It has been nearly 15 years since the New York Yankees last won the World Series. In 2023, they flirted with a losing record for the first time in more than 30 years. It is time for the Yankees to bring back the evil empire, remember what made them the Yankees, and ultimately get back to their winning ways. This means making a Juan Soto trade and signing Yoshinobu Yamamoto this offseason. 

As the architect of the Yankees roster, Brian Cashman has been feeling the heat from the fan base, and there are rumors that he has been feeling the heat from ownership as well. Hal Steinbrenner is also feeling pressure from the fan base to deliver a winning product.

The Yankees of old would have identified their primary needs, found the best players to fill those needs, and done whatever it took to acquire them. Think of the 2008-2009 offseason, when the Yankees went out and acquired CC Sabathia, AJ Burnett and Mark Teixeria. The next season, they won the World Series.

This offseason, New York needs to go out and get another top-tier starting pitcher, as well as some more “savages in the box” for Aaron Boone’s squad.

Key priorities


This offseason, the key priorities for the Yankees are a left-handed, middle-of-the-order batter who can hit for power and get on base at a high average, an outfielder, and a starting pitcher who can be a #2 starter with ace potential.

Juan Soto clearly checks off two of these categories and Yoshinobu Yamamoto checks off the third. The Padres are likely looking to trade Soto to free up payroll as he has one year left before free agency and will likely command $30 million in arbitration, and Yamamoto, 25, was recently posted to MLB following an incredibly successful career in Japan.

In order for the Yankees to have a successful offseason, they must find a way to acquire both of these players. They have to return to their roots as the Evil Empire. This week’s Winter Meetings will be the first opportunity for Brian Cashman to acquire the players his team needs to compete for a World Series title.

High-profile international free agent

Signing Yamamoto will likely be the first domino to fall, for a variety of reasons. First, it is easier to negotiate financial terms and come to a contract that just costs money than it is to negotiate a trade where you are surrendering assets.

Second, the Padres are in desperate need of pitching. This means that the Yankees will likely have to give up several of their best pitching prospects or young big leaguers for Soto. Players that could find themselves on a flight to San Diego in such a deal include Michael King, Clarke Schmidt, Drew Thorpe, Everson Pereira, Jhony Brito, Randy Vazquez, and even possibly Nestor Cortes.

The Japanese star fills a key need for the Yankees — a second ace-level pitcher to pair with Gerrit Cole. The two of them would form a formidable duo, especially in the postseason, where starting pitching can dominate a game and shut down an opposing lineup. Nestor Cortes, if he isn’t included in a potential Soto trade (which he likely won’t be), profiles perfectly as a number-three pitcher. This role would allow Cortes to maximize his ace-level ceiling while reducing the negative impact of his injury history and inconsistency.

If the Yankees are able to sign Yamamoto, it will make it much easier for Cashman to trade away a few of his pitchers or top pitching prospects knowing that Yamamoto is on the roster to be the Robin to Gerrit Cole’s Batman.  

Left-handed slugger and on-base machine

Juan Soto between the Padres and Yankees logos

The next step towards the perfect offseason for the Yankees is to successfully pull off a Juan Soto trade with the Padres. 

The Yankees need at least one, but preferably two, reliable bats that can get on base consistently and ideally hit for power as well. Soto passes all of these tests with flying colors, as he is a left-handed on-base machine with a career on-base percentage over .400 in addition to being an underrated slugger who hit 35 home runs last season and has 160 to date in his career. 

In addition to hitting for both average and power, Soto’s ability to generate walks is elite and his eye has been compared to Barry Bonds and Ted Williams.

For a Yankees team that also needs to get younger and healthier, Soto is a perfect fit. At 25 years old, he may not be the most athletic player on the field but he has a clean bill of health. He has proven his ability to stay on the field and to produce. In six professional seasons, Soto has a career OBP of .421 to go with a .945 OPS. 

Soto checks every box for New York, and he is a perfect fit. His left-handed swing also seems as if it was specifically designed to play in The Bronx, where he can take advantage of the short porch in right field at Yankee Stadium.

Other free-agent signings

Brian Cashman and the Yankees should also consider other acquisitions as well. Three players who could solidify their depth and further bolster the team’s championship aspirations are OF/1B Cody Bellinger, OF Jung Hoo Lee, and P Jordan Montgomery.

Bellinger is much more than depth. In an ideal world, he would slot in as the third-best offensive player on the team, behind Judge and Soto. A former Rookie of the Year and MVP, Bellinger has all the talent in the world, although he has been injured and inconsistent in recent years before a resurgent 2023. The best free agent hitter this winter not named Shohei Ohtani, the 2023 version of Bellinger would be a welcome addition to the Yankees roster.

Bellinger’s injuries should concern the Yankees, but given that his major injuries appeared to be bad luck more than anything that could be recurring (a shoulder injury, fractured leg, and broken ribs, as opposed to hamstrings and soft tissue injuries that an be nagging for years), it shouldn’t be a major concern. It is also likely that the injuries significantly contributed to his underperformance in those seasons. 

Although these concerns shouldn’t stop New York from signing Bellinger, a Bellinger contract should be a secondary offensive priority after trading for Soto. His contract should also reflect these concerns. A longer-term contract at a lower annual average value (12 years, $19 million AAV for a total of $228 million) or a shorter contract with higher annual pay (7 years, $28 million AAV for a total of $196 million with an early player opt-out) would be ideal offers. Adding both Soto and Bellinger to play alongside Aaron Judge can help the Yankees get back to their Bronx Bomber roots and fulfill Brian Cashman’s vision of the team being a fully operational Death Star.

Among other potential signings during this winter’s free agency period, Jung Hoo Lee is an elite defender in center field with top-tier athleticism and excellent contact and on-base ability in the KBO. Jordan Montgomery is a former Yankee and the southpaw has grown immensely since his last stint with New York. Bringing back Montgomery and signing Yamamoto would allow the Yankees to trade significant prospect capital to San Diego to help acquire Soto while also fielding a formidable starting rotation. The top four pitchers would be Colo, Yamamoto, Cortes, and Montgomery. 

The Bottom Line

The bottom line is that the Yankees have two significant holes on their roster, and it is essential that Cashman finds a way to land players that address these needs. Luckily for Cashman and the Yankees, the top two players widely expected to be available this offseason, whether through trade or free agency, fit both of these needs.

The Yankees must do everything in their power to acquire both Yoshinobu Yamamoto and Juan Soto this offseason. If the Yankees can bring in “YamaSoto,” they should be in an excellent position to make the playoffs and contend for their 28th World Series title. Additional signings could strengthen the team’s chances to win the Fall Classic and bring another championship banner home to The Bronx.