Proving successful in at least remaining competitive over a 162-game schedule, the Yankees ultimately have not recaptured former October glories, again bounced from the postseason in the first round in 2007.
Reinforcements in the form of young, high-ceiling talent have sprinkled on the scene, but now the Yankees are at another crossroads. Can they allow this youth to develop into reliable big leaguers or is it time to return to cashing chips for more established personnel?
The latest opportunity to stay with or stray from the course will be presented at the Winter Meetings on Monday in Nashville, Tenn., where the presence of left-handed ace Johan Santana -- among others -- figures to be prominent in the Yankees' minds.
The pathway lining the Twins' suite might well require a velvet rope. This much is clear -- if Santana, a two-time American League Cy Young Award winner is put in play, the Yankees figure to be present.
Santana, who will turn 29 in March, has already made an massive impact, and the Yankees could envision him accomplishing even greater things in New York.
"I love the young kids, all three of them -- I think they have a bright future," said catcher Jorge Posada. "[But] we certainly need a No. 1, and I think that's one of the reasons we are going after Santana. I was really, really impressed with him in the  All-Star Game. I would love to have him.
"It is a need in October, no question about it. When you look at the past World Series champions, they were able to have a No. 1 throw in at least two of the games to win the title."
A complex mix of pure stuff, personality and guile at the front of the rotation, Santana is exactly the kind of player the "old" Yankees would have pursued with double barrels blazing, wielding the talent and bankroll to appease Santana's hovering full no-trade clause.
And as general manager Brian Cashman said earlier this month, despite the re-emphasis on player development, he still presides over the "big-game Yankees ... the Steinbrenner Yankees." The checks can still be written, but at a possible $25 million per year, Santana could prove too pricey even for the Bronx.
Once again, the Yankees figure to lead the Majors in payroll output, especially after committing more than $350 million to retain Alex Rodriguez, Posada and Mariano Rivera -- three members of a roster that have not seen the AL Championship Series since 2004. The Yankees could use a next big surge to get them over the hump.
Part of the Yankees' re-emphasis on young talent was borne out of necessity. Slapping money on the free-agent market like Band-Aids, the Yankees have been burned, gleaning disappointing returns from the likes of Carl Pavano, Jaret Wright and Kevin Brown.
The next generation of front-line pitching could be effective, home-grown and all under 25, a lethal combination. If the Yankees can somehow find a way to keep Joba Chamberlain, Phil Hughes and Ian Kennedy together and healthy, they could be a trio of right-handed arms who can guide the Yankees deeper into October.
"We're doing everything we possibly can to balance both ends of it," Cashman said, "and try to be as self-sufficient as we possibly can, so we're not desperate in the free agent market, and not a team of 25 veterans at all times."
But a smattering of big league innings do not make a career, and until further proven, prospects must remain suspects. Still, new pitching coach Dave Eiland worked with Chamberlain, Hughes and Kennedy down on the farm. Eiland has heard the Santana scuttlebutt, but he sees great things ahead on this course.
"I feel these three guys are going to be mainstays on that Yankees staff for many years to come," Eiland said. "Obviously, you don't rule anything out as far as what you may need to do to put your club in a position to win a world championship.
"Ultimately, if it comes down to having to trade one or two of those guys, who knows? From a personal standpoint, I hope not, but if that makes the club better, then so be it. Just knowing where these three young men stand with this organization, it's not going to be easy to pry any one of those three away from them."
Therein lies the temptation. The Yankees have already declared Chamberlain and second baseman Robinson Cano out of bounds, but with the Twins looking for young, high-ceiling talent, could New York bear to watch one of those pitchers, plus a talented position player like Melky Cabrera, develop in another uniform?
Meanwhile, as new manager Joe Girardi rattled off names for what he envisioned as his potential starting rotation, at least the Yankees could find five men to fill those roles, if needed -- Chien-Ming Wang has won 38 games over the past two seasons, tops in the Majors, and the club insists Mike Mussina still has much to offer despite a down year at 38.
The Yankees could try to unload an outfielder, potentially shopping Johnny Damon or Hideki Matsui, and Girardi has far too many first basemen to promise consistent play. But compared with the moment when he donned a No. 27 jersey at Yankee Stadium and spoke about following his back to the goal, Girardi said securing Posada, Rodriguez and Rivera yields a more positive vibe.
"I think everyone feels better," Girardi said. "When you talk about losing your starting catcher, your starting third baseman and your closer, that's a big concern. It's not like we were losing average players -- we were losing players that were at the top of their profession. Whenever you have a chance to bring them back, it's very exciting."
Still in question is the Yankees' bullpen, which figures to see some turnover even after keeping Rivera in the fold. Though he became the highest-paid closer in the game, agreeing to a three-year, $45 million pact, it wasn't even Rivera's deal that could most impact the Yankees' offseason.
Scott Linebrink's four-year, $19 million deal with the White Sox may have tilted the market for free-agent relievers so greatly, the Yankees may back off pursuits for players like Ron Mahay, a lefty who posted a 2.55 ERA in 67 innings for Texas and Atlanta, or even Luis Vizcaino, who made a career-high 77 appearances out of Joe Torre's bullpen in '07.
With the financial field inflated, the Yankees could find more motivation to continue developing talent from within. Sinkerballer Ross Ohlendorf saw success after moving from the rotation to the bullpen in his first professional season, and Eiland regards Minor Leaguer Steven White as a candidate who could yield similar results in a relief role.
Speaking generally about farm-system development this month, Cashman seemed to have confidence that -- unlike in past seasons -- the Yankees would at least have the option to plug holes from within.
"You always get surprises," Cashman said. "No one had heard of Joba Chamberlain or Ian Kennedy outside of our baseball operations departments.
"Are there other guys that are going to do that and come forward? I don't know. I can't say. We believe we have people who can do that."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.