NEW YORK -- With 27 World Series championships, any list constrained to the five best seasons in Yankees history is incomplete by definition. It’s an impossible task, one destined to leave behind years deeply imprinted in the hearts of fans.
Still, we’ll attempt it here. The most fair approach may be to sort by regular-season victories -- recognizing, of course, that more recent pinstriped clubs had a slightly longer schedule. With that caveat, here are the five winningest teams the Yankees have fielded:
1998 Yankees: 114 wins (won World Series vs. Padres)
The ’98 Yankees were one of baseball’s most complete teams, steamrolling opponents to a since-surpassed American League record for regular-season victories, then stomping out 11 postseason wins as they claimed the franchise’s 24th World Series trophy in a sweep.
That happy ending was not evident in April. In turmoil after losing four of their first five games, manager Joe Torre was already reported to be on the hot seat, prompting a pivotal meeting before a Tuesday-evening contest at the old Seattle Kingdome. Torre talked, players talked, and the season was back on track.
Derek Jeter, Paul O’Neill, Bernie Williams, Scott Brosius, Tino Martinez and Chuck Knoblauch powered a balanced lineup. Darryl Strawberry, Tim Raines and Shane Spencer gave depth. David Wells, David Cone, Andy Pettitte and Orlando Hernandez headed a strong rotation, with Mariano Rivera and others waiting in the bullpen. These Yankees excelled in every facet.
“Literally every day we'd come to the ballpark and be like, 'We're going to win today,'" Pettitte said. "You don't always have that. It was like, no matter what happened, it seemed we were going to overcome that. We were going to win. It was just a great team."
1927 Yankees: 110 wins (won World Series vs. Pirates)
The “Murderer’s Row” Yankees of Babe Ruth and Lou Gehrig remain shorthand for dominance and intimidation, with seven future Hall of Famers in uniform as they finished 19 games ahead of the second-place Philadelphia Athletics while leading the AL from wire to wire.
With the pennant a foregone conclusion, the first great home run chase captured fans’ attention, with Ruth and Gehrig pushing each other. A torrid September catapulted the Babe to 60, while the AL MVP Gehrig finished with 47. Their 107 combined homers were more than any other AL club.
Earle Combs, Bob Meusel and Tony Lazzeri kept the lineup humming, and New York outscored opponents by 376 runs. It wasn’t just brute force. Waite Hoyt had the best season of his career, going 22-7 with a 2.64 ERA. Herb Pennock, Urban Shocker and relief ace Wilcy Moore also shut down the league.
1961 Yankees: 109 wins (won World Series vs. Reds)
The home run chase between Roger Maris and Mickey Mantle sparked a summer’s worth of headlines, pursuing Ruth’s decades-old record for home runs in a single season. Maris finished with 61, Mantle with 54, and the myriad controversies gave Billy Crystal grist for his excellent 61* project years later.
But the ’61 Yankees were more than the M&M Boys. They reeled off a 13-game winning streak in September to put the pennant on ice, finishing eight games ahead of the Tigers. Elston Howard starred behind the plate, with thump added by Moose Skowron, Yogi Berra, and super-sub Johnny Blanchard.
Cy Young Award winner Whitey Ford had a career year, going 25-4 with a 3.21 ERA atop the rotation while leading the league with 283 innings. Bill Stafford, Ralph Terry, Rollie Sheldon and Luis Arroyo also played key roles in delivering the franchise’s 19th championship.
1932 Yankees: 107 wins (won World Series vs. Cubs)
Nearly a century later, fans still debate Ruth’s actions in the fifth inning of Game 3 during the 1932 World Series at Wrigley Field. Ruth certainly pointed at something. Whether he promised a home run or simply chastised a crowing Cubs bench, he then delivered a towering blast off Charlie Root.
Either way, it was the defining moment of a Yankees season under manager Joe McCarthy, in which the aging but formidable Ruth continued his on-field partnership with the dominant Gehrig. New York finished 13 games ahead of Philadelphia, with Combs and Lazzeri again playing prominent roles.
Lefty Gomez paced the club with 24 wins, but Red Ruffing had the better overall season, going 18-7 with a 3.09 ERA in 35 games. The ’32 Yankees were the first team in Major League history to go an entire season without being shut out.
1939 Yankees: 106 wins (won World Series vs. Reds)
In a season that opened with an ailing Gehrig removing himself from the lineup after 2,130 consecutive games, the Yankees overwhelmed opponents with flawless execution and balance on both sides of the ball.
Powered by standout Joe DiMaggio, who earned his “Yankee Clipper” nickname that summer, New York won 28 of 32 games from May into June to make the pennant a near certainty. The Yankees scored 967 runs and allowed just 556, producing a +411 run differential that remains a Modern Era record.
Gehrig delivered his “Luckiest Man” speech on July 4 at Yankee Stadium, before a roster that included Bill Dickey, Red Rolfe, Joe Gordon, Charlie Keller and George Selkirk. Ruffing went 21–7 with a 2.93 ERA despite an ailing arm, while Gomez finished 12-8 with a 3.41 ERA.