Despite a wildly successful 103-win regular season, the New York Yankees are heading home for the winter following another disappointingly early postseason exit. The Yankees were eliminated by the Astros on Saturday night in Game 6 of the ALCS (HOU 6, NYY 4). Their 2019 season is over.

"The ultimate pain you can feel in sports," manager Aaron Boone said following Jose Altuve's walk-off homer in Game 6. "Just knowing all that so many put into it, and just know how good of a club we have, to get back into it and then it to end that way. It's hard and our guys are hurting, but I could not be more proud of them and the way they always compete."

Aaron Judge did not mince words after the Game 6 defeat: "It's a failure. 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."  

Two years ago the Yankees reemerged as an MLB powerhouse thanks to a quick-fix rebuild that saw their farm system produce Judge, Gary Sanchez, and Luis Severino, among others, and budding star Gleyber Torres come over in a trade. Shrewd trade pickups like Didi Gregorius, Aaron Hicks, and Luke Voit further bolstered the roster.

The Yankees have won 294 games the last three seasons, third most in baseball behind the Astros (311) and Dodgers (302), yet all three years they failed to win their first American League pennant since 2009. Disappointing exit after disappointing exit:

  • 2017: Lost ALCS in seven games to Astros.
  • 2018: Lost ALDS in four games to rival Red Sox.
  • 2019: Lost ALCS in six games to Astros.

Three postseason exits for three different reasons. In 2017 the Yankees could not muster any offense on the road. They lost all four games in Minute Maid Park and scored a total of three runs. The pitching was a wreck in 2018. Their four starters allowed 15 runs in 13 innings in the four games. This year's ALCS loss was mostly on the offense's inability to hit with men on base.

The Yankees actually out-hit the Astros with runners in scoring position in the ALCS (.171 vs. .109) and won the home run battle (10 vs. 8), but timing is everything. Three of Houston's five hits with runners in scoring position were three run-home runs. Also, the Yankees committed five errors in the six games, and were sloppy overall. Sloppy play equals an ALCS exit.

It can be easy to get tunnel vision after a postseason exit. The reason for the postseason exit is usually evident and the mentality becomes "they need to fix this specific thing in the offseason," and that's not always the case. The Yankees were baseball's best hitting team with runners in scoring position and men on base during the regular season.

Runners in scoring positionMen on base

Batting average

.294 (1st in MLB)

.293 (1st in MLB)

On-base percentage

.371 (4th)

.364 (2nd)

Slugging percentage

.516 (1st)

.518 (2nd)


125 (1st)

124 (t-1st)

The Yankees have talent. Start your lineup with Hicks, Judge, Sanchez, Torres, DJ LeMahieu, and Giancarlo Stanton, and you're doing pretty well. The talent is there and the production in key situations was there throughout the regular season. It wasn't there during a six-game span in the ALCS, and the Yankees are heading home. An overhaul is not needed, just better timing.

What the Yankees do need to get over the hump and back into the World Series is, rather clearly, starting pitching. Their plan to use built-in off-days to rely on the same 4-5 relievers every game backfired when Adam Ottavino turned into a pumpkin and others like Chad Green hit a wall. New York's postseason starters provided no length and strained the bullpen:

  • James Paxton: 13 innings and five runs in three postseason starts
  • Masahiro Tanaka: 16 innings and five runs in three postseason starts
  • Luis Severino: 8 1/3 innings and two runs in two postseason starts

J.A. Happ couldn't keep the ball in the ballpark during the regular season and was one of the last guys out of the bullpen in October. CC Sabathia's knee and shoulder trouble limited him to short relief. Domingo German was placed on administrative leave under MLB's domestic violence policy in September. Gum and duct tape held the rotation together when the postseason rolled around.

Furthermore, the Yankees did not add any pitching at the trade deadline. Not a starter, not a reliever. GM Brian Cashman said the asking prices were too high and he felt getting Severino (and Dellin Betances) back from his injury would be enough to get his team through October. It was a risky move (non-move, really) that blew up in their faces.

Yankees GM Brian Cashman has been unable to add a true No. 1 starter in recent years. USATSI

"It wasn't for a lack of effort," Cashman told reporters, including's Randy Miler, after the trade deadline. "... My job obviously is constantly trying to improve this club and we've been doing it for a long time, and just in terms of the circumstance, we didn't get close to anything. But we certainly knocked on all doors, had a lot of ideas and exchanged ideas with clubs in our effort to improve."

The fact of the matter is the Astros and Nationals will meet in the World Series with No. 3 starters (Zack Greinke and Patrick Corbin) who would have been New York's No. 1 starter this postseason. The World Series will feature three impact starting pitchers the Yankees failed to acquire the last three years:

  • Justin Verlander: Did not claim him on trade waivers in August 2017 because the Yankees were focused on getting under the luxury tax threshold in 2018. (To be fair, no team claimed Verlander, and the Astros traded for him after the fact.)
  • Gerrit Cole: Refused to surrender 2018 AL Rookie of the Year runner-up Miguel Andujar in a trade with the Pirates. Pittsburgh eventually sent Cole to the Astros for a package that looked underwhelming at the time and only looks worse now.
  • Patrick Corbin: Corbin all but shouted from the rooftops that he wanted to play for his hometown-ish Yankees over the winter. They did not want to give him a sixth guaranteed year, so he signed with the Nationals instead.

