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.

4. Jordan Montgomery

In what’s shaping up to be a career year for Jordan Montgomery, the Yankees might actually be smarter to wait this one out, but why not at least test the waters? Monty is a homegrown Yankee, and there’s always sentimental value when that’s the case.

Then again, he’s a client of Scott Boras, so … money will likely be the No. 1 driving factor in retaining him. Does Boras want to play out the next 1.5 years, though, instead of getting his client deserved money right now ahead of his age-30 season?

Montgomery is under club control through 2023, so, like Sevy, there isn’t a rush here, but he’s making just $6 million in 2022 and will be due for a considerable raise next year assuming he continues on this amazing trajectory (3-1, 2.72 ERA, 3.54 FIP, 0.95 WHIP and 56 strikeouts in 13 starts).

For some players, security is crucial, and with the left-hander already undergoing Tommy John surgery back in 2018, he may not be open to rolling the dice in 2023 since there’s no telling what this roster might look like a year from now.

In reality, Monty will need 2022 and 2023 to be massive successes if he wants to secure the bag, because right now his career high in innings pitched is 157.1 and he doesn’t exactly dazzle with any of his pitches — he just goes out there and works. Often times, those aren’t the kinds of guys who get the most money when the payday arrives.

3. Jameson Taillon

More. Pitchers. They are the bedrock of any given roster. And now that Jameson Taillon has fully validated the Yankees’ acquisition of him, it’d be best to keep him around for his future prime years after his blistering start in 2022 (8-1, 2.70 ERA, 3.00 FIP, 1.05 WHIP and 60 strikeouts in 13 starts).

Taillon is a free agent after 2022, which makes this more urgent than the last two (duh, it’s why he ranks ahead of them). Truth be told, the Yankees traded for him likely hoping they’d see the results in 2022. He underwent his second Tommy John surgery and beat testicular cancer before arriving in New York, so one can hope the worst is behind the unflappable right-hander.

What the Yankees are accomplishing right now with Taillon among those leading the way, there’s no reason for them to jump ship and go shopping for another starter who either won’t be as good or will require more time for the team to develop or unlock.

Like Severino, the Yankees experienced a sort of growing pain with Taillon in 2021, which pretty much served as his big-league rehab year post-TJ. The money to retain Taillon will be there, too, with Zack Britton, Aroldis Chapman, Joey Gallo, Chad Green and others freeing up over $40 million on the payroll.

All we’re trying to say is that it’d be a waste to have to go back to the drawing board for the rotation if a guy as impactful of Taillon departs after finally proving what he can do on a contender.

1. Aaron Judge

Didn’t see this one coming, did you? Must’ve thought the spot was saved for Aroldis Chapman. We get it.

All jokes aside, Judge has earned AT LEAST an extra $40 million from the Yankees with his play so far in 2022. He’s the leading AL MVP candidate (don’t listen to any of the Jose Ramirez chatter at the moment), as he has the most runs scored (55) and home runs (25) in MLB, all the while playing Gold Glove-caliber defense in center field.

He’s the face of the Yankees and arguably of baseball, depending who you ask. Sorry, but there’s not much more of an explanation needed here. We’re trying our best.

The Yankees did make a fair offer of seven years and $213.5 million before Opening Day, which would’ve made Judge the second-highest paid outfielder in the game behind Mike Trout. Judge rejected it, thought he could make more, and has proven that before our very eyes. The investment here might be tough to swallow, but it’ll be harder to cope with Judge leaving in free agency and putting another team in the World Series discussion (or making a contender that much stronger).

“The Price Went Up,” as Yankees Twitter loves to say. And if they’re right about anything, it’s that. The cost here isn’t the issue, though. This is the New York Yankees we’re talking about — one of the most valuable sports franchises in the world. They can pay for three years of regression with the amount of money Judge rakes in with his overall recognition, merch sales, ad spots, you name it.

This is the most important Yankee to keep in pinstripes. After Judge, the rest of the necessary dominoes fall. But if the Yankees do anything before the year ends, they need to get Judge under contract or convince him a capable roster will continue to be around him by working out deals with a few of the other aforementioned guys on this list.

Imagine if Yankees had traded Gleyber Torres like I asked them to?

We asked the New York Yankees to trade Gleyber Torres prior to 2022 for, like, Frankie Montas or something, and I am SO dumb.