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There was something about the unsigned e-mail that bothered Brian Cashman -- the unusually sarcastic note hit a nerve when it told the Yankees' general manager "You're no Theo Epstein."

The e-mail didn't stop there: It went on to repeat a familiar second guess in New York this summer, that Cashman was paying the price for signing Andy Pettitte when he could've traded for Johan Santana.

To this, the Yankees executive hit the reply button and returned fire:

"We signed Pettitte and kept our other assets," Cashman wrote. "I'm sorry you were led to believe otherwise."

Finally, it seems, Cashman has a chance for redemption, slim as it might be. The Yankees are on the outskirts of the American League wild-card race, but they begin a three-game series with the Red Sox on Tuesday that could define, once and for all, their enigmatic season.

After a three-game sweep of the Orioles, the Yankees have allowed themselves to dream as long shots. They will have their two best starters pitch in the series against Boston, Pettitte and Mike Mussina, and will avoid seeing Josh Beckett and Daisuke Matsuzaka.

With a five-game deficit in the wild-card race, New York can't afford anything less than taking two of three. But even then, the odds are still hostile. The Bombers have only a .523 winning percentage against teams with better than .500 records, which, as pointed out by WasWatching.com, projects to only a 13-12 finish down the stretch.

Even if the Yankees demolished the weaker clubs, winning six of their remaining seven games, they'd finish with just 89 wins. That's not likely to be enough, given that the Red Sox can finish with 90 wins even if they play out the schedule under .500 (15-17).

Still, the Yankees insist nothing is impossible. Even before the sweep of the Orioles, Cashman said, "We're taking this one game at a time. After everything we've been through, we're still there, and we have a lot of guys who have experience down the stretch."

Yankees officials believe a strong 11th hour is absolutely within the realm of possibility, pointing to their eight-game winning streak after the All-Star break. It seems like a million years ago, but as recently as July 27, the Bombers were just three games behind the Rays and a game behind the Red Sox.

But Joba Chamberlain developed arm trouble not long afterward, and as one member of the organization said, "That totally deflated everyone. That was the straw that broke the camel's back."

Hank Steinbrenner said as much, that an unusual string of injuries ruined New York's chances. But that was before the weekend at Camden Yards, and with it, this week's miniature apocalypse. Johnny Damon spoke for the entire clubhouse Sunday when he said the series "[will] tell us where we are" in the race.

It also will allow the offense an opportunity to continue flexing its muscles; the Yankees are batting .297 in their last eight games. But the recent explosion only deepens the mystery of the summerlong underachievement. This was a lineup that was designed to score 900 runs yet projects to finish with only 758. As the second-guessing continued to swirl around Cashman this summer, his defenders in the organization stake their claim on the following logic:

What difference would Santana have made if the Yankees continue to leave runners in scoring position? Would Santana have been able to correct this team's fatal flaw -- being held to fewer than three runs on 40 occasions this summer, more often than any American League team except the A's?

Last year, the Yankees were held down just 33 times, a disparity so wide it has left team officials without an explanation. Derek Jeter has turned into an extreme ground-ball entity without much power. Alex Rodriguez is having a very good, but not franchise-lifting season -- as he historically has done in the year after winning the MVP award. And there are internal concerns, even after Robinson Cano went 4-for-5 with a game-winning home run against the Orioles on Sunday, that his prolonged underachievement is the byproduct of a four-year, $30 million contract he was awarded this past winter.

The team was convinced that Cano could stay focused despite becoming a multimillionaire at age 25. One team official now admits, "It's possible" the Yankees overestimated Cano's work habits, and underestimated what it would mean for him to lose coach Larry Bowa as a mentor.

In fact, so many of the Yankees' preseason assumptions have failed to materialize that Cashman admits, "Sometimes you do get down" as criticism mounts as it has in August.

"But the idea is to keep moments like that to a minimum," Cashman said. "You're paid to do a job, and you keep moving forward. You just find a way to win that day's game."

Cashman will have a clearer picture of his team's immediate future by the weekend. If the Yankees lose two of three, they can effectively flip the calendar to 2009. Already, the turbo-math says the GM shouldn't hold his breath: CoolStandings.com calculates the Yankees have only a 7.3 percent chance to win the wild card and a 6.2 percent chance of winning the AL East.

Barring a near-miracle finish, the Yankees will be home in October for the first time since 1993, and it's anyone's guess whether Cashman will pay for the lapse with his job.

The Steinbrenner family has made overtures about re-signing the GM, although Cashman's friends say he remains undecided. The executive has displayed hints of a burnout in New York, but he also wants to be proved right about Phil Hughes and Ian Kennedy. Cashman is equally sensitive about his choice of Joe Girardi as Joe Torre's successor.

In fact, one major league executive recently wondered out loud whether the Yankees' inability to hit with runners in scoring position had more to do with Girardi's uptight nature than with the advancing years of their core hitters.

"That's how [the Yankees] miss Torre," he said. "He had the ability to calm everyone down, especially down the stretch."

The anti-Torre elements within the organization dismiss such logic, and, with all due respect to Joe Cool, say he never would've handled this year's bullpen with the same finesse as Girardi.

No New York reliever is on the verge of overexposure, particularly Mariano Rivera, whose tally of 53 appearances places him a mere 22nd in the AL. And therein lies the Yankees' best hope against the Red Sox: When in doubt, Rivera is ready, relatively fresh.

Question is, can the Yankees get him a lead in the next three days?

The answer could go a long way toward clearing up October's crystal ball.

Bob Klapisch is a sports columnist for The Record (N.J.) and a regular contributor to ESPN.com.