The 2019 season played out like the 2017-18 seasons for the New York Yankees. They were one of the game's best teams during the regular season, going 103-59 despite a barrage of injuries, yet they fell short of their ultimate goal, which is a World Series parade down the Canyon of Heroes. New York was eliminated by the Astros in the ALCS for the second time in three years.

"It's a failure," Aaron Judge said about the season following the team's ALCS Game 6 defeat. "In spring training we talked about winning the division, putting ourselves in a good spot in the postseason and the World Series, and we came up short. So no matter how many games we won in the regular season or anything else we did, the season's a failure."  

When a team as good as the Yankees doesn't win a World Series title, it can be easy to think drastic changes are required to get over the hump. Just ask those recent Dodgers teams. In reality, the Yankees will bring back nearly their entire core next season -- Brett Gardner and Didi Gregorius are their most notable free agents -- and they need tweaks more than an overhaul.

That said, the Yankees do have one glaring need heading into the 2019-20 offseason, something they seem likely to address one way or another. Here is a primer on New York's offseason situation.

Payroll situation

The Yankees lowered payroll in order to get under the luxury tax threshold in 2018 and raised payroll back to its previous levels in 2019. Their $218 million payroll this past season was third highest in baseball behind the Red Sox ($229 million) and Cubs ($218 million) and right in line with their 2007-17 payrolls. Payroll has remained mostly stagnant in the Bronx despite rising revenues.

Here is what New York has on the books heading into 2020:

Add in the $15 million or so each team must contribute toward player benefits -- the benefits count against the luxury tax payroll -- plus salaries for pre-arbitration players and the rest of the 40-man roster, and the Yankees already have about $210 million on the books for 2020. Judge and Gary Sanchez are starting to make real money through arbitration. No longer are they dirt cheap pre-arbitration players making close to the league minimum.

The luxury tax threshold is $208 million in 2020 and the second luxury tax tier, which kicks in additional penalties, is $228 million. There were indications throughout the 2019 season that owner Hal Steinbrenner did not want to exceed the second luxury tax tier and incur those additional penalties. Until they show otherwise, I think we have to assume the same will be true in 2020.

It is worth noting the big contracts belonging to Masahiro Tanaka ($22.1 million annually) and Jacoby Ellsbury ($21.9 million annually) are set to expire following next season. The Yankees could choose to exceed the second luxury tax (or even the third tier at $248 million) next year knowing relief is coming after the season. We'll see.

Biggest needs

usatsi-134783771.jpg
Aroldis Chapman's extension answers one question for the Yankees this offseason. USATSI

The Yankees handled one major piece of offseason business over the weekend when they signed closer Aroldis Chapman a one-year extension to avoid his opt out clause. He is now under contract through 2022. Had Chapman opted out, the Yankees likely would have had to bolster their bullpen in some way, even if they could have easily slid Zack Britton into the closer's role.

Anyway, the Yankees have one glaring need this offseason: starting pitching. It is not the reason they lost the ALCS -- New York's starters had a 3.29 ERA in October, nearly identical to the Astros (3.30 ERA) -- but it certainly contributed to the early postseason exit. The Yankees had to start a gassed Chad Green as an opener in Game 6 because they lacked a fourth starter, remember.

Here is New York's rotation depth chart at the moment:

  1. Luis Severino (missed the first 5 1/2 months of 2019 with shoulder and lat injuries)
  2. James Paxton
  3. Masahiro Tanaka
  4. Domingo German (expected to serve a suspension under MLB's domestic violence policy)
  5. J.A. Happ
  6. Jordan Montgomery (missed the first 5 1/2 months of 2019 while rehabbing from Tommy John surgery)
  7. Jonathan Loaisiga
  8. Michael King

Happ allowed 34 home runs and pitched to a 4.91 ERA this past season. Could he be better with a potentially un-juiced baseball in 2020? Sure. Should the Yankees count on that? Nah. The Yankees have a clear need for another starting pitcher and not just a back-end innings guy. Someone to push Severino down to No. 2, Paxton to No. 3, Tanaka to No. 4, and so on.

For what it's worth, here's what Steinbrenner told Dan Martin of the New York Post about his team's rotation last week:

"If the 2020 season was to start tomorrow, I would feel considerably more confident than I did a year ago at this time,'' Steinbrenner said. "We will have both Severino and Montgomery back. We now know that [Domingo] German can pitch effectively at this level. And we know [James] Paxton can be the guy that we were hoping for when we made that trade. We have [Masahiro] Tanaka, [J.A.] Happ, [Jonathan] Loaisiga, and perhaps [Deivi] Garcia at some point. A very good rotation.'' 

