Winter is Coming…Who Will Be in Pinstripes When it Ends?

Umpire Mike Winters removes his headset, the thousands of loyal Yankees fans remaining sit quietly, waiting to find out if their season will end. Winters holds up his right arm and closes his fist, indicating that Gleyber Torres did not beat out the throw from Eduardo Nunez, and the Boston Red Sox were advancing. 40,000 groan, Craig Kimbrel breathes a sigh of relief, and the potential series-saving run, Adeiny Hechavarria, returns to the home dugout.

(Photo: Noah K. Murray, USA TODAY Sports)

195 days after a promising Yankees season began, it ended at the hands of the biggest rival in their home. Blame is going around throughout New York, some on Aaron Boone, some on Giancarlo Stanton, really, a little bit on everyone besides Aaron Judge. In the end, though, the Yankees didn’t lose because of a bullpen mistake, they didn’t lose because of a Stanton strikeout, they lost because a superior team just outplayed them.

The long wait to March 28 has begun for Yankee fans, as a new offseason was born the moment Winters made the out call. What will the Yankees do to get to the level of their rivals? Who will come back? What new faces will appear in the Bronx next season? Here’s a way that it could play out.

The Staff

Mike Stobe / Getty Images

Let’s clarify something early, Aaron Boone will be managing the Yankees next season. He made some bad decisions over the course of the year, just like every rookie manager does, but he showed the qualities to be an excellent manager, and Cashman loves him. He will be the 2019 manager. The bulk of Boone’s staff should remain the same, with one exception. 64-year-old pitching coach, Larry Rothschild’s contract, expires this winter. Cashman has been loyal to Rothschild, but his Yankee career could be over. If the Yankees decide to move on, one possible name stands out as an option to replace him: David Cone. If the broadcaster decides he would like to be in the dugout, he should have a variety of suitors. The Yankees make the most sense. Cone has been around the team for years, is friendly with the players, and is a spectacular pitching mind.

UPDATE: George King of the New York Post reports that the Yankees are planning to bring back every member of Aaron Boone’s staff, including Rothschild.

Who’s Under Contract?

The Yankees have just about $96-million guaranteed, before arbitration, to their 2019 roster, $86-million of which is dedicated Giancarlo Stanton, Aroldis Chapman, Masahiro Tanaka, and *gulp* Jacoby Ellsbury for 2019, leaving about $110-million before they hit the $206-million luxury tax that will be implemented next season. It seems that they would like to stay under the tax, but with a chance to improve the roster drastically, don’t be surprised if Hal Steinbrenner does sign off.


Photo Credit: Jim McIsaac

The Yankees have nine arbitration-eligible players on the roster currently, assuming there are no long-term extensions, this seems like a fair prediction:

C Austin Romine — $1,100,000 → $1,750,000

Romine had a career year backing up Gary Sanchez, playing stellar defense while hitting .244 with ten home runs, and earning a relief appearance in the Red Sox 16–1 rout of the Bombers Game 4. This earns him a bit of a raise, but Romine still has to do a lot more to earn starting catcher money.

1B Greg Bird — $582,000 → $1,000,000

Bird gets a raise because everyone gets a raise in his first year of arbitration, but he did not earn it. Bird will have to fight for a spot on the roster next year.

2B Ronald Torreyes — $615,500 → $1,000,000

Fan favorite Ronald Torreyes put together another pretty good year, hitting .280 while somehow only having a .294 on-base percentage. Torreyes is a great depth piece, but another guy that does not have anything close to a guaranteed role on next year’s roster won’t get the biggest cash influx this season.

SS Didi Gregorius — $8,500,000 → $9,250,000

Sir Didi enters his final year of arbitration, coming off of a spectacular year that saw him hit .287 with 26 homers and 87 RBIs while playing Gold Glove defense, all in just 134 games. Didi is already one of the highest paid shortstops in baseball, so his raise won’t be drastic, but the more interesting possibility is if the Dutch shortstop gets a contract extension. Brian Cashman just revealed that Didi would undergo Tommy John surgery in the offseason. The injury could keep Didi out until next summer, and it hurts the chances of an extension getting done this year.

