Ranking players Yankees should consider signing to contract extensions

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.