The 2020s have big things in store for the Yankees

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A new year is upon us, as is a new decade. And, for the first time since the 1980s (and before that the 1910s), the Yankees finished the 2010s without winning a World Series. They also didn’t appear in one for the first time since the 1910s. Let’s hope that changes over the next ten seasons, right?

There were some lean years during the 2010s, particularly the 2013 through 2016 teams, though those clubs still played over .500. I can’t imagine seeing a team like any of those again soon, at least not until the end of this decade when the core hits its mid-to-late thirties. The Yankees are in a much better position, from the top to the bottom of the organization, for lasting success than they were ten years ago. Here’s what we can hope for and look forward to over the next decade:

Forget 28 — Why not World Series title number 30?

Time to act like the stereotypical spoiled Yankees fan, because why not? Winning number 28 would be great, especially this year, but why not think bigger? Multiple championships seem within reach for this core. I’ll dig a little deeper into the exciting young talent the team possesses in a bit.

Similar to the 2009 team, this year’s club has the expectation to win it all after a (relatively speaking) long gap sine the previous one. That team got the job done and won the 2009 World Series over Philadelphia, but that core group didn’t reach the pinnacle again. It’s always a lot to demand a championship — let alone multiple — but the current roster is in better position than the 2009 team for sustained excellence.

A decade of Gerrit Cole

Cole left out the 2020s on his sign.

Chances are that Gerrit Cole will be in pinstripes through at least 2028. His nine year deal does have an opt-out after 2024, but the Yankees have the choice to tack on one more season in 2029 to retain him. He’s only going to opt-out if he pitches well. By then, the Yankees probably will want to retain him and add that extra season. In any case, he’s here for a long time.

The prospect of having the best pitcher in the world to start the decade feels pretty good, wouldn’t you say? He’s 29 years old and will almost certainly remain at the top of his game for at least the next few seasons, but even in his decline phase he should still be quite good.

Similar to how CC Sabathia was the cornerstone of the rotation during the last decade, Cole will offer that same presence in the Bronx for a while.

The core’s prime years and keeping them together

PlayerCurrent AgeFree Agent Age (Year)
Aaron Judge27.730.7 (post-2022)
Gleyber Torres23.028.0 (post-2024)
Giancarlo Stanton30.138.1 (post-2027)
Gary Sánchez27.130.1 (post-2022)
Gio Urshela28.232.2 (post-2023)
Luke Voit28.933.9 (post-2024)
Miguel Andújar 24.828.8 (post-2023)
Aaron Hicks30.237.2 (post-2026)
Clint Frazier25.330.3 (post-2024)
Gerrit Cole29.338.3 (post-2028)
Luis Severino25.929.9 (post-2023)

Everyone listed in the table above may not fit the criteria of a “core” player, but the point is that the Yankees have multitude of guys who are currently in the primes of their careers and will continue to be for the early portion of this decade. That’s promising!

Of course, it also means that the Yankees will need to spend some money to keep the gang together. In particular, paydays for Aaron Judge and Gary Sánchez are coming up soon. Barring something unforeseen, they’ll be under contract with the Yankees for three more seasons before they hit free agency.

Still, the Yankees aren’t going to keep everyone here. Some of these players’ careers could fizzle out before they hit free agency, whereas others could sign elsewhere or get traded. That’s the nature of the business, though the Yankees really should not be in the business of letting superstars go. Guys like Judge need to get paid.

Having a strong core now sets the Bombers up well for this decade, but there’s a shelf life to every big leaguer’s career. So, the Yankees will need to replenish over the years. The good news is that the team seems to be in position to do so. The organization has gotten better at player development and identifying talent.

The team’s farm system got substantially better in the mid-to-late 2010s, and there’s a nice crop of young guys like Deivi García and Clarke Schmidt lingering. Further way is Jasson Dominguez, who I’ll get to shortly. Now, this isn’t quite as good of a system as just a few years ago. That’ll happen when guys like Gleyber Torres graduate. But still, remember how bad things once were in the early-to-mid 2000s? Things are in much better shape now.

