2 contract extensions the Yankees should pursue, 2 they should avoid in 2024

The 2024 New York Yankees, as Brian Cashman said on the Talkin' Yanks podcast, "need to win." Just look at how the roster is constructed. "The time is now," Cashman added. He's usually not very revealing, so that type of candor emphasizes the urgency fans have felt without it being directly communicated to them.

The Bombers have 10 players slated for free agency after this coming season: Juan Soto, Gleyber Torres, Anthony Rizzo (option), Alex Verdugo, Clay Holmes, Tommy Kahnle, Jonathan Loaisiga, Caleb Ferguson, Lou Trivino and Luke Weaver. They're also going to have to give Gerrit Cole a 10th year on his contract for $36 million to avoid him becoming a free agent.

Some of that was of the Yankees' own making. They acquired all of Soto, Verdugo and Ferguson via trades. They signed Trivino and Weaver to one-year deals. They have not spoken about a contract extension with Torres. They gave Cole the opt-out clause.

As you can see, a balancing act must take place. Cashman can't head into 2025 with this many impact players coming off the books. Then again, it's best to wait it out to see who might be worth securing sooner rather than later.

And don't forget, there are plenty of others the Yankees can approach about extensions to help clarify their future financial picture. What might be the best plan of action for New York?

*Gleyber Torres has been excluded from this list because it's been an exhausted conversation, and it's evident the Yankees want 2024 to play out before negotiating with the slugger.*

2 contract extensions the Yankees should pursue, 2 they should avoid in 2024

Yankees contract extension to avoid: Anthony Rizzo

Anthony Rizzo is definitely a beloved player, but there's undoubtedly some underlying resentment surrounding his signing. The Yankees could've had Matt Olson or Freddie Freeman if they tried harder, but they instead settled on paying Rizzo $20 million a year.

Again, Rizzo is an accomplished player, but he's on the back nine of his career (and closer to hole 18), which makes the Yankees older, slower and less athletic. Freeman probably should've been the aging exception for a free agent signing, but it is what it is.

Rizzo delivered a very good 2022 season, but a freak injury in 2023 derailed everything. "Cognitive impairment" following a collision with Fernando Tatis Jr. affected him for two months before the Yankees decided to do anything about it (more the team's fault than anything else).

But entering his age-34 season in need of a serious rebound (remember, he essentially missed all but two months of last season) probably has the Yankees more inclined to pay his $6 million buyout for 2024 rather than accept his $17 million team option or extend him another year or two. The Yankees need that Juan Soto money handy, and committing more to Rizzo would probably be another repeated mistake.

Yankees contract extension to pursue: Anthony Volpe

Anthony Volpe's rookie season was successful. It wasn't perfect. It was hardly devoid of blemishes. And there's developing to be done. But a Gold Glove/20-20 campaign for his first 162-game slate is the definition of great potential.

More importantly, however? The Yankees know exactly what Volpe needs to work on in order to grow and be the franchise cornerstone he's envisioned as. His defense needs minor tweaks, and that'll come with more reps. His offensive approach is hit or miss, and he'll just need to cut back on striking out and chasing, while being a bit more patient at the plate. Very few rookies burst onto the scene with a sparkling profile that screams "All-Star."

Volpe's stretches of success in 2023 (on a horribly constructed and vibe-cursed Yankees roster, mind you) were notable and highlight-worthy. He's constantly praised by the organization and his teammates for his hard work and attitude, so why not give him security and declare him a franchise piece with a mid-tier, $150 million gamble? Nothing will ever look worse than Aaron Hicks' $70 million extension, so the only place to go is up.

Bobby Witt Jr.'s $288 million extension might've given the Yankees an opportunity to evaluate Volpe's market after one season. Maybe Volpe accepts, maybe he opts to take it year by year. Either way, it's worth a try because this can help set the payroll flexibility for years to come.

Yankees contract extension to pursue: Jasson Dominguez

Like Volpe, Dominguez is very, very green. His eight-game cameo with the Bombers last year had us all floored, but then a UCL injury landed him on the shelf (and he'll be out until the middle of this summer). He's also played just 17 games above Double-A.

But again, this is another name the Yankees have been unwaveringly confident with, refusing to even entertain in trade talks for the biggest stars in the sport. That doesn't mean they're ready and willing to jump the gun right now, but it at least has to be a thought, right?

Scouts have been gushing over Dominguez's five tools ever since he was signed out of the Dominican Republic back in 2019. He's received pretty cool (but unfair) comparisons to Mickey Mantle and Mike Trout. Though Yankees fans have kept their expectations tempered, they couldn't help themselves when Dominguez lit up spring training and then (finally) debuted in September, taking Justin Verlander deep in his first career at-bat in Houston to propel the Yanks to a series sweep.

How about $100 million for Dominguez? Ronald Acuña Jr. got $100 million after a Rookie of the Year campaign in 2019 and the Braves have been reaping the benefits every single day. If Dominguez returns to the Bombers and starts raking in the summer, that should be the number. If the two sides discuss this before he's back from injury, it should look more like Michael Harris II's eight-year, $72 million contract. But we doubt the Martian will settle for that.

Either way, Dominguez's name recognition and player profile fit New York (and anywhere, really) perfectly. Letting both his and Volpe's situations "play out" isn't in the team's best interests. One needs to be prioritized on the extension front.