Cobb, 30, has some durability concerns, as he underwent Tommy John surgery in 2015 and has never thrown more than 179.1 innings in a season. Despite that uncertainty, he’s one of the top starting pitchers on the free-agent market this offseason and is likely to get a multi-year deal with an average annual value well over $10 million per season.
Chicago has been considered the strong favorite to sign Cobb for a long while now since his former manager, Joe Maddon, is now the Cubs’ skipper. Those odds only increased after Maddon brought in former Rays pitching coach Jim Hickey late last month. Cobb even said on MLB Network Radio that “if we moved down the line and were able to have some discussions with them, I’d be very honored to be able to talk with them and hopefully come to a deal.”
The Cubs are in need of a veteran starter with Jon Lackey and Jake Arrieta being free agents this offseason and very little rotation depth likely to come out of their minor-league system. Though Eddie Butler and Mike Montgomery pitched decently as spot starters in 2017 and could fill those types of part-time roles again down the road, the Cubs surely want a couple more established starters behind Jon Lester, Kyle Hendricks, and Jose Quintana heading into next season.
The Yankees have less incentive to add a starting pitcher this offseason, especially one that is due to make as much as Cobb will. Luis Severino, Masahiro Tanaka, and Sonny Gray are already locked into rotation spots, with Jordan Montgomery also a good bet to be part of the rotation in 2018. Guys like Luis Cessa, Chad Green, Domingo German, and Bryan Mitchell are currently considered candidates for the fifth starter spot, and No. 2 prospect Chance Adams is likely to compete for a rotation spot in 2018 after posting an impressive 2.89 ERA and 1.08 WHIP over 21 starts at Triple-A Scranton-Wilkes Barre.