New York Yankees Offseason Outlook

After coming up short in the postseason again, the Yankees are set for a pivotal offseason where they could lose the face of their franchise.

ANAHEIM, CA - AUGUST 31: Anthony Rizzo #48 is met at the plate by Aaron Judge #99 of the New York Yankees after hitting a solo home run in the game against the Los Angeles Angels at Angel Stadium of Anaheim on August 31, 2021 in Anaheim, California. (Photo by Jayne Kamin-Oncea/Getty Images)

The New York Yankees, once again, crashed and burned their way out of the ALCS just a week ago. For many franchises, a trip to the Championship Series and sustained playoff appearances would be seen as a victory. But for an organization that has stuck by the “Championship or nothing” mentality, the 2022 season seemed like a failure.

There’s an unprecedented amount of talent on this roster. But for some reason, this team can never come through. Much of the criticism in recent weeks has been placed on general manager Brian Cashman, who’s acquisitions of big-time bats and high-priced relievers hasn’t delivered the team a championship in over a decade.

Deals like the Donaldson/IKF trade have caught up to him. It is unclear whether Cashman will stay with the organization, as he is currently out of contract. Only time will tell.

A ton is on the docket regarding the New York Yankees and their offseason. Let’s take a dive into what’s on the board for this franchise as we enter the dead of winter.

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Bringing Back Integral Pieces

It’s been well-documented that the face of the franchise, Aaron Judge, is currently out of contract and will hit the free agent market for the first time in his career. A record-breaking season will earn the slugger one of the bigger paydays we’ve seen in the past few years, and that should be the team’s first priority.

Judge is the heart and soul of the Yankees. A true leader on and off the field. Not to mention, he’s a top-five player in the entire sport. This was originally a necessity for the team last winter, but Judge rejected all contract offers preseason and fully bet on himself. Clearly, it worked out in his favor. The Yankees have to exhaust every resource possible to bring back the outfielder.

While Judge is the most important piece to this Yankees offseason puzzle, he’s not the only integral piece of this core that will hit the free agent market. Four other key Yankees players need to be paid too, and here are the guys the team should look to bring back.

First baseman Anthony Rizzo currently has a player option for the 2023 season that he will reportedly opt out of. Everyone expected the move from the veteran, as he was spectacular this season. He mashed 32 home runs for the fourth time in his career, the second-most on the team.

Rizzo is a key part to the Yankees clubhouse as well as being instrumental to the team on both sides of the ball. Not to mention, he’s created a strong relationship with Aaron Judge. Rizzo deserves a bump up for another three years and could play a part in bringing Judge back to the pinstripes.

Starting pitcher Luis Severino has a $15 million team option for next season that deserves to be exercised. One of the best in the game when healthy, Severino enjoyed a nice bounce-back year after missing time through Tommy John surgery. His 3.18 starter ERA was the second-lowest among anyone in the staff, even better than ace Gerrit Cole. Sevy slots in as a great three-to-four starter for the team. This is a no-brainer move for the Yankees.

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Outfielder Andrew Benintendi was brought to the Bronx at the trade deadline this season for a slew of prospects. The former Red Sox player brought a different kind of dynamic to this lineup, with a more contact-oriented approach and a left-handed bat.

The Yankees as a team have been crying out for a player of Benintendi’s caliber. He suffered a hand injury that caused him to miss the entirety of the playoffs. There’s no doubt in my mind that he would’ve been a difference-maker during that run, as the offense couldn’t even put a ball in play. There seems to be a hole now in left field, and the team should bring him back to fill said void.

The final member of the 2022 Yankees who should be brought back is utility man Matt Carpenter. Carpenter had the best unqualified season ever, finishing with a 217 wRC+ in 154 plate appearances. He provided a veteran presence in the clubhouse that was key down the stretch. And in a pinch, he can play a number of positions.

Carpenter struggled in the playoffs after coming back from injury, but one could only chalk that up to the man not playing baseball in two months. He provides the perfect bench bat and leadership qualities you will find in this class of free agents. Besides, he won’t cost a fortune. And his mustache is gorgeous.

Relieving Some Space

There are a few big contracts coming off the Yankees books this offseason, as well as one they should look to offload. Freeing up this money will allow the team to bring back the names we mentioned before, as well as giving themselves some wiggle room with this winter’s free agent class.

