And now, they are on the verge of the ultimate payoff for all of their perseverance. The Yankees, who fell to the Angels, 7-6, on Thursday in Game 5 of the American League Championship Series, are one win away from getting back to the World Series for the first time since 2003.
From 1996-2003, the Yankees played in the World Series six times, winning four of them. Posada was a September callup in '96 and wasn't on the postseason roster that year. Other than that, the quartet has been around for every one of those Fall Classics.
For sure, there is a common thread among them.
"They understand what it takes to win," said Yankees manager Joe Girardi. "They have been on very good teams with a lot of talented players. They're extremely talented. They know what it takes when it comes to taking care of their body and being on the field every day, of -- if you're a closer -- being physically healthy year after year after year, taking care of yourself. They understand how to deal with the pressures at this time of the year and not try to do too much."
The run started -- and it's no coincidence -- when Jeter was a rookie. He has embodied what it takes to thrive in October.
"Just try to treat it like any other game," Jeter said. "That's what I try to do. It doesn't mean you're going to succeed. A lot of times, people try to do too much, and it makes things seem bigger than it really is. The consequences are bigger, but it's still baseball. Just try to have fun. To me, it's fun. I like to have fun, and these games are what you play for -- to get the opportunity to play at this time of year."
Pettitte did leave for three years, pitching for the Astros from 2004-06. Other than that, however, these four players have had their fingerprints on every Yankees season for close to a decade and a half.
"It's not easy to be together for so long," Posada said. "Nowadays, having just a couple of guys on the same team [for a long time] is tough. Having four guys together for so long is really unheard of."
"With the exception of Andy leaving for a couple of years, it's kind of hard to believe we've been together for this long," said Jeter. "Fourteen years here, but another two or three in the Minor Leagues."
While CC Sabathia, A.J. Burnett and Mark Teixeira have come in as high-priced free agents and lived up to expectations, the old reliables never go under the radar to their teammates.
"Huge," said Yankees right fielder Nick Swisher. "Those guys define the Yankees. Those guys are just tremendous leaders. They're great role models. Not even the fact that they're great players, because I think their numbers speak for themselves, but just the way the guys are in the clubhouse, the way they carry themselves on and off the field, it's very commendable."
At the age of 35, Jeter was a force this season, hitting .334, belting 212 hits and scoring 107 runs. In the postseason, he is hitting .314 with three homers and five RBIs.
"Well, he's our captain," said Girardi. "Jeet is the type of leader that is going to [speak with players] one-on-one most of the time. He will speak up. We've had our share of discussions where he has spoken up. He plays hard every day, every play. He never takes a play off. He never takes a pitch off.
"Physically, you see him play beat up. You see him play sick. We had to tie him down in the Mets series, he was so sick. He had a 102-, 103-degree fever, and we had to tie him down and say, 'No, you're not playing.' He's still the great leader of this club."
Rivera is considered by some to be the best closer of all time, whether it is regular season or postseason. He has pitched in six of the seven games the Yankees have played this postseason, not allowing a run over 8 2/3 innings.
While most catchers start to break down at the age of 38, Posada was rejuvenated following his right shoulder woes of a year ago. He hit .285 in 111 games, and he is still considered an invaluable presence behind the plate.
The 37-year-old Pettitte logged 194 2/3 innings and won 14 games. He also pitched the clinching victory in Game 3 of the AL Division Series and will take the ball in Game 6 at Yankee Stadium on Saturday, when the Bombers host the Angels at 7:57 p.m. ET on FOX.
Perhaps if the Yankees can finish off the Angels and get to the World Series, the four players who have been together for so long will have a moment together. Or maybe it will be left unsaid.
Though six years between World Series appearances is not a lot for most teams, it can feel like an eternity for players who have been defined by their championships.
"That tells you something -- that it's not easy," said Rivera. "No matter what team you're on, you have to have a special team, special players to get it this far. We have a great team. Whatever we didn't do it in years past, there's no need to talk about that. In 2009, it's a different team. We have a different team every year."
But one thing seems to always stay the same -- Jeter, Rivera, Pettitte and Posada.