This would have been a difficult season for any general manager, losing his prime offseason acquisition to shoulder surgery, his starting left fielder to an elbow injury and his future Hall of Fame closer to a freak knee injury, all within the first month of the season.
But the most difficult baseball season in Brian Cashman's life began back in November, with the most devastating blow of all: the news that his father, John, was suffering from pancreatic cancer.
Now, two weeks after his dad lost the fight that no one ever wins, Brian Cashman faces another October that, because of the expectations laid out by George Steinbrenner and adopted as scripture by much of the Yankees' fan base, at best will end in relief and at worst, in disaster.
The Yankees are on the verge of winning the AL East, and maybe even finishing with the best record in the league if they can take the final two regular-season games against the Boston Red Sox.
And yet, on Monday, his boss, Hal Steinbrenner, had to reconfirm what should have been obvious, that no jobs -- not Joe Girardi's or Randy Levine's and certainly not Cashman's -- would be lost if the Yankees fail to bring home their 28th World Series championship.
No matter what happens in anyone's private world, the Yankees universe always seems to spin on the same axis.
"Is this going to be my toughest year? I don't know," Cashman said Tuesday. "I don't know if all my past experiences are helping me deal with everything now, but you find your motivation where you can."
He was talking about all those years where a Yankees team stumbling to the finish line might well mean a GM on the unemployment line, and anything less than a parade in Lower Manhattan would be viewed as a failure.
These days, Levine, the team president who seems more like the spawn of Steinbrenner than Hal, is the one most likely to use the F-word if the Yankees go out in the first or second round.
Hal seems to understand what Cashman has always known, that once you deliver a baseball team to the postseason, all bets are off. Cashman and Girardi have delivered the team. Now it's up to the players.
"I think we're a championship-caliber team," Cashman said. "But unfortunately, so is everyone who gets in. So we're one of many."
There have been plenty of points in this season when the Yankees have looked anything but championship caliber, such as for most of August and on and off in September, right up until the seventh inning of Sunday's game against the Blue Jays.
"It depends on what snapshot of the season you look at," Cashman said. "Most of it was very good. But there were periods of time when we didn't play very good. This is a team that's capable of great things but at the same time, it's a sport, if you don't play at your best you're also capable of some bad things, too."
But Cashman senses that fortunes are starting to turn at the right time for his club. He ticked off what he thinks a baseball team needs to be successful at this time of year: "You gotta be talented. We are that. You gotta be healthy. We're getting there. And you gotta be lucky."
That part remains to be seen. From the first day of spring training, when Michael Pineda showed up in camp admittedly 10 pounds overweight, luck hasn't always been with these Yankees.
Pineda never did get untracked in spring training, barely breaking 90 on the gun, and he eventually needed rotator cuff surgery. Brett Gardner dived for a ball in early April and didn't get back up until this week. Mariano Rivera stumbled shagging flies in the outfield in Kansas City in May and was lost for the season.
All the while, Cashman's attentions were divided between New York and West Palm Beach, where his dad was waging a battle he ultimately could not win.
Through it all, father and son bonded the way many fathers and sons have always bonded, through baseball.
"While my dad was struggling and going through this stuff, the Yankees were always something he could look forward to," Cashman said. "That's what we talked about. 'What time is the game on today? What time is the game on tonight?' It kept him going."
And the memory of John Cashman, and how much joy another Yankees World Series title would have brought him, is what is keeping Brian Cashman going now.
"Just like you know other people are living and dying with us, you know these games are important to your family members, too," he said.
Cashman said since his father's death, the games have taken on an added importance for his mom, Nancy. It's almost as if the Yankees are keeping alive her connection to the man she was married to for more than a half-century.
"Now that he's gone, my mom tapes the games every night," he said. "And if she falls asleep during it, in the morning she wakes up and watches it."
So even if this October is no tougher than all those that came before it, it certainly is different, in terms of motivation. Brian Cashman's job isn't at stake here, nor should it be.
"I always want to win, but I want to win for a lot of reasons this year," he said. "For my myself, for my family, for my mom, for my dad in heaven, and for my job because it's my responsibility to Hal. I just keep thinking that maybe if we win, it will give my mom some joy and happiness."
And in some way, he hopes, do the same for another Yankees fan who won't be here to see it.