Think back to the winter of 2023. Yoshinobu Yamamoto’s name was one of the hottest on the free agent market. He spent weeks working out in Los Angeles, where the Dodgers were chasing him and where he also met with the New York Yankees. But he also flew across the country to take another meeting in Manhattan with the Yankees, who wanted him badly. At the time, Gerrit Cole had won the American League Cy Young Award. They also were hoping for a rebound from Carlos Rodón, a repeat breakout performance from Nestor Cortes Jr. and a step forward from Clarke Schmidt and Luis Gil.

In the end, the Dodgers wound up with Yamamoto, giving him $325 million, and the Mets offered a similar deal. The Yankees finished third with a $300 million offer. It’s long been speculated that Yamamoto always wanted to end up with the Dodgers, where he’d stay on the West Coast and play with Shohei Ohtani. But the Yankees were serious in their pursuit of Yamamoto.

Which leads us to this week’s top mailbag question, from reader Richard C.:

Will the Yankees be aggressive in trying to land Tatsuya Imai? Or will they aim lower?

The Yankees are expected to earnestly pursue Imai as they continue to survey the entire pitching market for an arm, according to a league source. The 27-year-old would represent an upgrade to just about any rotation, but particularly to the Yankees’ group, which has so many questions heading into spring training. But don’t be surprised if they end up going cheaper if the price ratchets up for the right-hander.

Right now, it’s too early to say how aggressive the Yankees will be with particular pitchers. They would be doing themselves a disservice by not monitoring everything — and that’s what they do every offseason. For example, general manager Brian Cashman last week said the org spoke on the phone with Casey Close, the agent for righty Michael King, who would make plenty of sense for the Yankees to target and may even be a better option than Imai, who hasn’t played in the majors and may only have mid-rotation upside.

The situation the Yankees currently face is unique. They hope to get Rodón (elbow surgery) back by late April or early May, Cole (Tommy John) back by May or June and Schmidt (Tommy John) around August. Provided the returns go as planned, they would be adding them to a group featuring Max Fried, Luis Gil, Will Warren and Cam Schlittler.

On paper, that’s already too many arms for one rotation. In reality, injuries are unpredictable, and who knows whether they’ll all be healthy.

Adding one more healthy and steady arm to that mix sounds prudent. It would also allow the Yankees to potentially trade from their pitching depth, which is an envy of the industry. Elmer Rodríguez, Ben Hess, Bryce Cunningham and Carlos Lagrange are all considered well-regarded pitching prospects, and there are surely situations in which the Yankees could use any combination of them in a trade to boost their roster elsewhere.

So, yes, Imai — with his mid-90s fastball and four-pitch package — will have the Yankees’ attention, especially after his comments Monday that he would “rather take them down” than sign with the Dodgers.

Imai Tatsuya, a posted MLB-ready pitcher, would like to take down a team like the Dodgers rather than join them. 👀

(H/T TV Ashai, @jomboymedia) pic.twitter.com/I3mtzmnYxI

— TSN (@TSN_Sports) November 24, 2025

If the Yankees re-sign Cody Bellinger, would there be an effort to use him at first base to give Jasson Domínguez a regular shot in left field? — Anthony C.

Don’t count on it.

If the Yankees sign Bellinger and Domínguez ends up the starting left fielder, it’ll be because dominoes fell elsewhere. In that scenario, it would seem likely that the Yankees decided to put Ben Rice behind the plate full time and moved on from Austin Wells. That seems unlikely. Wells is still an above-average defensive catcher who the Yankees hope could still show the promise his bat displayed through the minors and at various points in 2024. The Yankees highly value defense behind the plate, and while Rice has held his own there, he might be better off longterm at first base.

Left field is hard, especially at Yankee Stadium, and the Yankees surely recognized the difference between having Bellinger over Domínguez there last season. Also, with the nine figures that Bellinger is likely to procure, the Yankees probably won’t want to up his first base usage until he runs out of steam in the outfield. Credit to Domínguez for going to the Dominican Republic to work on his defense and right-handed hitting. But he might be looking at a future where he’s a fourth outfielder or traded if the Yankees re-sign Bellinger.

Should the Yankees trade their top prospects now to capitalize on the remaining high-end years of Cole and Aaron Judge? — Peter G.

Peter’s question also referenced how many Yankees hitting prospects haven’t worked out in recent years, a list that included Anthony Volpe and Wells, alongside Miguel Andujar and Greg Bird.

The Yankees shouldn’t be shy about trading their top prospects for proven MLB talent, but there’s something missing from that equation. Rosters need a balance between higher-end players and young, cost-controlled talent. The Yankees can’t just sell the farm, cross their fingers that everything works out and not have a longterm plan. So, no, the Yankees shouldn’t just flip top shortstop prospect George Lombard Jr. tomorrow. They should hope that he’s part of a mix that stays in the Bronx for years to come.

What are the chances the Yankees trade Spencer Jones? — Anonymous U.

Everything short of a starting job in the outfield on Opening Day appears on the table for the 24-year-old. The educated guess here is that the Yankees hold him into spring training to see what he’s got. (If Jones isn’t around, it’s because he’s been used as a piece of a major trade, and it’s too early to predict that.)

Jones had a breakout 2025, crushing 35 home runs between Double A and Triple A. But the 35.4 percent strikeout rate has to be terrifying. For reference, Ryan McMahon led the majors in strikeout rate at 32.3 percent. That’s not going to play in the major leagues. Jones is going to have to show he can decrease his strikeouts before the Yankees give him a regular chance.

Oswaldo Cabrera in the mix to start at shortstop on Opening Day? — Aron C.

José Caballero is slated to be the starter until Anthony Volpe (shoulder surgery) returns. Cabrera’s rehab (broken ankle) is going well, and he was moving around a lot during pregame workouts in the playoffs. But the Yankees like that Cabrera can cover shortstop when needed, and he’s in many ways a key part of the soul of the clubhouse. But Cabrera does seem more likely to end up in his familiar utility role. It was interesting, though, that during the GM Meetings, Cashman didn’t rule out an upgrade at shortstop over Caballero.

“Right now,” Cashman said, “Caballero’s the guy by default, and if we find run into something even better, great. And then we’ll assess what that cost of acquisition is and go from there.”