Ranking players Yankees should consider signing to contract extensions

Who would’ve thought?! Though the New York Yankees usually aren’t ones to negotiate extensions with their players during the season (or at any point before they become free agents), perhaps it’s time for an organizational shift.

Cashman seemingly broke that “policy” when signing Luis Severino and Aaron Hicks to arguably two of the worst contracts in franchise history (injuries derailed both, but Hicks’ continued struggles have made his deal particularly bad).

Yankees fans would like to think those two instances were exceptions to the rule, though. And New York hasn’t really faced a soon-to-be free agent exodus like the one that might hit them after the 2022 season. While it may not be particularly debilitating, it still won’t be easy filling multiple key departures.

Why not get ahead of it while you can? When you possess the resources? When the team is playing this well and gives them a reason to want to stay, with the 2021 stink almost fully dissipated?

And it’s not just 2023 the Yankees need to worry about. The 2024 season will see a number of other valuable players hit the open market, so this will be a recurring theme if there’s no effort to retain some top contributors before other teams can swoop in.

One of the guys on this list is undoubtedly prompting the Yankees to do their homework on the contract extension front, but a few others deserve at least exploratory conversations.

Ranking the Yankees players that deserve contract extensions right now

5. Luis Severino

The Yankees tried this one, inking Severino to a four-year, $40 million extension prior to the 2019 season. The result? A total of 18 regular-season innings from 2019-2021 and now a risk that he’ll be exhausted down the stretch in 2022 with an exponentially larger workload.

But there’s good news. Sevy is 4-1 with a 3.27 ERA, 3.72 FIP, 1.06 WHIP and 80 strikeouts in 12 starts (66 innings) as he returns from multiple injuries that severely limited him since the end of the 2018 season.

At the moment, Sevy has a $15 million team option (with a $2.75 million buyout) for the 2023 season, but the Yankees can possibly get ahead of his success (even more so than last time) and get him under contract for his early 30s.

Severino has plenty of baseball left, assuming his body can hold up after Tommy John surgery, and it’d really feel like a loss if the Yankees pick up his option for next year and don’t ensure he’s a Yankee for longer. They already threw away $25+ million with him on the shelf, but that essentially paid for Sevy to get back to where he is now. He’s not yet quite the “ace” many thought he would be, but he’ll need more time after hardly pitching for three years.

Getting him to sign another four-year extension at a similar rate ($10-$13 million per year) would get the Yankees ahead of the market and keep the top-end/middle of their rotation intact for quite a while.