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 avoid: Juan Soto

"Avoid a contract extension with Juan Soto?! Are you f---ing stupid?!" Just hoooold up there, buddy. This has nothing to do with the Yankees' desire to keep him in the Bronx, or his fit with New York for the next 12 years.

Soto, as of this moment, doesn't want an extension. His agent, Scott Boras, is probably relentlessly advising against it. If neither of those things were true, the Yankees probably would've sealed the deal over a month ago.

Cashman came out and said, straight up, that almost nothing will prevent Soto from reaching free agency after 2024, something everybody already knew (but thick-headed opposing fans decided to laugh at because they read a headline rather than follow the story for two months).

Trying to work out an extension with Soto feels like it would do more harm than good because of how the line's seemingly been drawn. And if the Yankees are at the forefront of the "business" side of MLB's dealings, they should know better. A player of Soto's caliber and age represented by an agent like Boras does not sign an extension. He tests the open market, which is now beneficial more than ever for the top 10% of players in the game. Shohei Ohtani just got $700 million. Yoshinobu Yamamoto got $325 million. Aaron Judge got $360 million. Manny Machado got $350 million. Corey Seager got $325 million. Xander Bogaerts got $289 million. There is no logical reason, from a business standpoint, for Soto to make the biggest decision of his life before the proper time arrives.

Let the situation play out. Make a deep playoff run. Hell, maybe win a World Series? The Yankees need to provide Soto with a one-of-a-kind environment. The money's already there.