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My Personal Ranking of the Last 4 Yankees Playoff Seasons

By Chris O’Connor, December 2, 2020

This list is purely from an enjoyment perspective and these are my personal thoughts. Preseason expectations were taken into account so that is why teams with worse records may be ranked above better ones.

4th Place. 2020

This was obviously a unique season. Not only was it 60 games, but some gimmicky new rules were implemented like 7 inning doubleheaders and a runner on second base to start extra innings.

For the Yankees, preseason expectations were incredibly high after they brought back nearly everyone from their 103-win 2019 season and added one of the best pitchers in the league in Gerrit Cole. They, along with the Dodgers, were considered the consensus World Series favorites heading into the season and they did not disappoint with a 16-6 start.

The Yankees then immediately went on a frustrating 5-15 tailspin that saw the pitching melt down and the hitters struggle with injuries and inconsistency. The injuries might have been the worst part; after a brutal stretch of injuries in 2019, fans were hoping for better luck with a new training staff. Instead, the injuries continued to devastate the team.

On the pitching side, Luis Severino and Tommy Kanhle missed the year after undergoing Tommy John surgery and James Paxton missed most of the year with various ailments. On the hitting side, the list of who missed time was just as bad, if not worse This list included Aaron Judge, Giancarlo Stanton, Gleyber Torres, DJ LeMahieu, and Gary Sanchez, among others. The next-man up mentality was great to watch in 2019, but by 2020 the injuries were unbelievable and the “next man” didn’t show up as regularly or nearly as often. It may be at a point where the injuries are not just bad luck; the current Yankees might just have an injury-plagued roster

The Wild Card round against Cleveland was fun to watch, but after that first game against Tampa Bay, it was clear that the Yankees were facing an uphill battle.

The only few positives from this season were another playoff berth, Clint Frazier finally getting significant playing time and thriving, seeing Gerrit Cole pitch solid (despite some struggles), and Stanton’s playoff outburst. The core is only getting older, and the World Series drought continues.

3rd Place. 2018

This was a good year for the Yankees. They won 100 games, but it never felt enough for two big reasons.

The first is the shine started to wear off from 2017. Expectations were so high in 2018 after the thrill of shocking the baseball world and ending up just one game shy of a World Series berth, not to mention trading for 2017 NL MVP Giancarlo Stanton. Perhaps expectations were too high because short of a World Series victory, the season was to be considered a disappointment especially after coming so close in 2017.

The second reason is the hated Red Sox. They contrasted the Yankees 9-9 start by winning 17 of their first 19 games and they never slowed down from there. They finished with 108 wins, so though the Yankees won an impressive 100, they were always looking up at their biggest rival. I still remember that early August 4-game series in Boston. The Yanks were 5.5 games back with a chance to cut Boston’s division lead to as low as 1.5 games, but instead the team was swept. In the book Inside the Empire: The True Power Behind the New York Yankees by Bob Klapisch and Paul Solotaroff, an anonymous Yankees player admitted that after that Boston series, the Yankees pretty much knew that it was not their year. From my perspective, I got that feeling as well, but that is still a startling admission from a player on a 100-win team.

On the positive side, Stanton hit two homers on Opening Day against the Blue Jays and after starting 9-9, the Yankees then won 41 of their next 53, a stretch that included Sevy shutting out the Astros while winning 3 out of 4 in a series in Houston.

More Baby Bombers debuted with Gleyber Torres and Miguel Andujar having excellent rookie years highlighted by Gleyber’s walk off home run against the Indians in May and Andujar setting a Yankees rookie record for doubles in a season. Aaron Judge followed up his 2nd place MVP finish in 2017 with a great 2018, though he only played 112 games due to a fluke wrist injury after being hit with a pitch in July. Luke Voit burst onto the scene after a midseason trade with the Cardinals. Luis Severino looked like he was on his way to a Cy Young season until he tanked after the All Star break to the point where he was nearly passed over to start the Wild Card game.

It would have been almost impossible for the Wild Card game against the A’s to live up to the 2017 one, but it came close. Severino pitched four shutout innings, redeeming himself from the 2017 debacle. Judge’s first inning home run electrified the crowd early on and the Yankees never relinquished the lead. Voit’s two-run triple in the eighth inning was also a great highlight.

The Boston series does not need much revisiting. Aside from Masahiro Tanaka in Game 2, the starting pitching was awful. After tying up the series 1-1 going back to New York, Game Three saw one of the worst losses in Yankees history: a 16-1 shellacking that essentially ended the series. Giancarlo Stanton was horrible in this series, flailing countless times in key moments. For many Yankees fans, he still has not made up for it.

