The Boston Red Sox, who always have championship expectations, have a conundrum on their hands. Mookie Betts is unquestionably their best player, but he's a free agent after the 2020 season and it doesn't look like he'll sign an extension before then.

 

 

 

Trading him before the season is sensible, but moving your best player doesn't make it look like you're trying to win. So, they should try to straddle both lines and move Betts, while also getting a return that keeps them in the title hunt.