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

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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.