Caleb Martin, Miami Heat
Over the last two seasons, Caleb Martin has emerged as an absolute difference-maker for the Miami Heat off the bench. Looking back, after the injury to Tyler Herro, the Heat likely wouldn't make the NBA Finals without the contributions of Martin in the Eastern Conference Finals against the Boston Celtics. However, retaining him beyond this season could prove to be difficult for the Heat who have their own financial issues heading into the future.
If the Heat intends on keeping the core of Herro, Bam Adebayo, Jimmy Butler, and Terry Rozier together, and they have any hopes of improving the roster around them, Martin isn't likely to be re-signed. Especially considering that Martin is going to be in line for some big contract offers on the open market of free agency.
Unless the Heat's front office is able to pull a rabbit out of their hats heading into the summer, Martin is likely going to be one of those players the Heat isn't able to keep around. In their most recent reclamation project, Martin is about to cash in heading into free agency. With the way he's played over the last two years, he's likely entering his final postseason run with the Heat.