CF Aaron Hicks — $2,825,000 → $4,500,000

Hicks had a downright phenomenal season, both at the plate and in center field. His 4.7 WAR was the second-best among all American League center fielders, behind the unstoppable Mike Trout. This season has earned him a nice raise. Hicks, like Betances and Gregorius, will be a free agent after next season, and many have speculated he could get an extension from the team. Hicks is a great player who is going to be a large part of the 2019 Bombers. However, it will be surprising if he is on the team after next year unless he agrees to a one-year deal for 2020, something not in cards with the money he is going to be in line to acquire. The reason? Estevan Florial. Florial, a soon-to-be 21-year-old center fielder from the Dominican Republic, is the consensus top prospect in the Yankees’ system. Florial is a potential five-tool superstar, and the team has made him untouchable in trade talks. They are serious about him being a part of the future, and it would be surprising if they give Hicks a long-term extension to block Florial.

SP Luis Severino — $604,975 → $4,000,000

Sevy’s final start was embarrassing. After forgetting the time of the game and having a short warmup time, Sevy was tagged for six runs over three-plus innings of work, resulting in a 16–1 loss. Despite all this, Severino undoubtedly earned a large raise from the Bombers. He was the best pitcher of the first half and is an ace. Still 23-years-old, Sevy is the #1 starter for years to come for the Yanks.

SP Sonny Gray — $6,500,000 → TRADED

According to Cashman, Sonny Gray will be traded after a disastrous second season in New York. His contract will most likely come off the books, saving a good amount of money for the Yanks.

RP Dellin Betances — $5,100,000 → $6,500,000

Dellin was untouchable in both the regular season and the playoffs. Betances turned a new page for the Yanks this year, and the team needs to make sure they lock him up long-term as he enters his final contracted season. Betances has closer stuff, but his struggles in that role could steer a team away from giving him closer money. The Yankees however, need to make sure they don’t let anyone else talk to him. When he is on, Betances is one of the best pitchers in the game. Andrew Miller’s contract he signed with the Yankees back in 2015 of 4-years/$36-million could be a good starting point for a possible Betances deal.

RP Tommy Kahnle — $1,312,500 → $1,500,000

Kahnle was one of the biggest parts of the Yankees’ bullpen in 2017, but injuries and a loss of fastball velocity limited him to just 23.1 innings for the Yanks, the majority of which pitched in blowouts. He didn’t do anything to make New York question their decision to send him down, as he pitched to over a six-ERA.

Arbitration $ — $29,500,000

TOTAL Post-Arbitration — $125,500,000

Now it Gets FUN:



It’s finally here. The 2019 free agent class. The greatest of all-time. Well, at least it was supposed to be. The tragic death of Jose Fernandez, the fall-off of Josh Donaldson and Dallas Keuchel, and the lingering injury issues of Clayton Kershaw have taken some of the oomph out of this class, but it remains a great one. Starring Manny Machado, Bryce Harper, Patrick Corbin, and a stacked reliever group, a ton of money will be thrown around this summer. Who could the Yankees target? Here’s a position-by-position breakdown on the Bombers:


The Yankees have refused to give up on Gary Sanchez behind the plate, so any catcher signed would be to compete with Austin Romine. There is only one free agent who could overtake that role from Romine and wouldn’t cost too much: Martin Maldonado. Maldonado is not the best hitter — like Romine — but his arguably the best catcher in baseball behind the plate. Romine’s blocking ability is what makes him good behind the plate, but his arm leaves a lot to be desired. Maldonado has both. When he won the Gold Glove in 2017 with the Los Angeles Angels, Maldonado threw out 39% of attempted base stealers in 138 games, while playing stellar in every other aspect behind the plate. While Maldonado seems like a perfect option, the Yankees will in all likelihood be okay with sticking with Austin Romine for barely a million dollars.

Prediction: Yankees stick with Sanchez/Romine tandem.


The Yankees will undoubtedly sit out on an unflattering first basemen class after Luke Voit burst onto the scene during the last month of the season. The Yankees will either let Voit and Bird compete for the starting spot next spring, or the two will be fighting for a spot on the roster I a different possibility that I’ll get into in a couple of sections.

Prediction: Yankees let the stardom of Chris Carter, Pedro Alvarez, and company go elsewhere.


After Didi Gregorius’s injury, Gleyber Torres could be moved to short, but in this “sim”, Adeiny Hechavarria takes that spot in the mean time. Second base is Gleyber Torres’ spot for years to come. No one gets considered. Tyler Wade and Ronald Torreyes will both compete to be Gleyber’s backup, as the Yankees will let Neil Walker walk (ha) after his up-and-down year.

