Yankees’ Most Pressing Questions for Brian Cashman in General Manager Meetings

For inconsolable Yankees fans, take a look at the depth of this time on last year’s calendar.

Brian Cashman was on trial at CEO meetings in Scottsdale, Ariz., where he vigorously defended the club’s performance after an 82-win season and said the Yankees’ processes and people were “pretty damn good.”

With 2024 three wins shy of a World Series title, the temperature will be lower at this year’s meetings in San Antonio, but questions remain about a championship drought that has reached 15 years for the team entering another crucial offseason.

For the first time since the club’s hopes were dashed in a wild Game 5 against the Dodgers on Wednesday, Cashman will speak publicly about a season that showed improvement but not enough for a franchise that has made World Series championships, not appearances, its standard.

Baseball executives are expected to arrive in Texas on Monday before the official start of meetings on Tuesday.

By the time meetings wrap up Thursday morning, there should be more clarity on how the Yankees plan to handle this offseason, and Cashman is set to answer questions such as:

Do the Yankees need a relatively quick response from Juan Soto?

Super agent Scott Boras is eager to take his time, allowing each team to win over their client and watch the bidding war unfold over the next few months.

The Yankees — and any other club willing to compete for Soto — aren’t sure whether they’re committing hundreds of millions of dollars to one of the most attractive free agents the sport has ever seen, or whether that money should be spent elsewhere. .

Cashman feels like such a huge domino must somehow fall in a relatively short time?

If Soto slips, the Yankees will have to turn around quickly.

What happened to Gerrit Cole?

The ace opted out of the remaining four years and $144 million of his contract on Saturday.

The Yankees can keep Cole off the market by playing an extra season worth $36 million, which would keep him at the top of their rotation through 2029.

There was confusion about the deadline for this decision: it was supposed to be Sunday, but then it was determined that it would be Monday. It is unclear whether both sides have agreed to bring him back.

Perhaps the parties are negotiating.

There’s a strong argument to be made that the Yankees can’t afford to risk losing face to their rotation and becoming one of the best pitchers in baseball, even if he’s 34 and starting to show signs of that age.

There’s also a strong argument to be made that the Yankees can’t afford to guarantee a pitcher $180 million if their No. 1 priority is Soto and there are other top starters available.

Can wages increase?

The Yankees’ payroll topped $300 million for the first time in 2024, surpassing the highest luxury tax threshold, the “Steve Cohen tax,” of $297 million.

FanGraphs currently pegs the projection at $245 million for tax purposes next year (which assumes Cole’s return) – and that’s before Soto’s mega-contract and any significant offseason changes.

If the Yankees sign Soto and keep Cole, will there be room for other players?

Or is Hal Steinbrenner stubbornly seeking to cut wages to a level he didn’t want to reach?

In May, he called the 2024 payroll “unsustainable.”

“I broke the record (on this topic): I don’t believe I need to have a $300 million salary to win a championship,” Steinbrenner said at the time. “I think I need a good roster of veterans who will make a lot more money, but we’ve also put a lot of money into our player development system over the last five to 10 years. And in my opinion, we have one of the best players in baseball right now.”

Are changes needed in personnel or coaching to create a more fundamentally healthy team?

The Yankees were able to swallow mistakes in their fielding and base running during the regular season, which ended with the AL East title, and during the two postseason rounds, which ended with the pennant.

But the team that, according to FanGraphs, was rated as the worst ballclub in baseball and constantly hurt itself defensively, paid for its mistakes in the World Series, culminating in a three-error fifth inning in Game 5 that will be remembered.

Are these shortcomings a personnel problem that can be solved through player acquisitions?

Or are these weaknesses a structural problem in which coaching is not strong enough? By the way:

Will Aaron Boone return?

The presumed answer is yes, but there has been nothing official regarding the coach, who has just completed the final guaranteed year of his contract with a club option for 2025.

“We’re certainly excited to have him as our manager,” Cashman said during the ALDS. “We have the best record in the American League (and) we won the AL East. Now we will try to win the postseason and rise to the top.”

For the first time under Boone, the Yankees reached the World Series.

But for the seventh time in a row under Boone’s leadership, they failed to complete the mission. Will it matter?