What Will the Yankees Do This Offseason?

Will the Yankees make a splash this offseason and go after some big-name free agents? Or will they stay the course and continue to build their farm system?

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The Yankees’ Current Situation

The Yankees’ Roster

The Yankees have a very good team. They have a great lineup, a solid rotation, and a good bullpen. However, they have some holes. They could use another starting pitcher, a left-handed reliever, and a right-handed bat off the bench. In addition, they will need to decide what to do with their impending free agents.

The Yankees’ Farm System

The Yankees currently have the best farm system in baseball according to multiple rankings. They are loaded with high-ceiling, young talent that is either close to the majors or still developing in the lower levels. Many of these prospects are outfielders, which is both a blessing and a curse. The Yankees have one of the best outfields in baseball with Aaron Judge, Giancarlo Stanton, and Aaron Hicks. All three are under team control for at least the next four seasons. Brett Gardner is also under contract for 2019 with a team option for 2020. The Yankees also have Clint Frazier, who many believe is the best outfield prospect in baseball, as well as Estevan Florial, who is one of the top-100 prospects in baseball.

The Yankees have a surplus of outfielders and it is one of their biggest strengths as a team. However, it is also one of their biggest problems. The Yankees have too many good outfielders and not enough spots for them all to play regularly. Something has to give and the Yankees will likely look to trade from this surplus this offseason.

The Yankees’ Potential Moves

With the Yankees’ season coming to an end, fans are already looking ahead to next year and what the team might do to improve. The Yankees have a few needs, including a starting pitcher, a left fielder, and a backup catcher. They also have some financial limitations. Here’s a look at some of the Yankees’ potential moves this offseason.

Free Agents

The Yankees have a few big names they will have to make decisions on this offseason. They have until five days after the World Series ends to decide whether or not to extend a qualifying offer to their free agents, which is worth $17.9 million for the 2019 season. If they extend the offer and the player rejects it, the Yankees would receive draft-pick compensation if that player signs with another team. The players who are eligible for free agency and could receive qualifying offers are:

Brett Gardner- OF
Didi Gregorius- SS
CC Sabathia- SP
J.A. Happ- SP
Sonny Gray- SP
Lance Lynn- SP
David Robertson- RP
Zach Britton- RP


The Yankees have been linked to a lot of trade rumors this offseason.

One of the more popular rumors is that the Yankees are interested in acquiring Miami Marlins catcher J.T. Realmuto. Yankees GM Brian Cashman has said that the team is always looking to upgrade at every position, so it makes sense that they would be interested in Realmuto, who is one of the best catchers in baseball. The Marlins are said to be asking for a lot in return for Realmuto, so it remains to be seen if the Yankees will be willing to part with the necessary prospects.

Another big rumor is that the Yankees are interested in free agent pitcher Dallas Keuchel. Keuchel is a former Cy Young winner who would bolster an already strong Yankees rotation. The Yankees are said to be willing to spend big this offseason, so it’s definitely a possibility that they could sign Keuchel.

The Yankees are also said to be interested in free agent outfielder Bryce Harper. Harper would be a huge addition to the Yankees lineup, and they have the money to sign him. However, it remains to be seen if Harper is actually interested in signing with the Yankees.

Finally, the Yankees have been rumored to be interested in trading for Baltimore Orioles’ star third baseman Manny Machado. The Orioles are reportedly looking for a haul of prospects in return for Machado, and it’s unclear if the Yankees would be willing to part with that many prospects.

Rule 5 Draft

The Rule 5 draft protects players who are not on a team’s 40-man roster by keeping them off other teams’ radars. A team must keep a player on the 40-man roster for the entirety of his first four minor league seasons or he becomes eligible for the Rule 5 draft. Once a player becomes Rule 5 eligible, he can be drafted by another team for $50,000. The selecting team must then keep that player on its 25-man roster for the entire season or offer him back to his original team for $25,000.

The Yankees have had success in recent years with players they’ve taken in the Rule 5 draft. In 2017, they took right-hander Luis Cessa from the Detroit Tigers and he’s been a valuable member of their bullpen over the past two seasons. In 2018, they took left-hander Nestor Cortes Jr. from the Baltimore Orioles and he was also a key reliever for them last season.

