Jayson Tatum – RFA 2021
Calling this a longshot is a criminal understatement. There was already no way Jayson Tatum was getting out of Boston anyway. But factor in the changing of courses the Celtics have had to do over the past year. After being mentioned as possible AD-trade fodder and going from leading a team to sometimes operating as a third option, Tatum should be wearing green for some time.
Now that all that logic is out of the way, this would be a no-brainer the likes of which haven’t been seen since…well, this offseason. Tatum led the Celtics in three-point percentage during the 2017-18 regular season and in scoring through those same playoffs. He raised his scoring output this past season but, understandably, took a step back in the playoffs with Kyrie Irving healthy.
Brandon Ingram – RFA 2020
This is the long shot with the most legs (*crickets*). Brandon Ingram was sent to New Orleans in the package for AD and he has similar odds as Tatum of leaving Boston. If it weren’t for his health concerns there would probably already be more extension talk. Instead, there are persistent rumors that he could still be moved.
That honestly just increases the likelihood he is extended, either by the Pelicans or the team that trades for him. That makes it an off-chance he even reaches free agency but off-chances are what this section is about. A player with his length, scoring ability, and ball handling would be tremendous in Chicago. It would certainly alleviate some of the playmaking burden from Zach.