Prediction: Gleyber Torres and Tyler Wade are the lone middle infielders.


(Photo by Rob Carr/Getty Images)

Everyone skipped directly to this section didn’t they? Miguel Andujar had one of the best rookie years in the history of the New York Yankees and should be the American League Rookie of the Year, but one flaw in his game looms so large that, in Game 4 of the ALDS, with the season on the line, Aaron Boone didn’t trust him enough to put him in the lineup. That’s his fielding. Andujar was the second worst fielder in baseball by the trustworthy stat Defensive Runs Saved. Andujar’s athletic ability and his reaction time was undeniable, but his arm is one of the worst in baseball. He doesn’t have nearly enough range to stay at third, and either cost or came pretty close to costing the Yankees multiple games this season. That is why, despite having the Rookie of the Year at third, Manny Machado will end up in pinstripes. Machado was interested in becoming a Yankee at the trade deadline, and reports say the feeling is mutual. There is one problem with Machado: no one, in the history of baseball, has done more to not get more money while playing great. First, Machado said that he’s “not Johnny Hustle” and never will be. Then, the following game, Machado kicked Brewers’ first baseman Jesus Aguilar’s left foot while it was on first base, in a clearly dirty play. Despite the controversy in Los Angeles, Machado is still a once-in-a-generation talent, with both his glove and bat. Machado may get a long-term deal, but a shorter, high money deal would be smarter. The question is, if Machado comes to New York, what happened to Miguel Andujar? He is either traded, or he’ll learn a new position (first base or left field). Trading him would be shocking, but he could bring back a huge return. The more likely scenario is he moves positions, and the best fit would be left field. Not only is Andujar athletic enough and doesn’t need a great arm in left, but it is the perfect spot for the Yankees specifically. With Brett Gardner and Andrew McCutchen hitting free agency, the Yankees don’t have a left fielder in place for Opening Day. Andujar can be that guy, and if he plays just serviceable defense, his bat will make him one of the best left fielders in the game.

Prediction: The Yankees sign Manny Machado to a 5-year/$200-million deal and move Miguel Andujar to left field.


With the news that Didi will undergo Tommy John Surgery being released, the Yankees will need a shortstop for what could be the better part of the year. Cashman stated at the presser on Oct. 12 that, “We’ll either stay with what we got or we can pursue something stronger.” This could be a sign pointing towards a possible Machado deal, which, in this simulation has already gone down. Machado could man short until Didi returns, but the Yankees should also get an insurance option: Adeiny Hechavarria. Hechavarria is one of the best fielding shortstops in baseball, and, despite being a liability at the plate, was a great find since acquired in a last-minute August 31st deal. Hech should be brought back as a depth and bench option for the Yankees.

Prediction: The Yankees sign Adeiny Hechavarria to a 1-year/$3-million deal


Paul J. Bereswill

Bryce Harper, this time last season, was a lock to end up in pinstripes. Then, the Yankees acquired Giancarlo Stanton last December, halting the Harper plans. The Yankees will probably have to choose between Harper and Machado this offseason, and Machado’s defensive skills give him the edge. One unlikely scenario that could take place is if the Yankees try to shop Giancarlo Stanton. For as much as Yankee fans love to complain about Stanton not being “clutch” or striking out too much, there is no denying he is still an elite player. Stanton proved this during a “down” season that saw him hit 38 home runs and drive in 100 runs. It would be surprising, but if the Yankees find a trade partner (Dodgers?), that would open up Bryce Harper to wind up in pinstripes. In the more likely scenario that Stanton returns next year, Harper could go to the Phillies, Cubs, Dodgers, or any other number of teams. Miguel Andujar was moved to left in this situation, but odds are the Yankees would like to bring in a backup option. Clint Frazier has had the worst luck of any baseball player I’ve ever seen. He’s been blocked for years, then he finally gets a shot with Aaron Judge’s injury, and he gets his second concussion of the year and never returns. A change of scenery that will be brought up later should help Clint, as it seems like his role on this team’s future is not what it was a couple of years ago. With that being said, the backup to Miggy should be Brett Gardner. Gardner had a career-worst season in 2018, but his fielding and leadership ability makes him worth bringing back. His team option is $10-million, which he is nowhere near worth, but if he is willing to take a hometown discount, he could be a nice get.

