The Yankees acquired J.A. Happ from the Blue Jays at the 2018 trade deadline, hoping he would give the rotation a much needed boost ahead of a promising playoff run. Happ started 11 games for the Yankees in 2018, exceeding expectations by posting 7-0 record and 2.69 ERA, thus being rewarded a 2yr contract after the season. Unfortunately the 36 year old veteran couldn’t replicate that success in 2019, finishing with a 4.91 ERA across 30 starts, and was subsequently relegated to bullpen duties in October. The most concerning part of Happ’s 2019 season was that he was never able to string together a stretch of consistent outings, making it hard for the Yankees to know what they would be getting every 5th day.

With 1yr left on his contract and now 37, it’s unclear what Happ’s future will look like in 2020. Cashman has already made it widely known that he’ll be aggressively trying to add at least 1 new arm, which we all expect will happen. With starters Jordan Montgomery, Domingo Herman, and Deivi Garcia all on the 40-man roster, the Yankees could be looking to trade the veteran lefty. While his value is currently low, there are a few teams that could be potential suitors for J.A. Happ’s services.
Seattle Mariners
Brian Cashman and Mariners GM Jerry Dipoto have been frequent trade partners, with names like Edwin Encarnacion, James Paxton, and Adam Warren all swapping teams in the past 2 seasons. The Mariners are in the midst of a full on rebuild and traded away several good players with bad contracts last year (Robinson Cano, Encarnacion, etc.), so I’d imagine they would want to shed another bad contract in exchange for Happ. One player that fits the mold is Dee Gordon, the 31yr old second baseman who is set to receive $14 million each of the next 2 seasons. By trading Gordon for Happ, the Mariners would add an extra $3 million to their 2020 payroll, but ultimately save $11 million in 2021. The Yankees would gladly take on Gordan’s contract, as he would slide in as the everyday 2nd baseman, allowing Gleyber to move over to SS and fill the void left by Didi Gregorious.
Philadelphia Phillies
After signing Bryce Harper last off-season, the Phillies finished 2019 with a .500 record, good for 3rd place in the NL East and well short of making the playoffs. Needing to add to their rotation heading into 2020, could a reunion with J.A. Happ (who began his career with the Phillies) be a viable option? It would be a relatively low risk/high reward move for GM Matt Klentak, with the asking price likely being 1 top 30 prospect or 2 low level prospects. Happ would add value to the Phillies as a 5th starter, a left handed arm in a righty dominated rotation, and serve as another veteran presence alongside Jake Arrieta to mentor youngsters Aaron Nola, Zach Eflin, and Vince Velasquez.
Chicago White Sox
The White Sox have already made the biggest splash this off-season, signing free-agent catcher Yasmini Grandel to a 4yr deal. In 2019, the White Sox had a -124 run differential and a collective ERA of 4.90, both ranking among the 10 worst in the league, so fixing their pitching is a big area of focus heading into 2020. While they have an ace in Lucas Giolito, they lack both depth and experience after that, with none of the starters on their current 40-man roster being older than 28. The young core could very much benefit from having Happ’s veteran presence both in the locker room and on the mound, as there are several players in the farm system likely to get meaningful playing time in the majors this season. Realistically the White Sox are still a year away from being true contenders, so trading for Happ with only 1 year of control left might be a long shot. Nonetheless, with no standout team in the AL Central, the Sox could make one or two additional moves and very well be in the mix for a divisional title in 2020.