The Yankees must extend both Aaron Judge and Joey Gallo

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.