No. 1: Chris Boucher
The Toronto Raptors have seen a number of their "wins" as a franchise leave town over the last calendar year, be that trading non-lottery gems like Pascal Siakam and OG Anunoby or seeing the undrafted Fred VanVleet walk in free agency last summer. This summer they may move on from another one, big man Chris Boucher.
The undrafted big man has played 356 of his 357 career games with the Raptors, combining a functional outside shot with his shot-blocking and rebounding. He has never played a large role, starting just 23 of those games, but he has been a Toronto fixture and is the last remaining player from their title-winning team.
He is also 31 years old, under contract for $10.8 million next season and not a fit in Toronto's long-term plans. He hasn't been able to develop into a player who either deserves nor can handle a larger role, and it makes more sense for the Raptors to get younger at that position and develop someone behind Jakob Poeltl and Kelly Olynyk.
Boucher is therefore excellent matching salary for the Raptors to use in a trade this summer. Paired with the Raptors' cap space, they could move him to a team looking for frontcourt depth and take back a more expensive player. He also would fit easily into the full MLE, which under the new CBA can be used to trade for players.
If a market doesn't materialize for Boucher the Raptors can hold onto him and look to move him against at the Trade Deadline, but if they are going to be active on the trade market this summer, Boucher seems like the most likely candidate to be included in a deal.