Yankees: 3 struggling pitchers NYY could bet on at trade deadline

2. Jon Lester

The 37-year-old veteran is well past his prime, but this aging southpaw could still be a valuable asset to a young New York team. In Lester’s last two seasons, he posted a 4.64 ERA, and his fastball velocity has declined every year since 2016. Last year, it topped out at 89.2 mph. His current ERA in two games is an unimpressive 4.09, and did I already mention he’s 37?

So what if he’s a little…mature? Lester still knows the AL East like the back of his left hand, having spent the first stretch of his career with the Boston Red Sox. The five-time All-Star and three-time World Series champion brings experience like no other, and putting him in the rotation even for just a few months would let others mooch off his wisdom.

In the 2020 shortened season, the veteran yielded 64 hits in 61 innings, striking out 42 batters along with walking 17. Though obviously not the pitcher he used to be, Lester’s presence could still be strongly felt in the Yankees rotation. New York should seriously consider bringing in Lester to stabilize the backend of their rotation, similar to how New York used CC Sabathia in short stints at the end of his career.

The Yankees believed that Gerrit Cole was their missing piece to a World Series championship team, but that wasn’t the case in 2020. A trade for Lester would be a win-win: Lester, on the back end of his career, will want to go to a World Series-contending team in 2021, and the Yankees will need his veteran experience to get there.