Prediction: The Yankees move Miguel Andujar to left field, and re-sign Brett Gardner to a 1-year/$5-million deal


Aaron Hicks’s situation was addressed earlier in the arbitration piece about him, but extension or not Hicks will be the everyday center fielder in 2019. No reason to spend any more money, especially with re-signing Brett Gardner to provide outfield depth.

Prediction: No changes in center


Odds are, Giancarlo Stanton returns next year, and he will earn some playing time in right, but most will be as a designated hitter, with superior fielder Aaron Judge manning right for the bulk of the games — barring injury. On the topic of Judge, he is not half bad at the plate either. He missed much time due to a broken wrist last season, which caused to him not reach 30 homers after his 52-homer rookie year. Expect Judge, entering his third full season, to cement himself as a superstar in today’s game.

Prediction: Judge and Stanton split time.


The biggest weakness of the Yankees last season was the starting rotation. There best outing was five innings, one-run from Masahiro Tanaka in Game 2 of the ALDS. No other starter made it past four innings. As of now, the Yankees have just two for sure members of next year’s rotation in-house: Tanaka and Luis Severino. Luckily for them, this is a great free agent class, obviously starring Clayton Kershaw.

Kershaw is likely to exercise his opt-out, and if the Dodgers let him reach the open market, the Yankees need to jump on the opportunity. Kershaw is the single most talented pitcher of this decade, and, despite being just 30-years-old, as already guaranteed himself a spot in the Hall of Fame when he decides to call it quits. The 10-year-veteran hasn’t had an ERA over 2.91 since his rookie season, — when he was 20-years-old — leading the National League in the stat five times over that time frame, earning three Cy Young Awards and being named the NL MVP in 2014. Kershaw does come with his share of complications. The most obvious of which is Kershaw’s injury history. He has missed time due to a back injury in three straight years, having not thrown 200 innings in any one of those years. In today’s game, that’s not needed though. If a team can get 175 innings of Clayton Kershaw, every team in baseball would accept that. Kershaw’s biggest problem, specifically for New York, is his inconsistency in the playoffs. Entering the 2018 NLCS, Kershaw is 8–7 with a 4.08 ERA in his playoff career, including several sixth and seventh innings meltdown. With the bullpen game that is now being played, managers would only need about six from him and could get him out before anything too bad goes down. Kershaw will be the guy, and if the Yankees can get him to agree to a short-term, big money deal, (3-years/$105-million?), he could end up in pinstripes. If I had to bet though, Kershaw will be a Dodger for life, but don’t be expected if the Yankees make a run.

(Photo: Jake Roth/USA TODAY Sports)

This brings up the second best starter on the market: Patrick Corbin. Corbin is undoubtedly the most realistic pitching target for the Yankees. Corbin gushed about one day ending up in pinstripes, telling Bob Nightengale back in March, “It would definitely be great to play there. I are up a Yankee fan. My whole family are Yankee fans. My mom, my dad, my grandpa, everybody. Really, every generation of my family has been Yankee fans.” Corbin’s dream very well could come true this winter, as Jon Heyman reported that the Yankees are expected to target the left-hander in free agency. The team attempted to trade for him before he put together a career year in Arizona, going 11–7 with a 3.15 ERA. These numbers don’t tell the whole story. Corbin has a slider that completely falls off, one of the best pitches in the game, which was the most significant part of him putting together a phenomenal 2018 year. In 2017, Corbin was 14–13 with a 4.03, with a strikeout-percentage of 21.6%. That number jumped to an insane 30.8% this season. Corbin also was able to keep the ball in the ballpark, allowing 15 home runs on a 27.2% fly ball percentage. Corbin would most likely see a little decrease in production, solely from coming into the AL East, but the odds are in favor of Corbin signing with the Yankees before March 28.

After Kershaw and Corbin, the quality and youth of the starters takes a big hit, with the best after these three being Charlie Morton, J.A. Happ, and Dallas Keuchel. All older starters who will most likely get pretty big deals. Happ seems like the most realistic to be a Yankee. In his 11 regular season starts in New York after being acquired at the non-waiver deadline, he was 7–0 with a 2.69 ERA. He was walloped by the Red Sox, but still definitely pitched well enough to earn a big deal.

