The Yankees’ Offseason To-Do List

Aaron Judge./Getty Images

By Owen Russell 


   Another trip to the playoffs, another season wasted at the hands of the of the nefarious Houston Astros for the New York Yankees. New York has not seen a World Series since 2009, and seeing how the Astros are poised, they may not see one in the conceivable future. What will it take for the Bronx Bombers to reclaim their storied glory and sit on baseball’s mountain top once more?

   After a 99-win season which included a division title, and an ALDS victory over the Cleveland Guardians, some may assume that the Yankees have little work to do in the offseason. That New York can trust the process, and try the same formula next year. Those people are wrong. The American League is only getting stronger. The Houston Astros may own the league currently, but teams like Seattle, Cleveland, Toronto, and Baltimore are all young, hungry, and improving. For the Yankees to compete with the Houston Juggernaut and the rest of the league’s youth movement, they will have to take care of business this offseason. Here are three key issues the Yankees must address this winter:

  • Re-sign Aaron Judge.

   Let’s start with the no-brainer. The Yankees need to lock Judge down for a long time; preferably for life. Judge is coming off an MVP season where he surpassed Roger Maris as the American League home run champ, blasting 62 home runs during the regular season. 

   Maris’ 61 home runs in 1961 culminated in a World Series victory over the Cincinnati Reds. What did Judge earn for his Herculean efforts? A dismal four game sweep in the ALCS, decimating the hopes and dreams of Yankees for a 13th straight season. It was not pretty.

   And yes, Aaron Judge deserves some of the blame. The unquestioned MVP hit .139 with an on-base plus slugging of .490, not to mention he drew just two walks in 38 plate appearances. Judge’s lackluster playoff performance is disconcerting. But don’t forget that this is the same Aaron Judge who led all of the Major Leagues in home runs (62); runs (133); runs batted ins (131); on base percentage (.425); slugging (.686); OPS (1.111); and total bases (391). 

   Judge wasn’t just good this season, his numbers were astronomical. He did it all while batting .311, and drawing 111 walks. There has not been a better statistical season in the past decade.

   The Yankees failed to sign Judge this past season, offering him a seven-year contract for $213.5 million he just was not satisfied with. The deal would’ve made Judge one of the highest paid athletes in the sport, but he thought he deserved more. He was right.

   New York will now have to break the bank on Judge if they expect to make him a Yankee for the rest of his career. Before the season, Judge stated he wanted around $36 million per year for the next 9-10 years, according to the New York Post. After a season like this, it is hard to determine just how much Judge will garner, but there is certainly demand for the 30-year-old superstar. The Mets have already been rumored to be in the mix, and other teams with big banks like the Dodgers or the Giants could make Judge a tempting offer.

   If the Yankees hope to contend for a title in the near future, they must lock down Aaron Judge by whatever means necessary.

  • Figure out the bullpen.

   Hate to harp on Houston again, but take a look at how the Astros have dominated the playoffs thus far. The ‘Stros have put forth dominant pitching. Justin Verlander and Framber Valdez deserve some credit for leading an elite starting rotation, but without their bullpen, Houston may not be where they are right now. In 33 innings pitched this postseason, the Astros’ bullpen boasts a 0.82 Earned Run Average, a 0.73 WHIP (walks and hits per innings pitched), and 42 strikeouts. Compare that to a Yankees bullpen who shoved out a 2.73 ERA throughout their nine playoff games, and the difference becomes obvious. 

   Now the Yankees’ bullpen was not awful. There is room for improvement, though. Aroldis Chapman used to be the anchor which supported this unit through even the rockiest waters, but times have changed. Chapman devolved into a shell of his former self over the last half of the season, culminating with him destroying his career by missing a mandatory practice and being left off the postseason roster. Without Chapman, the Yankees failed to close out games in the final innings. The Guardians stole two wins during the ALDS, courtesy of faulty bullpen pitching.

   How will the Yankees make up for Chapman’s disappearance? Well there is the tried and true Yankee method of spending the most money possible. If New York wanted to find themselves that high-money closer, they need only hop over the East River. 

   Edwin Diaz became a folk hero this past season. His rousing walk from the bullpen, underscored by righteous trumpets, only added to his mythology. Diaz wasn’t just all flare – he had the stuff to back it up. The Mets closer threw 62 innings, in which he tallied 32 saves along with a strikeout percentage of 50.2. That is a strikeout per nine innings rate of 17.2; the closest Yankee reliever, Michael King, earned a strikeouts per nine rate of 11.6.

