I have to imagine that trading a player of Bryant's caliber is an as-is sorta situation, you take on the risk when you make the trade. It's too significant a move for the Cubs to make for 2020 to make the return at all contingent on something that comes later. Speaking of trading Bryant, let's connect some dots: - Rosenthal says "[Cubs] officials are telling representatives of even low-budget free agents that they need to clear money before engaging in serious negotiations." - Multiple articles lightly speculating the Braves might try for Bryant, and lets toss in Rogers' guesswork too - The mention that the Cubs are bringing an army of people to the winter meetings, and their comments about shaking up the roster So if they have to cut payroll relative to last season(instead of merely staying flat), then trading Bryant does become more of a realistic means of trying to improve, because there's not many other means of freeing up significant salary unless you can find a taker for Heyward or Chatwood(questionable at best). If that happens 1) I will probably pass out from anger at Tom Ricketts and 2) the Braves do really make the most sense as a team by far. They have MLB ready quality that they aren't necessarily reliant on(to various degrees Fried, Newcomb, Wright, Wilson, Touki, Pache, and Waters all help the Cubs in 2020), a hole at 3B, and motivation to make a big splash.