The Yankees were always going to say that. There's no reason to show your cards this early into the offseason. All that would do is hurt their leverage in contract talks. Remember though, the Yankees said something similar at the trade deadline, and they stood pat. Something similar could happen this winter. Either way, the Yankees need another starter. 

In addition to another starting pitcher or two, the Yankees also need a center fielder for at least a few months while Aaron Hicks works his way back from Tommy John surgery, and possibly a backup catcher to replace free agent Austin Romine. Otherwise the Yankees are fairly set because they can slide Gleyber Torres to shortstop and install DJ LeMahieu at second base full-time to replace Gregorius. A starter should be priorities one, two, and three this winter. Then it's a center fielder and general depth.

Trade chips

Back in August, Baseball America ranked the Yankees farm system 21st in baseball. They don't have a truly elite prospect to offer in trades -- top prospect Deivi Garcia is very good but not among the game's best prospects -- and many of their best prospects are in the lower levels of the farm system. Those guys usually don't headline trade packages for impact players. They're usually second or third pieces in a trade package.

New York's best trade chips are on the MLB roster. It's Clint Frazier, who has seemingly fallen out of favor in the organization. It's Miguel Andujar, who missed pretty much the entire 2019 season following shoulder surgery. It's young infielders Thairo Estrada and Tyler Wade, who have MLB experience but are essentially prospects. It could be Montgomery as well. Would the Yankees trade a promising young starter coming off elbow reconstruction for more of a sure thing? It's possible.

In an effort to create payroll space, the Yankees could try to move Happ in a salary dump trade similar to their A.J. Burnett (to the Pirates in 2012) and Chase Headley (to the Padres in 2017) salary dumps in recent years. The Angels and Phillies pursued Happ as a free agent and maybe they have interest in him now. Happ is owed $17 million next season, and while the Yankees aren't in position to give away rotation depth, it is money that can be better spent elsewhere.

The Yankees are almost certainly not going to trade Torres, so their best trade chips are good but not great prospects, a seemingly out of favor outfielder, an injured third baseman, and some miscellaneous pieces. That could put them at a disadvantage in trade talks this winter. How are they supposed to outbid teams for, say, Francisco Lindor? Realistically, New York's best trade chip is money. Trade money for free agents.

Possible targets

usatsi-135194421.jpg
Gerrit Cole should be the Yankees' No. 1 target this offseason. USATSI

Let's handle the easy stuff first: Gardner is almost certain to return in 2020. He would play center field while Hicks rehabs before sliding over to left field or into a fourth outfielder's role depending on his production. Gardner is the longest tenured Yankee, he is still productive, he is beloved in the clubhouse, and he fills an obvious need. A deal figures to come together quickly.

As for the rotation, the Yankees should -- should -- be looking at the top of the free agent market. Here are the top free agent starting pitchers according to our R.J. Anderson:

  1. Gerrit Cole
  2. Stephen Strasburg (opted out over the weekend)
  3. Madison Bumgarner
  4. Zack Wheeler
  5. Hyun-Jin Ryu

Cole and Strasburg are elite starters and in their own little tier this offseason. I'd argue Cole is in his own tier even above Strasburg, but that's another topic for another time. Bumgarner, Wheeler, and Ryu are in the next tier, then there's a bit of a drop off to the next tier (Cole Hamels, Dallas Keuchel, Jake Odorizzi, etc.).

The Yankees drafted Cole in the first round back in 2008 and they tried to trade for him two years ago, and they failed to acquired him both times. Cole went to UCLA rather than turn pro in 2008, and of course the Pirates traded him to the Astros in 2017. Cole is GM Brian Cashman's white whale. Will they let him get away a third time? Ownership's payroll mandate may dictate that answer. It would be awfully tough squeezing a $35 million per year contract under the second luxury tax tier.

The trade market could offer some intriguing names as well. Will the Mets make Noah Syndergaard available (again), and, if they do, would they actually trade him to the Yankees? Corey Kluber could be on the move in a cost-cutting move given the young arms who stepped up in Cleveland this year. The Diamondbacks listened to offers for Robbie Ray at the deadline and could again.


For the Yankees, the offseason plan seems very simple: throw money at Cole, and if that fails, go after Strasburg or Bumgarner or Wheeler. Add that high-end starter to 2019's highest scoring offense and a powerhouse bullpen, and try to get over the hump in 2020. It's not easy to improve a 103-win team that has its young core in place, but the Yankees have an obvious path to do it.