The Yankees must extend both Aaron Judge and Joey Gallo

Sam Navarro-USA TODAY Sports

On February 9, 2020, the Los Angeles Dodgers had a veritable superteam. Having won 106 games the year prior, they were returning a lineup that had eight players who posted an OPS+ over 108, led by reigning MVP Cody Bellinger, to go along with a pitching staff headlined by Clayton Kershaw and Walker Buehler. Had they decided to bring back the 2019 squad unchanged for 2020, nobody would have batted an eye.

Instead, on February 10, 2020, they traded Alex Verdugo, Jeter Downs, and Connor Wong to the Boston Red Sox for Mookie Betts and David Price, finalizing a trade that had been initially agreed to the week prior but had fallen apart due to medicals. By taking on Price’s contract and parting with a high-level prospect, the Dodgers were able to add one of the game’s most electric players to their lineup, who had multiple Gold Gloves to his name. As good as the outfield of Joc Pederson, A.J. Pollock, and Cody Bellinger had been, Betts instantly made it the best in the league.

But Betts was only one year away from free agency, Corey Seager only two years away, and with a small army about to hit arbitration — Bellinger, Max Muncy, Buehler, and Julio Urías, among others — nobody would have blinked twice if the Dodgers simply said, “Thanks for the 2020 season, Mookie, and best of luck in free agency, but we just can’t simply afford to pay you.” Instead, the Dodgers locked up Betts with a 12-year extension worth $365 million, making it the fifth-largest sports contract of all time. In doing so, they ensured that one of the game’s most electric players and a perennial MVP candidate would spend the rest of his career as a member of the Dodgers.

Why am I talking at length about the Dodgers? After all, this is a Yankees blog, and the first mention of the Yankees, earlier in this sentence, was the 316th word of this piece. Well, the Dodgers are, in many ways, the most similar organization in baseball to the Yankees: a historic team with a massive following in the largest market on their respective coast. They also are, in my opinion, the most well-run big-market organization in baseball. Despite consistently having one of the league’s best farm systems and being one of the league’s best at employing analytics, they do not pinch pennies: in addition to extending Betts, they offered Gerrit Cole a record-setting contract in free agency, then signed Trevor Bauer to a contract worth as much as $40-45 million in any given season.

They’ve also been active at the trade deadline, acquiring Manny Machado in 2018 from the Orioles and, just this past week, Max Scherzer and Trea Turner from the Washington Nationals. The Dodgers are aggressive, and willing to throw their money around; combined with their emphasis on analytics, pitching depth, and positional versatility, they are essentially what the Tampa Bay Rays would be if the Rays decided to, you know, actually pay their players more than the absolute minimum.

Despite the team’s struggles this year, the Yankees are in a similar position as the Dodgers were before the 2020 season. Even before trading for Joey Gallo and Anthony Rizzo, they genuinely were a good team, albeit one that has been beset by underperformance and injuries. With Gallo, Aaron Judge, DJ LeMahieu, Gleyber Torres, Giancarlo Stanton, and Gary Sánchez, the Yankees have a very strong core in place for the 2022 season. They are also, however, at a crossroads: Gallo, Judge, and Sánchez will all be free agents after next season.

Let’s leave aside Sánchez for the moment, because catchers follow different rules when it comes to contracts. Gallo and Judge are going to demand big paydays in free agency, and rightfully so: not only are they two of the best hitters in baseball, they’re also among the league’s better outfielders defensively. I’m not going to speculate on exact contract length and value — Judge is going to be entering his age-31 season when he hits free agency, which muddies the waters somewhat — but rest assured, any team that wants their services will have to back up the money truck into their driveway. In both cases, that team better be the New York Yankees.

Let’s pretend for a second that the luxury tax actually matters. The truth is, the Yankees at the moment have exactly one massive annual salary, Gerrit Cole’s — no, Stanton’s arguagly does not quite count, as the Yankees are only paying $22 million annually, with Marlins paying his salary down. The Dodgers? Betts, Kershaw, and Bauers all have contracts that average about $30 million, and Bellinger and Trea Turner are about to see raises on their $16 million and $13 million salaries via arbitration. The Dodgers are living proof that the Yankees can afford both Gallo and Judge easily.

Even if the team wanted to continue to remain luxury-tax conscious — or if a salary cap is imposed in this winter’s CBA, unlikely as that may be — the Yankees have the money to keep their two big hitters. The team currently has $30 million invested in two relief pitchers, Aroldis Chapman and Zack Britton, a luxury that they could afford when Judge, Sánchez, and the rest of the team’s young players were making close to league minimum. Both their contracts end after the 2022 season, right when those same youngsters hit free agency. Personally, I’m not totally sold that this is a coincidence: simply by letting these two walk, the Yankees free up enough space for one large extension, which means that they only have to find the money for the other.

