Lance Lynn, Chicago White Sox
Lance Lynn makes $19 million this season with this Chicago White Sox, which should be entirely disqualifying in this conversation before we even pass "Go." In order to absorb his remaining salary without crossing the top luxury tax threshold, the Yankees would have to clear ~$7.5 million from their payroll, which already sits $1.1 million above the top number. That would be Wandy Peralta, Isiah Kiner-Falefa and Luis Severino.
In case you need further justification to avoid a return engagement with Lynn, he's remained remarkably hittable all year long, despite still-sterling strikeout numbers and whiff rates. Lynn's 139 Ks in 115 innings are impressive, and his ERA/FIP disparity indicate his best starts could still be ahead of him.
That ERA and FIP are 6.18 and 5.28, though. That is a bad starting pitcher in a season-long slump, by any measure.
The Yankees already tried to swipe Lynn and make him over during a mid-career stumble once back in 2018. They added him at a discount at the deadline after he'd signed late and posted a 5.10 ERA in 102.1 innings with Minnesota. That summer, he posted a 4.14 ERA in New York with a sterling and very unlucky 2.17 FIP ... but by the time October rolled around, he was deemphasized and misused, entering in relief against the Red Sox before bolting in free agency.
"That was Larry Rothschild! This is Matt Blake! The strikeout numbers are there now! They weren't before!" Enough. Enough. Don't clear $7+ million in salary to absorb Lance Lynn's contract. Don't. Not the time. Not the place. Shouldn't have to preach that, but we will just in case.