Both relievers Aroldis Chapman and Zach Britton combined for $33 million on the Yankees payroll last season. Britton hasn’t been the same after enduring multiple injuries, and Chapman’s velocity and control were a severe problem. It seems like both have most likely played their last game as a Yankee.

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The Josh Donaldson trade from last season has turned into a complete disaster. On the base of it, the veteran was a plus defender with a below average bat. Once you factor in the fact that he’s owed $21 million next season, that makes it even worse. The Yankees being relieved of that contract would be monumental for their offseason plans.

They’re unable to outright cut the player because of his contract, but there’s still a few options the team can explore. They could package Donaldson with a prospect so it’s more desirable for a team to want to take him on. Or they could just pay the remaining $27 million left on his deal. It’s an interesting topic that this team will have to handle, but I personally think the veteran third baseman will be on this team next season.

Another player they have to explore trade options for is outfielder Aaron Hicks. Hicks signed a seven-year deal with the team back in the 2018 offseason, and it’s been a brutal watch. The center fielder has seen extreme regression, and eventually lost his starting position between Harrison Bader, Benintendi, and Oswaldo Cabrera.

It should be easier to find a trade partner for Hicks as compared to Donaldson. The outfielder is owed around $10 million for the next four seasons and is just 32 years old. Regardless, it’s pointless to pay a fifth outfielder that type of money.

Bullpen Help

The bullpen of the 2022 New York Yankees was a blatant weakness down the stretch. Sure, there are some talented arms in there like Clay Holmes, Jonathan Loaisiga, Ron Marinaccio, Wandy Peralta, Scott Effross, and Lou Trivino, but it simply didn’t stack up with the rest of the teams in the playoffs. With longtime closer Aroldis Chapman out the door, it may be time for the organization to spend big on a reliever once again.

New York reverted to a “closer by committee” style towards the back half of the season. A championship caliber team should not have to resort to this type of decision making. The relievers mentioned before performed their roles effectively. But if there’s one area that this team should spend big on, it should be for a top tier closer.

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Injuries also severely dampened this group towards the end of the season. Holmes and Marinaccio saw IL stints towards the end of the year, and Effross has to receive Tommy John surgery. There needs to be consistency here.

There are slim pickings as far as the top tier closers go, with Kenley Jansen and Edwin Diaz being the two biggest names on the market. Don’t be surprised if this is one of the assets they attack in the following weeks.

Let the Kids Play

There could be a shift in mentality with this New York Yankees team. For decades the team has been known to sell out on their prospects in favor of big-money players. With the commitments of both Gerrit Cole and Giancarlo Stanton, the team might look to the kids to provide production.

In 2022, the Yankees brought up a sizeable number of prospects to get decent playing time down the stretch. Those being Oswaldo Cabrera, Oswald Peraza, Clarke Schmidt and Greg Weissert. All four made key contributions in the final two months of the season. Even making several appearances in the playoffs. Instead of signing the big-name free agents, why not give these four a shot in the lineup every day?

Oswaldo Cabrera became an instant fan favorite once he was called up. He made numerous spectacular plays and became a super-utility man for the team. Known as an infielder, he spent a majority of his time in the outfield this season and became an OAA goldmine in right field. Following Benintendi’s injury, he slotted perfectly into left field.

Peraza is as slick as it comes with the glove. After watching a full year of Isaiah Kiner-Falefa at shortstop, it was refreshing to see the top prospect take over for a few. The bat is still in development, but he can become a solid big-leaguer for the Yankees. Not to mention, if Peraza doesn’t work out, the team still has top prospect Anthony Volpe waiting in the wings.

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Both Schmidt and Weissert were solid relievers for the team during their stints this season. Schmidt started multiple games and was given as shot in the rotation and could still have a role there in the coming years. Weissert was brought up later in the season and saw some growing pains. However, his wipeout slider was deadly, with hitters hitting just .130 against the pitch.

Sure, every fan wants to see their team throw the big bucks at the top tier free agents and call it a day. Especially Yankees fans. But these young guns deserve a shot. Combine the talent you already have on the big-league roster with the top prospects, and it could be a recipe for success.