Yankees should reunite with this old friend on cheap free agent deal

The Yankees should reunite with old friend Ian Kennedy on a cheap free agent deal after a rough 2020 season.

All things considered (kind of crazy, we know), the Yankees’ Ian Kennedy–Phil Hughes–Joba Chamberlain triumvirate worked out … relatively fine, as far as pitching prospects go.

Did any of the three live up to their tremendous potential, anchoring the Yanks’ rotation for years to come? Well, no. But in a notoriously impossible-to-predict field, the team ended up with a sterling ’07 postseason from Joba, a solid if strange ’08 campaign, and a World Series win with both he and Hughes serving as integral pieces of the ‘pen. Hughes was also the team’s best starter throughout an ALCS season in 2010, making the All-Star team.

By far the least any of the trio had to offer the team came from Kennedy. Amazing in a 2007 cameo (1-0, 1.89 ERA in three starts), IPK was the worst of the worst when the team handed over the rotation reins to the kids in 2008 (a cautionary tale for the 2020-21 offseason, by the way), posting an abhorrent 8.17 mark in nine starts before injuries took their toll.

But since leaving the Yankees, Kennedy has done it all. He nearly won the Cy Young in 2011 in Arizona, wrapping up with a 21-4 record. And though he’s bounced around a bit as a solid swingman in the years since, he reestablished himself as a dynamic bullpen weapon in Kansas City in 2019.

Eventually, Kennedy’s ERA on the year settled at 3.41, as he worked high-leverage innings for a disappointing Royals team, seemingly turning himself into a bonafide trade piece overnight.

Somehow, though, KC decided to sit on Kennedy despite jettisoning just about everyone else at that particular deadline, and he’s now available for cash alone in ’20-’21, his deal officially expired.

He’s also, coincidentally, coming off the worst stretch of his career since 2008, finishing the shortened season with a 9.00 ERA in 14.0 innings pitched (15 whiffs! Eh?).

Brian Cashman should spend big this offseason to maximize the Yankees’ window (though we already know he won’t). So if dumpster diving’s the name of the game, why not pick up an effective name we’re familiar with who’s likely at his lowest-ever value?

Chamberlain is long-retired, as is Hughes, who’s likely known more for being extremely entertaining while ripping high-dollar baseball cards on YouTube at this point than his post-’09 exploits. If Kennedy’s going to be the last one standing anyway, he might as well come home.

Yankees: 3 players who’ve likely played their last game in New York

These three Yankees (and, OK, fine, many others) have probably played their final games in New York following the 2020 MLB season.