense slipped last year, his advanced numbers cratered, and Toronto was outscored with him on the floor for the first time in his nine-year tenure with the team.

The Raptors' cleanest course of action might be to let Lowry walk and use their No. 4 pick to draft heady guard Jalen Suggs (widely expected to be the best player available at that slot) in the hopes that he can grow into a foundational backcourt piece. Then they can use their cap space to acquire a long-term answer at center, perhaps by signing Richaun Holmes or throwing a big offer sheet at a young RFA like Jarrett Allen, as some reports suggest they're interested in doing.

They have a lot of options with that No. 4 pick. Popular consensus suggests Suggs should be the guy, but the Raptors may take a different view, and their front office has earned the benefit of the doubt when it comes to prospect evaluation. If they aren't enamored with Suggs, perhaps they can trade down. Or maybe there will be an opportunity to trade up and take big man Evan Mobley, who'd fit their roster perfectly whether Lowry's still there or not.

Is there a universe in which they trade the pick outright? Since Leonard's departure, the Raptors' need for a high-end shot-creator has been evident. With Lowry in gentle decline, that role increasingly fell to Fred VanVleet and Pascal Siakam last year, and for all the leaps those guys have made as playmakers - and, in VanVleet’s case, as a pull-up shooter - neither looks the part of primary initiator for a championship-caliber offense. If the Raptors don't believe they can add that type of player in the draft, maybe they can try to use their plum pick in a package featuring a member of the Siakam-VanVleet-Anunoby trio to swing a deal for an established player of that ilk.

There have been rumblings that Siakam is available, though that may be a situation where "available" really means "available for a price that will prove prohibitive for any potential suitor." There's also restricted free agent Gary Trent Jr., an intriguing if fairly one-dimensional sharpshooter who could be a trade chip or a piece of the future puzzle if he's retained on a mid-market deal.

And looming over it all is the continued haziness over the guy ostensibly tasked with making all the aforementioned decisions: lead executive Masai Ujiri, whose expiring contract has been a source of consternation and anxiety among Raptors fans for more than a year. Can you imagine the Raptors saying goodbye to both Lowry and Ujiri - the two tentpoles of by far the greatest era in franchise history - in the same summer?

Oh, and in case things weren't unsettled enough, the team is still operating out of Florida and hasn’t yet received clarity about whether they’ll be playing home games in Toronto next season. Chaotic times for the 2019 champions.

 

Golden State Warriors

Last season's Warriors provided a good illustration of the perils of trying to build along parallel tracks. They found themselves caught between two imperatives: needing to be patient and foster the development of James Wiseman, their raw rookie big man, and needing to do justice to the outrageous age-33 season Steph Curry put together.

Despite some promising flashes from Wiseman, the Warriors were by any objective measure a significantly worse team with him on the floor in 2020-21. His season-ending knee injury in April took the dilemma out of the coaching staff's hands, and Golden State went 14-5 without him the rest of the way. All told, they performed 13.5 points per 100 possessions better with him on the bench.

This offseason, the Warriors once again have to decide how much they value building a bridge to the future, versus using all the materials on hand to construct a present-day roster that can maximize what remains of Curry's prime. They own the seventh and 14th picks in the coming draft, which they can use to inject their aging core with more young talent (preferably with an emphasis on shooting and off-the-dribble creation), or to take the route they avoided with the No. 2 pick last year by dangling one or both as trade chips.