   Diaz displays the kind of All-Star closer the Yankees need to finish big games. His ability to fan batters in high leverage situations fills a crucial hole in New York’s bullpen. However, he may prove to be too costly. On the open market, Diaz looks to command anywhere from $78 to $100 million for five years, according to the Athletic.

   Is that too much? Diaz has had an up-and-down Mets tenure, but he is fresh off possibly the strongest season for a closer in recent history. If he can repeat 2022’s numbers, then the sky’s the limit.

   If Mets owner Steve Cohen scoops up Diaz, then the Yankees can look elsewhere. Kenley Jansen and Craig Kimbrel, two of baseball’s all time saves leaders, become free agents this fall. Both are past their prime, but could be worth a low risk contract. Besides Diaz and those two, the free agent market does not boast top talent. Regardless of how, the Yankees must make moves to sure up their bullpen this season.

  • Decide whether or not to “sell the farm.”


   The Yankees have a surprisingly strong farm system. For a team with the reputation of catapulting their top prospects the moment they attain trade value, New York has built an exciting group of prospects. It is time to decide if these young players are the plan for the future, or if they can be sold for a Major League ready talent.

   Currently, the Yankees own four Top-100 prospects, according to MLB’s official website. Anthony Volpe (shortstop, 5), Jasson Dominguez (outfielder, 39), Oswald Peraza (shortstop, 50) and Austin Wells (catcher, 82). These four represent a dilemma facing New York’s future. For instance, Volpe and Peraza both play shortstop, both are young and yet both of them cannot be a part of New York’s future. 

   Now take a look at Dominguez. Coming out of the Dominican Republic, Dominguez astounded scouts and earned himself a $5.1 million contract as well as comparisons to MLB legends Mike Trout, Bo Jackson, and Mickey Mantle. All before his 18th birthday. “The Martian,” as he is often referred to, has risen fast through the Yankees organization, reaching AA by the time he turned 19. While he continues to rise, those same scouts who levied lofty expectations on the teenage prodigy have begun to cool off. Would it be in New York’s best interest to trade Dominguez while his value is still reasonably high? Short answer: yes.

   If the Yankees hope to win a World Series in the next few seasons, they must trade some of these high value prospects. The heart of New York’s lineup are all in their early 30s, including Judge, Stanton, and Rizzo (who is a free agent this offseason, but should certainly be re-signed). Strike while the iron is hot. New York does not have the luxury of patience or time to see if four kids in their late teens or early twenties can hack it in the Majors. Ideally, the Yankees would be able to create a package around at least one of these prospects, and receive a top Major League talent. 

   Just this past summer, the Yankees shipped three prospects to Oakland and received pitchers Frankie Montas and Lou Trivino. Though Montas struggled with injuries, Trivino helped bolster the Yankees bullpen over the back-half of the season. Montas will likely turn things around next year, and become a key contributor for the Yankees rotation, while three prospects New York sent to Oakland all rank lower than the four listed above. 

   If New York wanted to create a blockbuster trade, they could use San Diego’s strategy which plucked Juan Soto and Josh Bell from the Washington Nationals. The Padres sent four of their top prospects for the 23-year-old phenom Soto, and the All-Star first baseman Bell. There does not look to be a talent like Soto on the market. There rarely is, but New York surely has options. 

   The Boston Red Sox look to be sliding face-first into a rebuild, and in doing so, they may need to sell off some of their star talents. Third baseman Rafael Devers would be an ideal fit for the Yankees. His mix of power and dependability at the plate could help ignite the New York lineup. If not Devers, then there may be an even bigger prize for the taking. 

   There could be a world where the Yankees trade for living legend Shohei Ohtani. The Angels’ pitcher/designated hitter Ohtani has stated that he does not want to stay in Anaheim for long, according to Jon Heyman of the New York Post. It would require an incomprehensible bounty, but bringing Ohtani to New York exists somewhere out in the infinite multiverse.

   Regardless of how New York wants to slice it, they need to move on from some of their prospects this offseason. Preferably the team should keep Volpe, but the rest of them can go. Hopefully the team can get a deal done, otherwise they are at risk of wasting their window.


   The Yankees have been floundering in success for far too long. Their constant winning seasons and frequent playoff appearances can no longer distract fans. New Yorkers expect championships. The team has a strong base. They showcase a formidable lineup, bashing the most home runs in the MLB this season. Their starting rotation features Gerrit Cole, one of baseball’s preeminent strikeout artists. They just lack a few pieces which could put them over the edge.

   Whatever it may be, the Yankees must take action this offseason. If they fail to act, they may fall behind the American League’s up-and-coming competitors. Not to mention the mighty Houston Astros.

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