Chicago White Sox
The White Sox rebuild is nearing its completion, and the team is looking to be a contender to win the AL Central in the near future. If prospect Eloy Jimenez makes his way to the big leagues this year and Yoan Moncada begins to play up to his potential the White Sox could be the bounce back team of 2019.
When Eloy comes up it would be good for him to have an experienced and offensively successful outfielder to learn from, so Brantley would be able to help the White Sox on both the mentoring and performance fronts. After spending his entire big league career with the Indians he is very familiar with the AL Central, which is another plus.
The White Sox are rumored to be going after both Bryce Harper and Manny Machado this offseason, so it doesn’t seem like they’ll be spending averse.
If neither Harper or Machado are acquired the team will probably want to wait until next year to make their big free agent signing, when players like Nolan Arenado and Paul Goldschmidt will become available, so the signing of a player like Brantley who make come a little cheaper is fairly likely.