And they need to. Having the trio of Gallo, Judge, and Stanton in the middle of the Yankees lineup for the next several years would give the Yankees arguably the best 2-3-4 for the next several seasons; by building on this foundation through trades, the draft, and free agency, they should be able to keep their window of contention open for longer. Otherwise, if they fail to lock up a core...well, just ask Cubs fans what happens next.


Why don’t you wait until Gallo strings a couple of hits together before you throw a multi year deal at him.

You think he suddenly forgot how to hit?

Considering how many players in the past have gone from a smaller market team to NYC and completely lost it while still in their prime, I’d rather hedge my bets than risk getting stuck with another albatross contract they can’t get rid of.

Is that you LSJF?


Judge sure. Gallo? He just came here and he needs to prove himself in New York. Plus a decision of who stays is in order. Gallo or Stanton. Plus you have to make room for Florial and the young studs coming up. Pereira, Dominguez and Wells are sure bets to stick. Younger, healthier and cheap.

He just came here and he needs to prove himself in New York


Plus a decision of who stays is in order. Gallo or Stanton.


Pereira, Dominguez and Wells are sure bets to stick

Jesus Montero was a sure bet until he wasn’t. Kevin Maitan had Dominguez-level hype, and then he didn’t. Until the possible becomes actual, have actual good hitters under contract

Jesus Montero was like literally the number 2 or 3 prospect in all of baseball when he came up wasn’t he? I can’t think of a much surer bet than that and still doing nothing lmao. Also some of the people he chose for "sure bets" are really weird. Wells and Pereira look like nice prospects but neither are especially highly touted at this point.

Montero was #3 behind Harper and Trout and was considered the best hitting prospect in the entire MiLB system

I went back and looked at the 2011 top prospects boards and there’s a familiar name in the top 20 of most rankings from that year. Jameson Taillon

Looks like Baseball Prospectus also had Gary and Dellin on the list

Haha yeah. While I want no part of a long-term Gallo deal, no prospect is a sure bet. NONE.

How in the world do you think the Yankees have a choice to simply move Stanton if they wanted to? Big G has a full NTC.


I’d almost rather see Judge and Rizzo if I had to chose. That’s not a knock on Gallo just like the idea of a strong defense in the infield. I’d rather all three.


Give me Rizzo any day of the week. I love how they say anyone can play 1st base until you see him short hop a throw or start a double play off a grounder. That’s why Teixeira was so valuable to those teams.

Judge and Rizzo

definitely Judge and Rizzo , to me better combo than Gallo, but all efforts should be made to keep all three if possible

I'm definitely in the re-sign Rizzo fold.

That should be priority one for Cashman come Nov. 1——-only this time WITHOUT the feet-dragging drama that charachterized the DJL re-signing.
Whatever the CBT threshold, if exceeded Hal’s tax will be re-set to the lowest level. Next year has "if-you’re-gonna-spend-big—-this-is-the-year to-do-it" written all over it. Of course, I’m assuming a CBA that retains a structured CBT with only threshold levels increasing.

God forbid a players strike….that will hurt the game of baseball terribly coming off two years of Covid already wrecking havoc.

Yankees and Dodgers dominance.

I was fortunate to watch both the Yankees and Dodgers go toe to toe in many of the World Series battles during the 1940’s and 50’s; they spent a great deal of their money on scouting and were able to get the best players before the drafts and free agency. Branch Rickey, GM of the Dodgers, said, "Luck is the residue of design," and both the Yankees and Dodgers proved that in dominating their leagues.

What are the chances Freddie Freeman doesn’t re-sign with The Braves? I’d take him and Judge over Judge and Rizzo or Judge and Gallo.

Wishful thinking?

I have a hard time imagine Freeman leaving...but never underestimate cheap owners I guess.

I’m a bit surprised an extension hasn’t been worked out and he will reach free agency. I am expecting him to stay a Brave for his career

same here

I definitely thought they’d extend him but once he hits free agency, I’m not so sure he’s still a Brave next year. He seems like he wants to stay. I’ve heard him talk about his relationship with Chipper and it seems like he’d also like to spend his entire career in Atlanta but I’m really curious to see what money Atlanta offers, what kind of a home town discount he’s willing to take and what other team is aggressive enough to try and lure him away (and how much that costs).

this is excellent John

I wish more Yankee fans realized how much the Dodgers do to continually work to improve their team and they do so while developing young players and spending on free agents so that they’re playing for today while not destroying tomorrow. I also wish the Cubs story gets more attention because that’s almost criminal and that the front office is using this pity party excuse of "oh they were all free agents at the same time and we offered them market value extensions (yeah right) and they didn’t take them so what were we supposed to do?" How about don’t destroy a team that won the WS a few years ago and actually build on their core! It’s also not noted enough that the Cubs have done very little the past few years but just throw their hands up. Enjoy the next 100 year rebuild Cubs fans!

I also like that you point out the money the Yanks get from the Marlins to separate Stanton as a high cost Yankee holding the team back. Nice article John.

Agreed on all points!

Sell them both

Need playoff caliber pitching.

So they can be the 2015 Mets?

All pitching no hitting?

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