2nd Place. 2019

This was a fun, crazy, unexpected year that saw the emergence of many key players but ultimately ended again in disappointment.

The Yankees again got off to a slow start at 6-9 but signaled this year would be different with a quick 2-game sweep of the Red Sox at Yankees Stadium that saw Brett Gardner come through with a huge, go-ahead grand slam late in the second game. The Yanks took the division lead for good on June 14th from the Rays and never looked back.

They played one of the greatest games I have ever seen in a 14-12 win against the first place Twins in July with numerous late lead changes capped off by an Aaron Hicks diving grab in center field with the bases loaded to seal the win.

DJ LeMahieu signed with the team in the offseason and expectations were moderate for him. He did not even start opening day, sitting behind Gleyber at 2nd and Troy Tulowitzki at short, but he ended up finishing fourth in MVP voting. His versatility was made even more valuable when injuries hit this team hard. Giancarlo Stanton and Miguel Andujar combined to play in just 30 games. Aaron Judge missed 60 games, Hicks played in only 59, Luis Severino and Dellin Betances missed virtually the whole year save for a few innings. The Yankees resilience in response to these injuries made the injuries less devastating than they otherwise would have been.

Luke Voit followed his emergence in 2018 with a breakout year in 2019 until a core injury limited him down the stretch. Mike Tauchman, Gio Urshela, Mike Ford, and Cameron Maybin broke out with career years with Urshela in particular emerging as their franchise third baseman. Gleyber Torres hit 38 homers and Gary Sanchez bounced back from an awful 2018 with a good year. The Yankees traded one of their top prospects in Justus Sheffield to get James Paxton, who won 15 games and came up big facing elimination in Game 5 against the Astros. The Twins series was an easy sweep, impressive given how good the Twins were that year. It is easy to overlook that series because of the Yankees dominance over the Twins in the playoffs, but a sweep is a sweep.

The Yankees, however, did not have enough starting pitching against the Astros and timely hitting was nonexistent. Early hooks to their starters in the first five games led to the relief pitchers being prominently used and the Yankees were forced to start a bullpen Game 6. A tired Chad Green gave up three runs in the first inning. The bats, who were quieted all series in a recurring playoff theme, tied up the score with a huge LeMahieu homer in the ninth, but Aroldis Chapman then gave up a walk off homer to Jose Altuve in another heartbreaking playoff loss.

This was a team that absolutely could have won it all. Though the season ended in such difficult fashion, this was a really good, fun team.

1st Place. 2017

Maybe this season spoiled some Yankees fans like me. This team was just so much fun to watch and follow along.

The Yankees had been old, boring, and middling since 2013, and the consensus was, after selling at the 2016 trade deadline, that the team would be rebuilding for a few years. The emergence of the Baby Bombers, however, ensured Yankees fans would not have to wait that long.

Aaron Judge exploded out of the gate for a then rookie record 52 homers, won Rookie of the Year, and came in second in MVP voting to the cheating Jose Altuve. Gary Sanchez followed up his breakout rookie year with 33 homers and an .876 OPS and looked to be the franchise catcher. Luis Severino finally fulfilled his prospect potential with a 2.98 ERA in 31 starts and Aaron Hicks did the same with a .847 OPS and excellent center field defense. This year was so long ago that Jacoby Ellsbury played in 112 games and Greg Bird played a prominent role in the playoffs; his seventh inning homer to break a scoreless tie against Andrew Miller in Game 3 of the ALDS still gives me chills to watch.

The playoffs had too many iconic moments to count: Didi Gregorius’ homer in the wild card game, Bird’s Game 3 homer against the Indians, Didi’s two homers in Game 5 in that series to complete the 2-0 comeback, the Game 4 comeback against the Astros in the ALCS.

More than any one moment, this team was young, exciting, and really seemed to enjoy playing with one another. The past few seasons made me really miss the days of Todd Frazier’s thumbs down celebration and Didi’s exit after 2019 made me appreciate his infectious energy even more. For me, I knew this team was special when they swept the defending champion Cubs at Wrigley Field in early May. This series was highlighted by Brett Gardner’s 2-out, three-run homer in the ninth down 2-0 in Game 1.


Ultimately, these past few years have been filled with plenty of ups and downs. Expectations for this core are intense and it would be incredibly disappointing if they can not win a World Series.

The Yankees’ window is wide open, but with the current core aging and getting closer to free agency, it can close sooner than anyone hopes. Winning with this homegrown core would have a special place in the hearts of fans. Let’s hope that the scars and experiences from these past few years strengthens and motivates the team to succeed in the future.


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