The Yankees have eight players on their active roster who weren't even born (Anthony Volpe, Ben Rice, Oswaldo Cabrera, Oswald Peraza, Jasson Dominguez, Austin Wells, Will Warren, and Yoendrys Gomez) when general manager Brian Cashman started his tenure on February 3rd, 1998.
Fast forward 27 years to March 29th, 2025, and Cashman is celebrating his 2,500th regular season victory (~92 wins per season).
But it's not all milk and honey for Cashman. The Yankees haven't won a World Series since 2009 and have won just two pennants since 2004 (when Cashman's foolish decision to replace Andy Pettitte with Kevin Brown allowed their rivals, the Red Sox, to break the Curse of the Bambino).
Sure, that might sound great for a team like the Mets, but the Yankees are supposed to be the best team in baseball every year.
Cashman inherited a great team from his predecessor, Gene 'Stick' Michael, and the Steinbrenner family gave him an almost unlimited payroll for most of his tenure. So giving Cashman credit for the Yankee's success between 1998-2001 is like inheriting $999,999 and then bragging about being a millionaire.
Derek Jeter, Jorge Posada, Andy Pettitte, Mariano Rivera, Paul O'Neill, Tino Martinez, Bernie Williams, David Cone, David Wells, Chuck Knoblauch, Scott Brosius are just some of the key members of those teams that Michael acquired as GM. That's why, when looking back and trying to pick out the biggest wins of his career, anything from 1998 to 2001 will be an honorable mention.
Best moments of Yankees general manager Brian Cashman's career
Honorable Mentions:
1998 World Series Game Four. 1999 World Series Game Four. 2000 World Series Game Five. 2001 World Series Game Five.
From 1998 to 2000, the Yankees went 12-1 in the World Series, one of American sports history's most dominant three-year runs. The 1998 team with AL batting champion Bernie Williams, 20-game winner David Cone, future Hall of Famers Derek Jeter, Tim Raines, and Mariano Rivera is quite arguably the best team ever.
In 2001, weeks after 9/11, the Arizona Diamondbacks toppled the dynasty during a World Series where the home team won every game.
Down 2-0 in the series, mystique and aura took center stage, and the Yankees won three straight games. Roger Clemens took the ball in Game 3 and pitched one of the best games in his prolific career.
In Game 4, down by two runs in the bottom of the ninth inning, Tino Martinez ripped a home run to the bleachers in center field, and in extra innings, at the stroke of midnight, Derek Jeter porched one to right field, becoming 'Mister November.'
Game 5 had a similar script to its predecessor, except it was 1998 World Series MVP Scott Brosius who yanked a middle-middle fastball over the wall in left field to tie it in the bottom of the ninth, and newcomer Alfonso Soriano who went the other way and knocked in the winning run in the bottom twelfth with a single.
3. Game 5 2024 ALCS
Facing a 15-year World Series drought, the Yankees, on the brink of winning the pennant, entered the tenth inning tied 2-2 against the Cleveland Guardians.
A key error by usually sure-handed middle-infielder Brayan Rocchio extended the inning, allowing Juan Soto to bat with runners on first and second. Hyperfocused, Soto took a first-pitch ball and fouled off pitch after pitch until Hunter Gaddis challenged him with a 95 mph fastball up in the strike zone that he redirected at 109.7 MPH.
When it landed in the center field stands, 402 feet away, the Yankees were up 5-2 and three outs away from heading back to Fall Classic.
2. Game 7 2003 ALCS
At the time, the Boston Red Sox hadn't won the World Series for 85 years. It wasn't so much a rivalry as a beatdown. But in Game 7 of the 2003 ALCS, they drew first blood, going up 4-0 early and maintaining a 5-2 lead until the bottom of the eighth inning.
Boston had their ace, Pedro Martinez, on the mound, and Yankees first baseman Nick Johnson led off the inning, working the count full but ultimately popping out to second base. Then, Derek Jeter hammered a 0-2 fastball over Trot Nixon's head in right field for a double, and Bernie Williams knocked him in with a line drive to center field, cutting the lead to 5-3.
With arms ready in the bullpen, Red Sox manager Grady Little left the dugout to check on Martinez. Still, Martinez stayed in the game to face Hideki Matsui, who ripped an 0-2 fastball down the line in right field for a ground-rule double, giving the Yankees runners on second and third with only one out. Next Jorge Posada blooped a 2-2 fastball to no man's land between shortstop Nomar Garciaparra, second baseman Todd Walker, and center fielder Johnny Damon, scoring both runners and tying the game. That was it for Martinez, but it was too late for the Red Sox.
The Yankees failed to score Posada from second base, and the game eventually went to extra innings. They only had one man in the bullpen they could trust, Mariano Rivera, and he held the Red Sox scoreless for three innings, throwing 48 pitches and cementing his legacy as the greatest closer in baseball history.
The Red Sox countered with knuckleballer Tim Wakefield, who had a scoreless inning under his belt when Aaron Boone led off the bottom of the eleventh inning. Boone sent the first pitch he saw into the stands in left field, and when he stepped on home plate, the Yankees had stamped their ticket back to the World Series.
1. Game 6 2009 World Series
The Yankees were back in the World Series for the first time since 2003, facing their old friend Pedro Martinez.
In the bottom of the second inning, Hideki Matsui yanked a ball into the second deck just inside the foul pole for a two-run home run. He follows that up in the bottom of the third inning with a two-run single, sending a high fastball back up the middle with the bases loaded.
And then, in the bottom of the fifth, he tagged reliever Chad Durbin for two more runs by launching a ball off the wall in right-center field.
He finished the game with six RBIs and captured the World Series MVP. On the mound, Yankees stalwart Andy Pettitte is the winning pitcher, allowing three runs in 5 and 2/3 innings, with Mariano Rivera getting the last five outs, and John Sterling announcing the Series-clinching call for the fifth and final time of his illustrious career.