The Toronto Raptors were supposed to be sellers at the trade deadline. That was the prevailing logic on where the franchise would be in February as it entered the season still reckoning with the departure of Kawhi Leonard while Kyle Lowry, Marc Gasol, and Serge Ibaka each played on expiring contracts. The idea that Toronto would consider selling off pieces of its reigning championship core was based on a reasonable assumption: the team would take a sizable step back without Leonard and start planning around its future, not its present.

The Raptors just so happened to prove every part of that wrong. Through 50 games, Toronto is 36-14 overall, the exact same record it had at this point last season with Leonard. As it clings to the No. 2 seed in the Eastern Conference, it’s becoming clear the Raptors’ days as a contender are far from finished.

There are so many reasons for Toronto’s success this season. Credit Nick Nurse for being arguably the best coach in the NBA. Credit Pascal Siakam for taking another leap without Leonard, this one perhaps making him a top-10 player in the entire league. Credit the Raptors’ unmatched ability to both scout and develop, with Terence Davis and Chris Boucher joining Fred VanVleet as former undrafted free agents who have made a big impact on winning. Credit Lowry for another All-Star season after signing a one-year extension just before opening night.

At this point, the Milwaukee Bucks are the only team clearly ahead of the Raptors in the Eastern Conference pecking order. The Bucks are the same team Toronto took out in last year’s conference finals, even after falling down 0-2 to start the series. Of course, having Leonard changed everything.

Toronto now enters the trade deadline in a fascinating position: should they make another bold move for a run at the Finals, or hold onto their pieces and prioritize the future? Let’s consider their options.

The Raptors could make a bold trade to win-now

If the Raptors think the Bucks are vulnerable in the postseason, team president Masai Ujiri could put together a package of young players to try to bolster the roster for the stretch run. One name jumps out more than any other: New Orleans Pelicans guard Jrue Holiday.

The 29-year-old Holiday would be a fascinating fit. The 6’4 guard can play on- or off-the-ball and has long been known as one of the league’s better two-way players. He could slot in next to Kyle Lowry in the backcourt and give the team two tough, veteran guards who can create their own shot, facilitate, and knock down an open jumper on offense while maintaining what is currently the league’s No. 2 overall defense.

A trade that would send Ibaka and OG Anunoby to New Orleans for Holiday checks out:

There aren’t many other paths to a Holiday deal for Toronto. The Raptors could try to tie in a third team in the trade and send out Norman Powell instead of Anunoby, with Ibaka going to a different location. While it sounds good in theory, it’s going to be difficult. Adding in their first round pick with Anunoby is likely the only way to get New Orleans to bite for Holiday.

The Raptors didn’t need a first round pick to find VanVleet or Davis. It feels like Toronto would be willing to part with their pick for a proven rotation piece on the wing or in the backcourt, but their options for matching incoming salaries are limited. This essentially comes down to whether they want to add Anunoby to a deal.

It would be a heavy, heavy price to pay and leave the Raptors without a a big, defensive-oriented wing in the playoffs. Perhaps Davis could fill that role, or Holiday could slide up a position. While Toronto likely wants to do whatever it can to hold onto Anunoby, Holiday is the type of player that could get them to commit to the deal.

The Raptors could wait for 2021 for their move

It’s no secret that the Raptors have big plans for the summer of 2021. That’s when a stacked free agent class, headlined by reigning MVP Giannis Antetokounmpo, hits the market. There have already been widespread rumors tying the Raptors to Antetokounmpo. Ujiri landed a superstar once before by trading for Leonard, and he wants to do it again, this time in free agency.

To keep their options open for 2021, Toronto has to make sure it doesn’t take on salary that extends beyond next season. Right now, only Siakam is on the books for the 2021-2022 season, though Powell has a player option for $11.6 million that season, and the next deals for Anunoby and Davis would be lined up. It’s another factor that makes finding a deal for Toronto even more difficult.

The Raptors might also just want to hold onto Anunoby. He has a case to be their third best player this year. At 6’7, 230 pounds with a 7’2 wingspan, Anunoby has made strides as an outside shooter (36.5 percent from three-point range on 3.5 attempts per game) while doubling as the team’s go-to wing stopper. Only 22 years old, there’s an easy case to be made Toronto should keep him and make him a focal point of the team’s future.

The Raptors protected Anunoby when they made their trade for Leonard. Would they really part with him now after such an impressive season? Without a clear option to fill his role, Toronto might be better off passing on a big move to keep Anunoby.

The Raptors have been bold in the past. Will they do it again?

Ujiri isn’t afraid to make an all-in move, that’s for sure. He made the biggest NBA trade of the decade in dealing DeMar DeRozan and Jakob Poeltl for Leonard and Danny Green. He also made a big trade in 2017 — acquiring Ibaka for Terrence Ross — and in 2019, when he acquired Gasol for Delon Wright and Jonas Valanciunas.

The Raptors are very good. They were also very good last year, and it didn’t stop them from trading two rotation pieces for Gasol. That move was the final piece for what turned out to be a championship run no one saw coming.

Holiday could fit Toronto’s present and future: he’s under contract through next season, then has a player option for 2021-2022. It’s possible Toronto could trade for him while still maintaining their flexibility to go after Giannis. Of course, that would likely mean parting with Anunoby.

The Raptors are again in position to make a surprising run in the Eastern Conference. Maybe they can do it without a bold move at the trade deadline, but the Bucks are going to be the clear favorite in any matchup. The ball is in Ujiri’s court. At this point, Toronto fans can trust him to make the right decision whatever he choses to do.