Yankees Potential Trade Target: Jesse Winker

The New York Yankees have more pressing needs than corner outfielders. They badly need a shortstop, they could use a capable center fielder and a first baseman, and they also should bring in at least two quality starters. But if they have a chance to trade for Cincinnati Reds’ slugger Jesse Winker, they should by all means consider making a move, even if the fit is less than perfect.

Winker has blossomed, in the last couple of years, into one of the best left-handed hitters in baseball (something the Yankees would surely find attractive), capable of combining contact ability with impressive power and an excellent eye at the plate. He’s a triple threat in that sense, and that’s why his wRC+ marks in the last two seasons have been 143 and 148.

After hitting almost two groundballs for every fly ball in 2019 (1.96 GB/FB), Winker has worked on his swing to increase his launch angle and improved that number to 1.67 in 2020 and 1.26 in 2021, his best season to date. He also started to hit the ball with more authority in 2020, and has finished with at least an 11 percent barrel rate and a 46 percent hard-hit rate in each of the least two campaigns.

Winker had a full-on career year in 2021. He slashed .305/.394/.556 with a 148 wRC+, a 10.9 percent walk rate and an excellent strikeout rate for a slugger at 15.5 percent. He hit 24 home runs, 77 runs, and 71 RBI, but he played only 110 games: one has to think that, with at least 150 games, we would have easily eclipsed the 30-homer mark.

Winker is limited to the corners on defense, and he isn’t particularly good there. The Yankees have several stellar corner outfield-type hitters. However, every manager would be happy with a hitter of Winker’s caliber, and with his price going up in arbitration for the next two seasons, the highly cost-conscious Reds may be willing to talk business. If he had three or four arbitration years left, one would think there would be no chance of Winker getting traded. But two years from free agency can be a sweet spot for Brian Cashman and the Yankees in terms of trading prospects for players. That’s the point at which the prices become less exorbitant, bringing Winker into New York’s range.

The Yankees do have Aaron Judge, Giancarlo Stanton, and Joey Gallo capable of playing the corners, and Aaron Hicks for center field. However, bringing in Winker could mean they have some quality depth in case something happens to the injury-prone Stanton and Hicks. It could also mean that Gallo could play a lot of center. Winker could also be insurance for 2023, since the Yankees don’t know, at this point in time, if they will be able to count on Judge and Gallo being in the Bronx beyond 2022. Again, it’s not a perfect fit, but Winker would bring a lot to this roster for the next two seasons.

Now, Winker is very, very good, at least as a hitter, so the Reds would still probably ask for a solid return even if he’s nearing free agency. The Yankees could look to solve multiple problems with one deal, asking the Reds for one of Tyler Mahle or Luis Castillo, or perhaps even Sonny Gray. That would likely mean lead to Cincinnati asking for one of the Yankees’ top three prospects in return, making any such deal a long shot.

A more plausible idea would be the Yankees asking the Reds to package utility infielder Kyle Farmer with Winker. The Yankees have been tied to “stopgap” shortstops all winter, and Farmer would make for a much more attractive option than Andrelton Simmons, who recently came off the board. Farmer ran a passable .263/.316/.416 line in 483 at-bats last year, and ranked in the 90th percentile in Statcast’s Outs Above Average. If the Yankees don’t sign a top-tier shortstop, Farmer could be a better bridge to Anthony Volpe/Oswald Peraza than any of the available stopgap options on the free agent market.

Whether he comes alone or packaged with another piece, Jesse Winker should be a very good addition for the Yankees’ lineup. It would be absolutely perfect fit if he could play some center fielder, but there are always ways to work with such a talented bat. If Cashman can find a reasonable prospect price, he should absolutely consider deepening the Yankee lineup with this lefty swinger.