3 veteran free agent fits that would greatly help Yankees clubhouse morale

2. Jon Lester

It depends how much he costs, but Jon Lester could be a great addition for the Yankees.

Nobody knows what’s next for Jon Lester. He had his player option declined by the Chicago Cubs and he’s a free agent again for the first time since 2014. His time with the Cubbies wasn’t overly impressive, but he helped deliver that elusive World Series, and that’s all that matters. The man has three rings and, while he’s fallen off the map pretty hard over the last two seasons, he could still be a valuable back-end rotation piece for the right price.

The Yankees need a left-hander, veteran, and insurance policy for their cast of starters, so could Lester be a fit on a cheap one-year deal? The Cubs tried to relieve him of pressure in trading for Jose Quintana and signing Yu Darvish, but Quintana never worked out and Darvish was a late-bloomer, not performing until this past season.

Cashman can clearly communicate to Lester that the Yankees want him as a mentor alongside Gerrit Cole for the young arms (Jordan Montgomery, Deivi Garcia, Clarke Schmidt) and will help him work to get back to his innings-eating self, which hasn’t been the case since 2016. Perhaps a bit of a rediscovery could see the 36-year-old regain some value since it’s now the lowest it’s even been … by far.

Lester could be intrigued to take on a different role while also playing for a bonafide World Series contender. And what better way to stick it to the Red Sox for trading him and lowballing him with contract offers? Sign us up for the southpaw getting ~25 starts in the back of the Yanks rotation, which could prove to be an invaluable addition come October…