Yankees: Will they try to trade J.A. Happ this offseason?

Will the Yankees try to trade J.A. Happ this offseason? If Brian Cashman can pull it off and dump his contract it would save the organization more money to pursue free agent ace, Gerrit Cole.

After the Yankees re-signed Happ last offseason to a two-year, $34M contract with a vesting option for 2021 he really struggled in the first year of his deal. In 31 games the left-hander went 12-8 with a 4.91 ERA and 140 K’s in 161.1 IP. Opponents hit .258 against him and he gave up a career-high 34 home runs.

Throughout last season Happ looked like a pitcher who’s best days were clearly behind him and nothing like the All-Star he was with the Blue Jays and Yanks during the 2018 season. Even though he finished the season strong with a 1.35 ERA in September it’s hard to be overly optimistic that the 37-year-old will rebound with a stronger campaign in 2020.

If the 2020 season started today Happ would likely be a part of New York’s rotation, but we’re still months away from Opening Day and if there’s anyone in that group who could be the odd man out this offseason it would be him. Nobody else in the Yanks projected rotation for next season is going anywhere and that’s including the returning Jordan Montgomery.

In a perfect world, the Yankees would love to upgrade their starting staff by replacing Happ with Gerrit Cole, the top prize of this years’ free-agent market. However, unless they can find a trade partner for Happ and his contract, which is not going to be easy by any means, the Yanks might not have enough money to go all-in on Cole and offer him whatever he wants.

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Happ is still owed $17M next season and if he reaches 27 starts or 165 innings his contract will vest and he’ll earn another $17M in 2021. There’s no way the Yankees want that contract to vest and if he remains with the club in 2020 it’s doubtful they’ll allow him to reach those marks, but another team might.

According to Joel Sherman of the New York Post, one way they could trade Happ without having to eat a majority of the money owed to him is by attaching another player to him that’s more desirable.

"“One outside executive who believed the Yankees would go for Cole if they could clear salary suggested that the Yankees would try to attach a desirable second piece to Happ and trade him to a starter-hungry team such as the Angels or White Sox, who would not mind the risk of the 2021 option vesting. For example, tie Luis Cessa or a pitching prospect to Happ.”"

There are definitely some teams out there who could use a veteran starter like Happ that can afford to pay him his vesting option but it’s probably going to take more than him and a player of Luis Cessa’s caliber to complete a deal. Including a pitching prospect like Albert Abreu or Nick Nelson in a potential offer instead could make it easier to find a new home for Happ.

Trading away a promising prospect just to get rid of a bad contract could come back to haunt the Yanks but it’s absolutely worth the risk if it helps lead to them landing Cole. After all, that needs to be their top priority this offseason so if they’re still worried about financial restrictions and need to clear more salary to sign him they have to find a way to dump Happ.