The longest-running gripe in baseball is the Yankees have so much cash that only they can afford to bury their mistakes, and since 1998, the still boyish-looking general manager has been the guy wielding the shovel.

Late Sunday night, with New York just 27 outs from winning its 27th World Series—but first since 2000—the small smile that creased Cashman's lips was part relief, part I-told-you-so. It seemed to say, "You have no idea how hard it is to get value for your dollar."

Cashman has shelled out more than $1.6 billion in salaries since a broken-bat single by Arizona's Luis Gonzalez looped lazily over a drawn-in infield and ended the Yankees' last dynastic run as the calendar turned over on a new century.

Since then, he's lavished some of it on ballplayers who were great before they arrived in New York, and a few who were great after they left town. But he conceded that for all the time, research and cash invested in the process, he still hasn't figured out exactly why some thrive there and others leave town with tails tucked between their legs.

And pitchers, he added, remain the most mystifying purchase of all.

"But they're the key to the kingdom," Cashman said. "The last five, six, seven years have proven that beyond a doubt."

The play that put the Yankees back within striking distance of another World Series championship, though, had nothing to with pitching.

No. 2 hitter Johnny Damon singled with two outs and the score tied 4-4 in the top of the ninth of Game 4 off Phillies closer Brad Lidge. On the first pitch to Mark Teixiera, the next hitter, Damon took off for second. When a low throw from catcher Carlos Ruiz briefly handcuffed third baseman Pedro Feliz covering the bag, Damon popped up and alertly took off for third. A double by Alex Rodriguez put New York back in the lead, then Jorge Posada's two-run single provided more room for error than closer Mariano Rivera would need while shutting down the Phillies 1-2-3 to end the game.

The reason the Phillies had no one even close to the base at third on Damon's romp is because they were overshifted on the left side of the infield to deal with Teixiera, a switch-hitter who was batting left-handed against the right-handed Lidge. Few players command that kind of respect, but Teixiera is one of them.

That explains, in part, why the Yankees acquired him before the season and will pay Teixiera an average of $22.5 million this year and for seven more. And after batting in front of Tex and seeing teams employ the shift for an entire season, Damon knew he only needed a moment of daylight to know if the coast would be clear to keep running.

"What I had to see before I could start running to third was how Pedro caught the ball," he said. "So I knew it drug him off some.

"I'm just glad," he added, "that when I started running, I still had some of my young legs behind."

Damon was a star in Boston, but in New York he's just a small piece of the puzzle. He's only the fifth highest-paid position player on their team, but at 35, few clubs could justify paying a player his age the $13 million Damon collects annually in New York. Those same clubs would have to scrimp and save for three years to buy just one player like Teixiera. But he was one of three stars the Yankees added this season—along with staff ace CC Sabathia and No. 2 starter A.J. Burnett—for $423.5 million.

Burnett takes the mound Monday night, like Sabathia a day earlier, on three days' rest. His job is to buy the Yankees bats enough time to build a lead, then turn the game over to the middle relievers and eventually Rivera, arguably the most reliable final act in sports. If Burnett fails, the series shifts back to New York and the Yankees' new $1.5 billion baseball palace for Game 6, where the task falls to Andy Pettitte.

That formula—great starting pitching, timely hitting and Rivera—produced four championships from 1996-2000. Only four players from those teams are still wearing pinstripes—Derek Jeter, Rivera, Posada and Pettitte—and maybe it's just coincidence, but all four bubbled up from within the Yankee organization.

That foundation has given the Yankees the luxury to reload rather than rebuild. There are plenty of players whose skills might earn them a spot on one of the biggest stages in sports, but only a few with the toughness and desire to hold on to their places for long.

Cashman has scanned the globe and spared no expense trying to find them. He knows only too well how rare those guys are. Toward the end of an interview, Rivera's name comes up and the GM's tone shifts almost to reverence.

"A guy we gave very little money to, who came out of a small village in Panama and moved to the big city without ever once stumbling or losing his footing. For him to do what he did for as long as he has," Cashman said, "is incredible."