Photo by Jennifer Stewart/Getty Images

Happ could be brought back but will cost the team a lot. Another option could be the Yankees exploring the trade market. The only prospect that is untouchable in the Yankees’ mind is Estevan Florial, and the team would like to not trade Justus Sheffield, but that seems more realistic as long as the target is controllable. The most apparent trade target is another Diamondback: Robbie Ray. Ray is just 27 and is controlled through the 2020 season. Ray has the stuff of an ace, as seen by his 15–5 2017 season where he also had a 2.89 ERA. He is the kind of guy Brian Cashman dreams about. Young, controlled, and talented. Injuries limited him to an iffy 2018, where he only made 24 starts, but the risk is worth the reward. An Arizona team that is selling off all their pieces could be the team to give the Yankees their Game 4 starter.

The five starter spot has multiple in-house options already to fight for it, in Jonathan Loaisiga, Justus Sheffield, and Chance Adams (Jordan Montgomery is set to miss the majority of the 2019 season). The only guy, the Yankees, could bring in is lovable lefty CC Sabathia. Sabathia didn’t give the Bombers many innings, going just about 5.1 innings per start, but still produced his lowest ERA since 2012. That’s all they need from a five starter. Give CC a new deal, filled with incentives, and have him fight for the fifth starter job with the kids.

Prediction: Yankees sign Patrick Corbin to a 5-year/$120-million deal, sign CC Sabathia to an incentive filled, 1-year/$2-million deal, and acquire Robbie Ray from the Diamondbacks in exchange for Clint Frazier, Albert Abreu, and Domingo German. (May seem a bit pricey, but Ray will be a hot commodity with a high ceiling).


(AP Photo/Julie Jacobson)

The Yankees bullpen was by far their biggest strength in the 2018 season, with Aaron Boone being criticized for not going to his superpower earlier in games three and four of the ALDS. Two intricate pieces from the ‘pen are set to hit free agency this offseason: Zach Britton and David Robertson. Both threw absolute gems to keep the Yankees in the game during game four, with Zach Britton calming down after a leadoff home run. A team is undoubtedly going to give Britton closer money, and it wouldn’t be too smart of the Yankees to shell out that kind of money for a seventh innings guy. That leaves a big hole to be filled in the bullpen, and it should be filled with a familiar face: Andrew Miller. Miller signed with the Yankees in an under-the-radar move in 2015, and it worked out perfectly. Miller dominated in his first year in pinstripes, that brought back a huge return at the 2016 trade deadline. He was arguably the best reliever in the game entering this season, but injuries plagued the 33-year-old, and he only appeared in 37 games, struggling to a 4.24 ERA. Miller lost a good amount of money with that year in his walk year, and the Yankees should take a chance on the lefty with a nearly identical deal to his most recent one.

David Robertson is one of the only Yankees remaining from the 2009 World Series team, and since being brought back by the Yankees at last year’s deadline, has been great. He had an up-and-down season this year, pitching to a 3.23 ERA in 69 outings, and entering his 12th year may be preparing to sign his final contract. The Yankees should show interest, but with the amount of depth in the bullpen of right-handers, Robertson and other righty relievers (Craig Kimbrel, Cody Allen, A.J. Ramos), may get a little too pricey.

Prediction: The Yankees sign Andrew Miller to a 3-year/$36-million deal

Free Agent $ — $92,000,000

Total $ — $217,500,000

What do we got?



2B Gleyber Torres

RF Aaron Judge

CF Aaron Hicks

DH Giancarlo Stanton

3B Manny Machado

LF Miguel Andujar

1B Luke Voit

C Gary Sanchez

SS Adeiny Hechavarria

C Austin Romine

1B Greg Bird

IF Tyler Wade

OF Brett Gardner


1 — Luis Severino

2 — Patrick Corbin

3- Masahiro Tanaka

4 — Robbie Ray

5 — CC Sabathia


RHP — Dellin Betances

RHP — Jonathan Holder

RHP — Chad Green

RHP — Jonathan Loaisiga

LHP — Aroldis Chapman

LHP — Andrew Miller

LHP — Stephen Tarpley

The Yankees do go a little over the luxury tax, but not drastically. Still leaves a little leeway after one of the biggest shopping sprees in a while, something that the Steinbrenners and Brian Cashman need to do, if they want to compete with the Red Sox next year. 


Adam Koplik:

Twitter: @thesportskop

Instagram: @thesportskoppodcast

Podcast: The Sports Kop Podcast

Adam Koplik

Rudy said my bio was too long. Hamilton College '25 Yankees writer, fluent in nerd. Follow me @adamkoplik on Twitter.

Related Articles

Leave a Reply

Back to top button