This year, the Yankees took right-hander Michael King from the Miami Marlins with the first pick of the Rule 5 draft. King is a 23-year-old who pitched to a 2.48 ERA in 22 starts between Single-A and Double-A last season. He’s unlikely to crack the Yankees’ starting rotation next season, but he could be a valuable depth option for them if he can make adjustments at the Triple-A level.

The Yankees’ Offseason Plan

The Yankees have some big decisions to make this offseason. They need to decide what to do with pending free agents like J.A. Happ, Dellin Betances, and Didi Gregorius. They also need to decide if they’re going to pursue any big-name free agents. The Yankees have some tough decisions to make, but they’ll be able to field a competitive team no matter what they do.

The Yankees’ Priorities

The Yankees have a few priorities this offseason. First, they need to address their starting pitching. They also need to add some depth to their lineup, especially at first base and in the outfield. Lastly, they need to figure out what to do with Dellin Betances and decide if they’ll bring him back or not.

Starting pitching is the Yankees’ biggest need. They have a few options in free agency, but they will most likely focus on re-signing Masahiro Tanaka and J.A. Happ. They could also go after Gerritt Cole or Stephen Strasburg, but those two will be very expensive and the Yankees may not want to spend that much money on starting pitching.

The Yankees also need to add some depth to their lineup. At first base, Greg Bird is the only true first baseman on the roster and he has struggled with injuries throughout his career. In the outfield, Brett Gardner is getting up there in age and Aaron Hicks is coming off of an injury-plagued season. The Yankees will likely look to sign a free agent outfielder like Avisail Garcia or Nicholas Castellanos to help bolster their outfield depth.

Lastly, the Yankees need to figure out what to do with Dellin Betances. Betances is a free agent and he is coming off of an injury-plagued season. The Yankees have expressed interest in bringing him back, but they may not want to give him a big contract after he missed most of last season due to injury.

The Yankees’ Budget

The New York Yankees have a lot of decisions to make this offseason, as they try to rebound from a disappointing 2019 campaign. The Bronx Bombers have several free agents to worry about, including starting pitchers Masahiro Tanaka and J.A. Happ, infielders Didi Gregorius and Brett Gardner, and catcher Austin Romine. In addition, the Yankees have several arbitration-eligible players, including right fielder Aaron Judge and starting pitcher Luis Severino.

With all of these potential moves on the horizon, the Yankees’ front office will have to make some tough decisions about how to allocate their resources. According to Spotrac, the Yankees currently have a little over $170 million committed to salaries for 2020, which gives them some flexibility to make some major moves this offseason. However, the Yankees will also have to account for raises for their arbitration-eligible players, which could eat up a significant portion of their budget.

If the Yankees are going to be active in free agency or make any big trades this offseason, they will need to free up some salary space. One way they could do that is by trading away Gardner or Ellsbury, two veterans who are scheduled to make a combined $27 million next season. The Yankees could also look to move one of their young outfielders, such as Clint Frazier or Aaron Hicks, in order to free up playing time for Judge and Giancarlo Stanton.

Another way the Yankees could create some financial flexibility is by shedding some of their expensive veterans via trade. Lance Lynn ($9 million), Dellin Betances ($7.25 million), and Sonny Gray ($7 million) are all scheduled to become free agents after next season and could be attractive trade targets for teams looking for cost-controlled pitching. The Yankees could also look to trade away JA Happ ($17 million), who struggled mightily last season but still has two years remaining on his contract.

The Bottom Line: The New York Yankees have several important decisions to make this offseason as they try to bounce back from a disappointing 2019 campaign. With several key free agents and arbitration-eligible players on the roster, the Yankees will need to carefully allocate their resources in order to create a competitive team for 2020 and beyond.


It’s been a rocky start to the offseason for the New York Yankees. They’ve been linked to free agent Gerrit Cole, but he recently signed with the Los Angeles Angels. They also missed out on Zack Wheeler, who agreed to a deal with the Philadelphia Phillies.

So what will the Yankees do this offseason? They still need to fill holes in their starting rotation and their bullpen. Cole Hamels and Madison Bumgarner are two free agent starters who could be options for the Yankees. Dellin Betances, Adam Ottavino, and Zach Britton are three free agent relievers who could help solidify the Yankees’ bullpen.

The Yankees have also been linked to several trade targets, including Tampa Bay Rays starter Chris Archer and San Francisco Giants outfielder Andrew McCutchen. It’s still early in the offseason, so the Yankees have plenty of time to make some moves. But it remains to be seen what they will do to improve their team this offseason.

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