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Yankees 2023 Offseason: A Franchise-Defining Winter Lies Ahead

The New York Yankees have come to a fork in the road. They should take it.

The 2022 New York Yankees were a good team. They hit more home runs than anyone else in Major League Baseball, ranked third in team ERA, and won 99 regular season games while playing in an American League East that sent three teams to the postseason.

But like every Yankees team that’s come before them in the past decade, they were not good enough.

That was abundantly clear in the American League Championship Series. Sure, they could have fallen into four wins in seven games against the Houston Astros, but they were never the better team. The Yankees had good starting pitching; the Astros have better. The Yankees’ bullpen did well considering the injuries it had to deal with; the Astros’ pen is a death machine. Their lineup featured plenty of pop; the Astros’ have no holes, 1-9.

The franchise that prides itself on winning championships has not done so since 2009 (which, for any other team would hardly be worth noting). In 2017, they came within a game of returning to the World Series, falling to those same Astros in seven. Since then, the gap between the two clubs has only widened. The Astros have developed their talent, made great trades, and brought in the right free agents. The Yankees have seen most of their home-grown talent regress in the majors, stayed quiet at too many trade deadlines, and sat by as other teams signed the major stars.

As it stands, the Yankees should be good next year. There’s just no reason to believe they should be good enough to reach the World Series unless they make some changes.

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New York Yankees Offseason To-Do List

Re-sign Aaron Judge

If the Yankees don’t bring Aaron Judge back, then nothing else matters. It’d be as clear a signal as possible that the team just does not care about winning baseball games nearly as much as it does about saving money. Judge made a huge bet on himself last offseason and it’s paid off in ways no one could have predicted. The Yankees need to do whatever it takes to keep him around, then go from there.

Since there’s no further debate or analysis needed here, I’ll add this: The day the Yankees announce his signing, they should also name him team captain. He’s the best player on the team, the face of the franchise, and the most recognizable player in baseball. He’s earned it on and off the field.

Determine who is running the team

The Yankees signed manager Aaron Boone to a three-year extension last October when fans were already unhappy with him. After another postseason humiliation against a hated rival, Boone is again on the hot seat.

While fans have questioned lineup decisions and bullpen moves, Boone’s saving grace was supposed to be his clubhouse management. But in the playoffs, the team had two notable communication breakdowns: One where Clay Holmes says he told the team he was available to pitch in Game 3 of the ALDS, while Boone thought he was unavailable. Luis Severino even publicly questioned what was going on there. The second came when Boone moved Harrison Bader into the leadoff spot, only for Bader to find out from the media. From an outsider’s perspective, Boone seems to have lost both the fanbase and the clubhouse.

General manager Brian Cashman has been at the helm for four World Series titles and has put the Yankees in the playoffs almost every year since the mid-90s. More recently, he should be commended for pulling the Bader trade at the deadline — something that seemed to make no sense at the time, and then Bader went nuclear this postseason and was one of the only bright spots in an otherwise agonizing couple of weeks.

But his missteps can’t be ignored. Frankie Montas was ineffective before an injury sidelined him late in the year. Isiah Kiner-Falefa frustrated fans all year at shortstop and at the plate. Josh Donaldson was underwhelming in the regular season and then downright awful in the postseason. Jose Trevino was awesome in the first half then cratered to the point that he became a liability. Cashman’s contract is up and you could argue that it’s time to move on.

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Figure out the Infield

The Yankees have a choice here. They can go after upcoming free agents like Trea Turner or Carlos Correa, or they can commit to one of the rookies, Oswald Peraza or Oswaldo Cabrera. But they have to take one of those two options. What they can’t do is find another half-measure like Kiner-Falefa — somebody who makes too many mistakes in the field and is a below-average hitter (84 OPS+). To IKF’s credit, he hit for average and was solid in the postseason, but that doesn’t undo a full season of mishaps.

Then there’s third base. The Yankees committed $44 million to Donaldson last offseason — an absurd amount for someone clearly past his prime — and it predictably backfired. Can the Yankees eat the $21 million remaining on his deal and just release him? Or maybe package a couple of prospects with him in a deal that could maybe land something in return? The third base market isn’t great this offseason, but that’s not necessarily a problem. Cabrera, Peraza, and DJ LeMahieu all give the Yankees some infield flexibility.

Strengthen the pitching staff

The Yankees’ starting pitching was not the problem in the postseason — I’d even argue Gerrit Cole, Nestor Cortes, Luis Severino, and Jameson Taillon performed better than their numbers indicated. But the team can’t just resign Taillon and call it a day. Injuries happen. Guys underperform. The Astros seem to have four aces. Fortunately, there are some intriguing options — Jacob deGrom, Carlos Rodon, Justin Verlander, and Clayton Kershaw to name a few, but it’s unlikely the Yankees will resign Judge AND improve the infield AND sign a top-tier starting pitcher. Don’t panic if the Yankees don’t take one of the above names, as there are other options out there.

Find a catcher

Wilson Contreras is set to become a free agent and is one of the best-hitting catchers in the game. He’d make a ton of sense for the Yankees, who found themselves with too many dead spots in the lineup. Christian Vazquez is also an option if they can stomach someone who spent time with the Red Sox and the Astros last year.

Changing Course

This offseason is going to say a lot about what the Yankees’ priorities are. This isn’t like recent offseasons where they chose not to pursue superstars like Bryce Harper or Manny Machado, who could have put the team over the top. Except for at pitcher, the names aren’t quite as big. But there are options to fill every team need. Good ones.

The Yankees haven’t been cheap the past few years, but they’ve spent money in a way that seems to say “we’re smarter than you,” only to be wrong just about every time. They spent big on Donaldson, thinking he could still be elite in his age-36 season, and he was booed off the field in the ALCS. They gave Aaron Hicks a long-term deal that would have been team-friendly if he didn’t become borderline unplayable. Zack Britton and Aroldis Chapman, somehow, made a combined $32 million this year.

Over the last couple of months, lineup decisions have indicated the Yankees maybe can admit when they’re wrong — albeit only after enough evidence emerges to fill 100 chicken buckets. Whether they do that again this offseason will tell us how OK they really are with being second-best in the AL.

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About The Author
Russell Steinberg
Russell Steinberg
Russell Steinberg is an editor and writer at Boardroom. He came to the brand in 2021 with a decade of experience in sports journalism, primarily covering college basketball at SB Nation as a writer, reporter, and blog manager. In a previous life, he worked as a social media strategist and copywriter, handling accounts ranging from sports retail to luxury hotels and financial technology. Though he has mastered the subtweet, he kindly requests you @ him next time.
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