Past Yankees postseason reboots shows a rollercoaster of highs and lows

The Yankees’ season ended prematurely as the team barely topped .500 and missed the playoffs for the first time since 2016. Fans are not convinced with the promise of rebuilding though Aaron Judge is optimistic about it. Their concerns primarily stem from the history of such rebuilding.

The most positive ones are likely to cite the Yankees reboot in the 2008 offseason. Despite 89 wins in 2008, the Yankees finished third. Meanwhile, Hal Steinbrenner officially became managing general partner in November 2008, spurring another mega-million dollar offseason. Most money went to Mark Teixeira (8 years, $180 million), CC Sabathia (7 years, $161 million), and A.J. Burnett (5 years, $82.5 million).

Despite several key veterans leaving, the Yankees brought back Pettitte and Damaso Marte while a trade for Nick Swisher exceeded expectations. The team went on to win the championship in 2009.

However, the Yankees haven’t reached or won the World Series since 2009, surely on the minds of fans and the club as 2023-2024 begins.

2013 and 2014 overhauls by the Yankees failed

After an 85-win 2013 produced just third place, the Yankees aggressively spent over $500 million in free agency to fill holes. After losing Cano, Mariano Rivera, Pettitte, Granderson, the suspended A-Rod, and others, reinforcements were needed.

Masahiro Tanaka was the biggest and best signing, inking 7-years, $155 million. But Jacoby Ellsbury’s 7-year, $153 million deal proved disastrous. Other major signings included 5-years, $85 million for McCann and 3-years, $45 million for Carlos Beltrán. Jeter and Kuroda got one-year, $10+ million deals, while veterans like Matt Thornton and Brian Roberts signed modest 1-or-2-year pacts. Brett Gardner received a 4-year, $52 million extension.

Despite over half a billion in spending, the Yankees’ 2014 ended prematurely. So lavish 2013-2014 outlays couldn’t quickly restore playoff success. This sparked another rebuilding by the Yankees.

In 2014, the Yankees finished second with 84 wins but missed the playoffs again, their second straight absence. After huge spending the prior offseason, their approach shifted before 2015.

Notable trades occurred, acquiring Didi Gregorius as a substitute for retired Derek Jeter. The Yankees traded Nathan Eovaldi and got Garrett Jones and Domingo German in return. More relievers arrived via trade, but no bullpen boost matched signing Andrew Miller for 4-years, $36 million. Meanwhile, Chase Headley re-signed at 4-years, $52 million. Other veterans were retained with one-year deals.

The Yankees were able to gain a postseason foothold in 2015, only to fall in the Wild Card game to Houston, birthing a lopsided rivalry. So the 2014-2015 offseason featured modest spending, with trades and targeted free agent signings restoring postseason play quickly.

The 2016 offseason approach came as a boost

The last time the Yankees missed the playoffs, in 2016, they went 84-78 and finished fourth. But promising young talents like Gary Sanchez and Aaron Judge offered optimism. Having already traded veterans mid-season, the Yankees continued shedding payroll that offseason when they dealt Brian McCann to Houston.

Aroldis Chapman, one of the vets traded in 2016, returned on a 5-year, $86 million contract, the clear marquee move. Other signings included one-year deals for Matt Holliday and Chris Carter.

Despite a relatively quiet winter, the Yankees returned to the playoffs in 2017, taking the trashcan-banging Astros to Game 7 of the ALCS before a disappointing defeat. So while the 2016-2017 offseason was modest, the emerging Baby Bombers carried the Yankees back to contention quickly.

The road ahead for the Yankees

After the franchise’s worst campaign since 1992, fans expect – or at least hope for – a winter of seismic changes and impactful additions. That ship may have sailed regarding jobs like manager and GM, but the roster still needs serious upgrades across the board.

However, for all those, the organization is likely to again spend big, after a $290 million payroll produced just a fourth-place squad in 2023. After such profound failure, fan pressure mounts for Steinbrenner to rectify flaws through significant expenditure, despite 2023’s lavish outlays gone awry.

Top free agents like Yoshinobu Yamamoto and Cody Bellinger may be available, plus rumors of the Padres’ Juan Soto. But the market is limited, and Steinbrenner has suggested he shouldn’t need a top payroll to win. Money remains the Yankees’ superpower, especially with a flawed roster. Whether they flex that financial might this winter remains uncertain.

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