2. Madison Bumgarner
The idea of the Yankees making a deal with the Giants for their talented ace is nothing new. There’s little doubt the two organizations have discussed Bumgarner on multiple occasions, but a deal has never made sense for both teams at the same time. That could change this winter.
The Giants have to face facts. Bumgarner will be a free agent in 2020 and they don’t have talent to be a World Series contender next season. The clock is ticking on their opportunity to trade him and get anything approximating equal value in return.
San Francisco could wait until the trade deadline to move him to a contender desperate for starting pitching, but that’s risky. If Bumgarner misses significant time due to injury as he did this past year it could really depress his trade value. At the very least, the Giants front office owes it to their fans to listen intently to offers this offseason.
If the Yankees are motivated to really fix their rotation, they will consider making a massive offer for Bumgarner. A deal starting with a package built around Justus Sheffield and Clint Frazier might be enough to get a deal done. Those two guys won’t be enough on their own, but they are enough to spark a meaningful conversation between both teams.