Kyle Lowry is perhaps the most accomplished player in Toronto Raptors history. The six-time All-Star was, aside from Kawhi Leonard, the most important part of the team's 2019 championship run, but with Lowry now 34 years old and the Raptors below .500, it might be time for the two sides to go their separate ways. According to Bleacher Report's Jake Fischer, "There is a portion of Raptors personnel, league sources said, that believes the franchise should bid its beloved All-Star farewell and begin Toronto's next chapter in earnest."

On paper, such a move would make sense. The incentive to keep a franchise icon in place isn't as strong with the Raptors playing in Tampa Bay rather than Toronto this season. Pascal Siakam and Fred VanVleet are only 26. OG Anunoby is 23. The three of them could form the core of a long-term winner, but only if the rest of the roster is managed properly. Toronto could have max cap space this offseason, but only if it lets Lowry walk in free agency. Cashing him in now could give the Raptors the assets they'd need to replace him down the line. 

Finding a trade partner would be a somewhat difficult undertaking from a cap perspective. Lowry will earn $30 million this season, and matching such a hefty number during a pandemic season won't be easy. That is especially true given the number of likely suitors that are hard-capped. Of the 29 teams Toronto could possibly deal Lowry to, 17 are dealing with hard caps thanks to their offseason moves. Some of those teams have more than enough room below the line to make a move, but others, like the Los Angeles Clippers and Milwaukee Bucks, are pressed up against the apron as is. That doesn't preclude them from making a deal, but it makes aggregating multiple salaries to reach Lowry's extremely difficult because room needs to be left over to fill out the roster. 

But a player of Lowry's talents will have plenty of suitors. The Clippers, lacking a traditional point guard, would make sense if they could make the money work, though their lack of tradeable first-round picks will also complicate a deal. The Miami Heat are in a similar position. Lowry's hometown team, the Philadelphia 76ers, could use a more traditional point guard, and unlike the Clippers and Heat, they are not hard-capped. 

What Toronto would demand in such a deal remains unclear. In what is shaping up to be a seller's market, Toronto might have the best available player on the board. They should therefore expect to extract a decent price for Lowry in terms of draft assets and young talent, should they decide to move him. The Ringer's Kevin O'Connor reported Monday that they are interested in Andre Drummond. That would suggest a desire to remain competitive with players still in or near their primes.

But the Raptors have clawed their way back into the playoff race after a slow start. They currently hold the No. 9 seed in the Eastern Conference. Should that hold, they would at least have a chance to reach the postseason through the play-in tournament. That's hardly what the Raptors expected after years of contention, but if the goal remains winning at all costs, Lowry is undoubtedly an essential cog in that enterprise. If, however, the Raptors are looking ahead to a future without Lowry, then a deal now makes the most sense for all parties involved.