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Tampa Bay Rays
This is probably the most logical and realistic destination. The Cubs and Rays have linked for years, mostly on guys like Chris Archer and Alex Cobb. Cobb is now a free agent and has been connected to the Cubs ever since free agency started, especially now with Jim Hickey in Chicago. Cobb would love to reunite with Maddon and Hickey, where it all began for him. If the Cubs wanted to rekindle these talks again for Chris Archer, then Happ may have to be included. Otherwise, there’s no chance of a deal.
Archer is going to be 30, which isn’t too old for a pitcher, and he’s coming off a 4.6 WAR season, with a 3.40 FIP, right around his career average. What really entices the Cubs is the 11.15 K/9 and just 2.69 BB/9. He doesn’t walk many hitters, and that was a valid concern for the Cubs front office heading into the offseason. Happ is an excellent start to a rebuild, should the Rays go that way this winter.