What did the Yankees look like the last time they finished under .500?

The Yankees woke up on Thursday with a 60-61 record, the latest they’ve been under .500 in a season in 28 years. If that screams disappointing mediocrity, it’s because the descriptor fits perfectly. There is no other way around it.

For years, even before their run of four World Series in a span of five seasons in the late-1990s, the Yankees have finished with a positive record. They haven’t always made the postseason since the dynasty days were over (missing them in 2008, 2013, 2014, and 2016) but even in those campaigns, their record was above .500. They sold at the Trade Deadline in 2016 and Gary Sánchez almost single-handedly gave them a winning record at 84-78 — their closest brush with a losing record in that span.

The last time the Yankees finished below .500 was in 1992, which was a 36-year-old Buck Showalter’s first managerial season. They had a 76-86 record that year, good enough for fourth (of seven) in the AL East.

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Baseball was, as you probably know, very different back then. The Toronto Blue Jays won their first of two consecutive World Series in 1992, a total of 3,038 homers were hit league-wide (this season, there have been 4,255 with a month and a half left to play), Bobby Bonilla was the highest-paid player, and Barry Bonds still played for the Pittsburgh Pirates, and we were still in an age when relievers were winning the MVP, as Dennis Eckersley took home the honors over Kirby Puckett.

How about the Yankees? Well, those were dark days still. However, 1992 would mark the beginning of the turnaround in many senses for MLB’s most successful franchise. The Yanks hadn’t made the playoffs since their American League pennant in 1981. They had been competitive during Don Mattingly’s MVP peak in the mid-’80s before a string of bad decisions and front office tampering by owner George Steinbrenner sank them to 74-87 by 1989. The following two years were among the worst in franchise history, as Steinbrenner was investigated and suspended for trying to dig up dirt on star Dave Winfield during a feud and New York finished with consecutive 90-loss seasons. They were the AL’s worst team in 1990, and even the No. 1 overall draft pick they “earned” from that feat went bust.

The Yankees were a bit better in 1992. Handed the reins upon Steinbrenner’s ban, GM Gene Michael began to turn the team in the right direction as the retooled the roster and hired his young third-base coach Showalter to oversee the on-field product as manager. They improved by five games and that year actually preceded the first winning season since 1988. New York was starting to become relevant again, in both obvious ways and subtle. They exercised the No. 6 overall pick on an eventual franchise legend in Derek Jeter, saw progress from up-and-coming outfielder Bernie Williams (who improved to a 118 wRC+ as a sophomore), signed swingman specialist Ramiro Mendoza as an amateur free agent, and were pleased when Mike Stanley seized the de factor starting catcher job in the second half with a 152 wRC+ from July onward.

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Another player acquired by trade was Melido Pérez, who believe it or not was the Yankees’ ace in 1992 with a 2.87 ERA in 247.2 innings. That was a career season for him, as injuries and other woes cut him short. Elsewhere on the diamond, Steve Farr converted 30 of 36 save opportunities with a 1.56 ERA as the closer, Danny Tartabull (another offseason acquisition) led the hitters in home runs with 25, and the great Mattingly hit 40 doubles and 14 home runs as he got closer to the end of the line.

With a .272/.322/.384 line, 10 home runs and 28 stolen bases, Roberto Kelly was the Yankees’ lone All-Star representative that year. After the season, Michael would controversially trade him to the Cincinnati Reds for an outfielder who had an off-year in ‘92 after his own All-Star breakout in ‘91: Paul O’Neil, another staple of the late-1990s dynasty.

The O’Neill trade was one of several offseason moves that paid off after the losing record in ‘92. Although they couldn’t reel in top free agents Barry Bonds or Greg Maddux, they did sign future Hall of Famer Wade Boggs, highly-regarded lefty Jimmy Key, and steady southpaw Jim Abbott.

Under Showalter, the Yanks would return to boasting a positive record the next three seasons and broke their playoff drought in ‘95. They lost in the Division Series to Seattle, Showalter was fired, and Michael took a different role in the organization. By the time that the Yankees actually won it all in ‘96 under Joe Torre, the only players on the World Series roster remaining from the losing team in ‘92 were Bernie, catcher Jim Leyritz, and third baseman Charlie Hayes (who had left via the expansion draft and only returned in August of ‘96). Everyone else was brought in from elsewhere or came up through the system.

That’s what baseball and the Yankees were like in the early days of the 1990s, the last time they finished a season with a negative record. They are at risk of returning to that point in 2023 and even if they don’t, they are no longer an AL East powerhouse. New York is last in its division, with all four remaining teams looking better set for the future (and for the present, for that matter). The team missed a chance to start a retooling process at the deadline and while they still have a chance to make the postseason, it’s looking more and more difficult by the day.