Where does the Yankees’ current title drought rank in the franchise’s history?

In the midst of their fourth-longest title drought in franchise history, the Yankees are in win-now mode. They’ve taken on the second-highest payroll in the sport, headlined by acquisitions of the game’s top free agent in each of the last two off-seasons in an attempt to bolster their chances of winning a World Series in one of the next couple of seasons.

Though the team’s current run of championship-free baseball is unusual within the franchise’s own history, it’s still above-average when it comes to the rest of the major league landscape. Only eight other franchises have won a championship since the Yankees were last on top, and only 13 have made a World Series more recently.

The Yankees, of course, have lapped the opposition in the long run, appearing in 40 of 116 total World Series and winning 27. The Cardinals have appeared in and won the second-most World Series — 19 and 11, respectively — but still fewer than half of the Yankees’ totals.

If you include their first years as the Highlanders, the Yankees went 20 seasons from their inception until their initial championship in 1923, after losing the Series in the previous two seasons, though only the latter half of those years were under the Yankees name. Before the name change, the Highlanders concluded their ten-year run with 759 losses to 734 wins.

Despite their sub-.500 record, the club employed a handful of eventual Hall of Famers, including workhorse starter Jack Chesbro and diminutive outfielder Willie Keeler. Chesbro’s per-inning statistics pale in comparison to modern stars, but whatever he lacked in all-time firepower he made up for in sheer volume. In 1904, Chesbro led all pitchers in innings (454.2), games (55), starts (51), and wins (41).

Keeler, just 5-foot-4 and 140 pounds, played his best baseball before the turn of the century as a member of the National league’s Baltimore Orioles and Brooklyn Dodgers. Famous for using a preposterously heavy bat for his size, a whopping 46 ounces, Keeler employed supreme bat control to set the all-time record for batting average by a left-handed batter, .424. He was such a pesky out, he earned himself a motto which appropriately described his approach, “Keep your eye on the ball and hit ‘em where they ain’t.”

The two other enshrined Highlanders were both honored for their contributions to the game following the conclusion of their playing careers. Clark Griffith clawed his way to 20 years of pitching experience, but became best known for managing and eventually owning the Washington Senators, whose home stadium bore his name until it fell in 1965.

The final icon on the Highlanders, and perhaps the most central to the tapestry of professional baseball’s first century, was Branch Rickey. Not only did Rickey later invent the modern day farm system of teams owning the rights to their own prospects, disrupting the marketplace of independently owned minor league clubs, he desegregated baseball by promoting Jackie Robinson to the major leagues. In Andy McCue’s excellent bio for the SABR BioProject, he described Rickey’s contradictory nature thusly,

The great decision to break baseball’s policy of excluding blacks, for which he is justly praised, has, in recent decades, tended to overwhelm the highly negative image he had earned before that decision. He went from “El Cheapo” to moral beacon in just a few years, and richly deserved each characterization.

The Yankees’ second title drought, 1963-1976, lasted 14 seasons, but still included three AL pennants. In Mickey Mantle’s waning years, the mid-to-late ‘60s, he was still one of the games’ better hitters, but had lost the mobility necessary to be the same kind of massively impactful starting outfielder he had been for much of the previous dozen or so years. Around him, the stars who’d flanked him in previous championship seasons — Whitey Ford, Roger Maris, Yogi Berra, et al — had faded into obscurity or retired. After winning the 1962 World Series, the Yankees were swept in ‘63, and lost a tough seven-game set to St. Louis in ‘64.

For the next decade-plus, a band of big leaguers highlighted by Bobby Murcer and Mel Stottlemyre maintained mere mediocrity until George Steinbrenner beefed up the club’s arsenal following his purchase of the club in ‘73. With Thurman Munson ascending to greatness, the team acquired Graig Nettles and Willie Randolph via trade, and signed key contributors like Reggie Jackson and Catfish Hunter to big contracts. After losing the World Series in ‘76, the team returned to glory with championships in each of the next two seasons.

Sadly, Munson’s tragic passing combined with the aforementioned stars’ aging to derail the franchise’s momentum. That sent the Yankees into another drought.

This third stretch, the longest in living memory, encompassed teams with a slew of sluggers, but never achieved the depth of production, particularly on the bump outside of Ron Guidry, required to make late postseason runs. Between 1979 and 1990, just five Yankees pitchers earned All-Star nods. For comparison, eight different hitters were named to the game, including perennial honorees like Dave Winfield, Don Mattingly, Rickey Henderson, and Steve Sax. In a different era, this might have been enough to nab a Wild Card spot or two, but because they couldn’t win the division, they missed the playoffs every year for over a decade.

Even in this most recent decade of Yankees baseball, during which they’ve notably lacked consistently elite arms, nine different Yankee pitchers earned a trip to the midsummer classic. The eventual assemblage of homegrown talent — headlined by Derek Jeter, Mariano Rivera, Bernie Williams, Andy Pettitte, and Jorge Posada — helped provide a sturdy foundation atop which the club built championship-caliber baseball for the latter half of the 1990s.

Over the past 11 seasons, the Yankees have recorded a .568 winning percentage, winning the AL East three times. They’ve made the ALCS on four occasions, coming just a single victory away from reaching the World Series as recently as 2017. Their current roster features a number of multiple-time All-Stars, including Aaron Judge, Gary Sánchez, Gleyber Torres, Luis Severino, and Aroldis Chapman.

If the Yankees are to get over the hump with this existing core, it’ll likely have to be in one of the next couple of seasons, before their most expensive players, like Gerrit Cole, DJ LeMahieu, and Giancarlo Stanton, age out of their primes, closing the door on this championship window. If they don’t win in the near future, this relatively short skid could have the potential to challenge the longest in franchise history as their thriving cornerstones age into their twilight years.