It’s not just the farm system that’s promising though. There’s also the front office’s ability to find hidden gems or rebuild a “failed” prospect. The team has identified wonders in Didi Gregorius, Aaron Hicks, Mike Tauchman, Luke Voit, and Gio Urshela (just to name a few). This seems like a true advantage for the front office that could keep the Yankees ahead of the pack.

Records & Milestones

With long careers come milestones — hopefully two things a number of Yankees players achieve during the ’20s. Let’s run down a few that could come.

Home runs are in vogue and the Yankees have no shortage of players who hit them. Giancarlo Stanton has 308 career dingers to his name, and unless he falls off a cliff, there’s a good shot he reaches 500 with the Yankees. Then there’s the other large slugger in the lineup, Aaron Judge, who has 110 homers. How far he gets in pinstripes depends on his sustained success and the organization re-signing him, but there’s no doubt he has potential for a big lifetime total.

Sánchez also has a chance to set some catcher-records. He hit a career-high 34 homers this season; could he top Javy López’s 42 in 2003? Gary certainly seems capable if he could stay healthy. What about career homers? Mike Piazza’s 427 are most for a backstop. Gary’s at 105 through his age-26 season; Piazza had 92 at the same juncture. Still, the odds are slim and it’ll take quite a bit of longevity for Gary to even come close. It’ll also require the Yankees keeping him around once he’s a free agent after 2022.

On the pitching side, Cole is the one to watch. I know wins aren’t a big deal, but he’s at 94 right now and almost certainly will surpass 200 with the Yankees. 250 will be harder: he’d have to average just over 17 wins per year through 2028. On the other hand, 3,000 strikeouts seems within reach. With 1,336 entering this year, he’d need to tally 185 Ks per season to reach that figure.

Jasson Dominguez’s debut

Dominguez is merely 16 years-old, so it’s going to be a while before we see him in pinstripes. In fact, the prime of his career could be in the 2030s, not 2020s. It’s weird to say that.

In any event, provided that Dominguez’s prospect trajectory follows the hype, his debut is going to be a major event this decade. Prospects will break your heart, but all we can do right now is dream on his potential. See you in 2024 or 2025, Jasson.

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4 Comments

  1. DJ Lemeddardhieu

    Yes they do, Derek, and this decade better resemble the 90’s or heads will roll. I’d go into Boone’s office and tell him he has 2 options – 1. Win the World Series 2. You’re fired. There are no excuses anymore. Cole was signed, everybody is healthy, Boone has the best club in baseball. This team should have won at least one ring by now and needs to win multiple rings this decade to make up for the lost 2010’s. I’d lock up all of those kids to long term contracts so they end their careers as Yankees.

    The biggest concern to me are the losses of Romine and Nestor and to a lesser extent Didi and Dellin. Those were key players for us last year and now they’re going to be helping other clubs beat us. And if Cameron isn’t re-signed that’s another key loss. This FO got Cole but hasn’t done anything else. The Mets outfoxed us on Dellin, the Jays outfoxed us on Ryu, Girardi outfoxed us on Didi and the Sox outfoxed us by sitting back and waiting for us to screw up.

    • Finally, a comment that I can get behind. Enough of the rationality and justification of Yankees failures, we need to go back to the “Old man yells at cloud” Yankee fans.

      The reason the 2019 Yankees lost was because they didn’t BUNT enough, and I don’t care how many times he gets caught, Brett Gardner should steal every time he gets on! Furthermore, Luis Cessa needs to be the 8th inning guy in 2020 to separate Britton and Chapman because they’re too left-handed, I once saw him strike Miguel Cabrera out on 3 straight pitches!

    • “The biggest concern to me are the losses of Romine and Nestor and to a lesser extent Didi and Dellin”

      Lol

  2. Wow, Jasson Dominguez looks like a switch hitting Javy Baez.

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