Yankees in Need of Left Fielder and Bullpen Help

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Before the star outfielder Aaron Judge agreed to a nine-year, $360 million contract with the Yankees, he wanted to make sure the team’s owner, Hal Steinbrenner, knew there was more work to be done. Not just this off-season, but for the duration of Judge’s tenure in the Bronx.

“That was one of the big questions that I asked him,” Judge said during a news conference on Wednesday at Yankee Stadium in which he was named the team’s captain. “If I’m coming back here for nine-plus years, I want to be in contention every single year. I don’t want to just get into the playoffs. I want to be the driving force that is the team to beat in the postseason.”

Judge, who won the American League’s Most Valuable Player Award in 2022, believes Steinbrenner has “backed up his commitment” so far this off-season. He cited the six-year, $162 million contract the team gave to the left-handed pitcher Carlos Rodón, whom Judge called a “bulldog.”

Judge also noted New York’s $40 million guarantee to first baseman Anthony Rizzo and the two-year, $11.5 million deal with Tommy Kahnle, a right-handed reliever who had pitched for the Yankees from 2017-20.

“He wants to win, just like his dad,” Judge said of Steinbrenner and his father, George, the longtime owner of the team who died in 2010. “What the Steinbrenner family has built here and done here with the Yankees is something special. I think he wants to continue to build on that legacy.”

Spending does not guarantee championships, but Steinbrenner has faced criticism from some Yankees fans for not maximizing his team’s financial might amid a World Series drought that stretches back to 2009 — a long wait by Yankees standards. But Steinbrenner has doled out approximately $573.5 million this off-season while retaining Judge, a homegrown superstar, and putting his starting rotation over the top with the addition of Rodón.

That lump sum looks less impressive when compared to the more than $700 million Steven A. Cohen and the crosstown rival Mets have laid out in recent weeks, but Steinbrenner knows there’s still work to be done.

“I’m not going to talk about specifics, but I do have a kind of place I want to land,” Steinbrenner said Wednesday when asked about his payroll goals. “Whether we’re there or not, I’m not going to get into that. But all I can tell you is we’re not done yet.”

One obvious position the Yankees can upgrade is left field, though General Manager Brian Cashman said the team will evaluate any possible improvements moving forward. The rotation, however, looks set with Rodón, Gerrit Cole, Nestor Cortes, Luis Severino and Frankie Montas.

The club has missed out on a handful of free agents in left field, including Andrew Benintendi, whom New York acquired in a deadline trade with the Kansas City Royals last summer. He played 33 games for the Yankees before breaking a wrist in early September. Benintendi recently agreed to a five-year, $75 million contract with the Chicago White Sox — a length the Yankees did not want to go to with Benintendi, a contact-oriented lefty swinger.

Most of the top free agents are already off the board, and even a high-risk option is Michael Conforto, the former mainstay of the Mets, has reportedly agreed to sign elsewhere as well. Outfielders that have been featured in trade rumors include Bryan Reynolds, 27, a star center fielder for the Pittsburgh Pirates, and a group of three young Diamondbacks players: Daulton Varsho, 26 — who can also play catcher — Alek Thomas, 22, and Jake McCarthy, 25.

All of those players hit from the left side or are switch-hitters. The same goes for three internal candidates Cashman mentioned: Aaron Hicks, Oswaldo Cabrera, and Estevan Florial. However, Hicks is coming off a poor campaign and is injury prone, while Cabrera, who made his major league debut in 2022, has limited outfield experience and may be best served in a utility role. Florial, 25, has never had big league success, though his chances have been limited.

“It’s an area that we’d like to improve if we can, but if we can’t, we’re going to go with what we have,” Cashman said Wednesday. In the past, he has made similar comments, only to make a splash later.

“We’re down a left-handed bat, which would fit in left field,” Cashman continued, noting the loss of Benintendi. “So that would be something we prefer. But at the same time, you can’t have everything you want at all times. So we continue to patiently assess opportunities and when something realistic comes into play that we’re comfortable with trying to pull down, we’ll make some recommendations towards Hal. But it’s Dec. 21 and it’s been more of a challenge to solve that. So, we’ll continue to work.”

Left field is clearly at the top of the to-do list, but it wouldn’t be a surprise if the Yankees added another reliever this off-season. The team could also consider trading Hicks or third baseman Josh Donaldson, though it might be hard to find takers for expensive veterans coming off unproductive 2022 seasons.

Whatever happens between now and spring training, Judge, the Yankees’ newly anointed clubhouse leader, is confident that the team will look into, if not bolster, any areas of concern. With his new deal in place, Judge expects the organization to be all in.

“There might be a couple more moves down the road,” he said with Steinbrenner sitting next to him. “I’m not too sure. But I know they’re always working on something to try to improve this team day in and day out, so I think we’re definitely in good hands on that front.”

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