The starters the Yankees have acquired have underwhelmed. Sonny Gray, for whatever reason, did not mix well with New York and was traded away last winter. He's since blossomed with the Reds. Paxton had a few truly great moments during the regular season, but was mostly inconsistent, and not the impact guy the Yankees envisioned. Happ has been more liability than stabilizer.

With a young position player core in place and nearly all their key late-inning relievers signed or under team control next year, the Yankees figure to again focus on bolstering their rotation this winter. The rotation depth chart heading into the offseason currently looks something like this:

  1. Luis Severino
  2. Masahiro Tanaka
  3. James Paxton
  4. Domingo German (likely to be suspended to begin 2020)
  5. J.A. Happ
  6. Jordan Montgomery (coming back from Tommy John surgery)
  7. Jonathan Loaisiga
  8. Michael King

There is a clear need for another starting pitcher, and room for two new starters. Someone to bump Severino down to No. 2, Tanaka down to No. 3, and Paxton down to No. 4 would be ideal. Someone who can give you 6-7 innings on occasion would be nice too. Only 15 times did a Yankees starter complete seven innings in 2019, the fifth fewest in baseball.

Obviously having a dominant bullpen plays into that -- you don't need to push your starters that deep when you have those relievers ready to roll -- but this postseason is a reminder you have to get some length from your starters, otherwise your relievers will get overworked and overexposed in a hurry in October. The Yankees need to improve their rotation, clearly.

And the Yankees will have an opportunity to improve their rotation this offseason. Cole is scheduled to hit the open market and he will be the best starter to become a free agent since Max Scherzer five years ago. The Yankees made Cole their first round pick in 2008 and couldn't sign him, and they tried to trade for him two years ago. He is Cashman's white whale.

Former Yankees draft Gerrit Cole will be a free agent this offseason. USATSI

Similar to Sabathia in 2008, Cole is close to a perfect fit for the Yankees. They need a high-end starting pitcher and he fits their organizational philosophy as a high-velocity, high-spin, high-strikeout starter. Plus he is only 29, so he's in his prime and he fits the team's win-now window. You could nitpick Corbin as a free agent target last winter. Cole though? No. It's impossible.

Chances are it will require the largest pitching contract in baseball history to sign Cole. David Price currently holds the record at seven years and $217 million, and Cole is a year younger now than Price was when he was a free agent, plus he's coming off a better platform year. Seven years and $35 million annually is not an unreasonable ask for Cole's camp.

The Yankees have the money. Of course they do. The question is whether they're willing to spend it. They ducked under the luxury tax threshold last year, thus resetting their tax rate, and this season they stayed under the second luxury tax tier to avoid escalating penalties. As a repeat offender next year, their tax rate will be even higher.

Next year's luxury tax threshold climbs to $208 million, so the second tier will then be $228 million. Here are the team's current 2020 salary obligations:

  • Guaranteed contracts: $157.2 million (per Cot's Baseball Contracts)
  • Arbitration eligibles: $37.6 million (per MLB Trade Rumors projections)
  • Pre-arbitration eligibles: $5 million (estimate)
  • Miscellaneous: $20 million (estimated player benefits and 40-man roster players in minors)

That adds up to $219.8 million before doing anything this offseason. There's some wiggle room there but, for the most part, the Yankees already have over $210 million in 2020 salary commitments with regards to the luxury tax. Fitting Cole under the $228 million threshold will require serious salary shuffling. (Can the Yankees find a taker for Happ and his $17 million salary?)

There are two x-factors to keep in mind. One, Aroldis Chapman can opt out of his contract this winter. Opting out would free up $17.2 million in payroll space the next two years. It would also leave the Yankees short an elite closer. Plugging Zack Britton into the ninth inning and signing a cheaper setup man is an option. Chapman's opt out is an offseason #thingtowatch.

And two, Tanaka ($22.1 million) and Jacoby Ellsbury ($21.9 million) will come off the books after 2020. The Yankees are one year away from freeing up $44 million in payroll space. For only two players! The Yankees could sign Cole and absorb the luxury tax burden in 2020 knowing relief is coming in 2021 and beyond. Would I bet on it? No. Is it an option? It should be.

Stephen Strasburg could put another elite starting pitcher into the free agent market -- Strasburg can opt out of the final four years and $100 million on his contract this winter -- and second tier options include Madison Bumgarner, Zack Wheeler, and Hyun-Jin Ryu. I'm not sure Ryu will actually leave the Dodgers as a free agent, but who knows. Those are the best non-Cole starters.

The Yankees have tried taking smaller bites with Gray and Paxton in recent years and, after three straight very good but ultimately unsatisfying seasons, it's time for New York to go after the whole pie. Cole will be available for nothing but cash (and a draft pick) and fits their needs perfectly. If the Yankees won't jump back into the deep of the free agent pool now, when will they?