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This could not have been the season the Toronto Raptors had planned.

When Toronto jumped up the draft lottery and selected Scottie Barnes fourth overall last summer it seemed to mark the changing of the guard for the Raptors. Kyle Lowry was on his way out and suddenly an era of rebuilding was on the horizon. The Raptors weren't going to sell low on Pascal Siakam, but trading the 27-year-old former All-Star for younger assets to build around Barnes seemed like an inevitability, right?

Today, the Raptors are 28-23 and have defied all expectations. Siakam is playing the best basketball of his career, Fred VanVleet is heading to his first All-Star Game later this month, and both Barnes and Gary Trent Jr. have outperformed even the most optimistic projections. Toronto is suddenly sitting sixth in the Eastern Conference, having strung together a five-game winning streak.

Now, with the trade deadline just days away, the Raptors are facing some tough decisions.

A Sense of Urgency

The Raptors want to be buyers and it’s not hard to see why. Barnes’ rapid assentation has expedited the timeline and the prospect of a long drawn-out rebuild has evaporated. It’s time to win while this core is together and that may not be very long.

Toronto Raptors Salary Cap Situation

Toronto's financial situation moving forward

VanVleet and Trent both have player options they'll presumably opt-out of following next season, OG Anunoby and Siakam are both expected to hit free agency the season after that, and Barnes should expect to get a significant extension starting in 2025. That either means the Raptors will be shelling out a ton of money for five very good or a lot of change is coming in the next few years.

What Do the Raptors Need?

The Raptors don’t have anyone over 6-foot-9 on their roster and on paper that’s a problem. How are they going to defend Joel Embiid? How are they going to defensive rebound? Right now, it’s been fine, and the Raptors doesn’t seem fazed. They’re willing to give up the size advantage if it means defensive versatility and offensive mismatches to exploit. Essentially, it’s not an issue.

The real problem is the bench where the Raptors rank dead last in reserve scoring, averaging 22.8 points per game off the bench, nearly five points worse than the 29th ranked Milwaukee Bucks. Couple that with the league’s worst 29.6% bench three-point shooting and Toronto is desperate for some floor spacing and ball handling in its second unit.

Assets to Trade

The Raptors have made it clear they won't be breaking up the core this year, meaning Barnes, VanVleet, Siakam, Anunoby, and Trent aren’t going anywhere mid-season.

Goran Dragic is the most likely piece to be moved and the Raptors have reportedly been looking to pair him with a first-round pick for something valuable. Considering the Cleveland Cavaliers just flipped Ricky Rubio's expiring contract, a lottery-protected first-round pick, and two second-rounders to the Indiana Pacers for Caris LeVert and a second-round pick, expect Dragic's value to be similar.

Chris Boucher and his expiring contract could be moved, though he’s been one of few reliable players off the bench of late. Malachi Flynn seems to have fallen out of favor and makes sense as a re-draft candidate elsewhere. After that, Toronto has all of its first-round picks at its disposal along with some other young pieces that could be intriguing to teams.

Tinkering Around the Edges

Considering Toronto is reluctant to break up its core and Raptors president and vice-chairman Masai Ujiri has never traded multiple first-round picks in a deal, the Raptors are unlikely to make any splashy moves at the deadline. While a true center would certainly help, Toronto already has plenty of frontcourt depth, and adding another bench big the caliber of Khem Birch or Precious Achiuwa isn't going to change Toronto’s outlook. A trade for wing or guard depth, however, might.

Svi Mykhailiuk and Yuta Watanabe have both been a disappointment this season and an upgrade over them with a LeVert-caliber player in a Dragic deal would give Toronto the kind of depth it's been lacking.

Big Offseason Awaits

The upcoming deadline is going to be the precursor to what should be a big offseason this summer. The core is untouchable for now, but big changes are always on the horizon in the NBA.

Toronto's track record suggests the Raptors are going to try to maintain flexibility until the perfect move arises. Barnes has expedited the timeline on this core and when the summer hits, the Raptors may be one big move away from being right back in championship contention.

Further Reading

Chemistry is key as Raptors head into trade deadline week

Pascal Siakam shows he deserves a spot in the All-Star Game in victory over Hawks

Fred VanVleet thinks it'll be hard to keep Pascal Siakam out of the All-Star Game