Of late, Cashman has dealt with more of what he called "pressure" and "mudslinging," knowing the Yankees are weeks away from reporting to Spring Training with a weaker starting rotation than they'd like.
Despite an SI.com report on Wednesday that said the Yankees were prepared to offer Andy Pettitte a $12 million contract to put pinstripes back on, Cashman said that Pettitte still needs to pick up the phone if he's interested in pitching.
"He's made a decision [to retire]. It's just if he changes his mind," Cashman said. "He's decided not to play. If he decides to play, I think that's the rub. The only thing is, I'm left to constantly talk about it because I have to fill a void in the rotation. The obvious area to ask about is Andy Pettitte."
Cashman said that nothing has changed regarding the Yankees' stance on the 38-year-old Pettitte, who they feel has been consistent since the American League Championship Series in telling his team not to expect him to pitch in 2011.
"He's not delaying anything, he's not pushing us back, he's not hurting us," Cashman said. "He was honest up front from the very beginning. Of course we'd like him to play.
"He cares deeply about this franchise, whether it's in 2011 or 2020. He wants us to always win and be successful. He knows he'll always be a Yankee, but whether he decides to pitch again is what's at issue. He has, at this stage, decided not to pitch."
So with nothing hot on the front burner, Cashman instead spent an evening whetting whistles.
Donning the same spiky blond wig he used while rappelling off a Connecticut building last month, Cashman embraced his alter ego for three hours at Foley's New York, with 50 percent of all sales benefiting Ed Randall's Bat For the Cure.
"I've always wanted to be a bartender," Cashman said. "This is my first real gig as a bartender, so I got to fulfill that dream. I've got a dream to win the World Series, and I've got smaller dreams. Tonight I got that out of the way."
Shaun Clancy, the owner of Foley's, said that Cashman expressed an interest in getting behind the bar during an August visit. The restaurant was only too happy to oblige his wishes, with Cashman selecting the charity to benefit.
"We would have liked to have sent him to the Minors for 10 days or two weeks," Clancy said. "His schedule didn't allow it. He's like Robinson Cano -- he's maturing at the Major League level. This is a night shift, not a day shift."
Most of the crowd was pro-Yankees, and Cashman playfully served up a Boston lager to a Red Sox fan by leaving plenty of extra foam. Maybe that was his way of getting even, having earlier admitted that the Yankees' rotation doesn't match up well with their blood rivals at the moment.
"They have a deeper starting rotation right now," Cashman said. "Pitching is the key to the kingdom. I'm not saying they're going to beat us -- we're not conceding anything. But if somebody asked me right now, they might be a finished product, we're an unfinished product. You don't win championships in the winter, you win them in the summer.
"We'll do anything on this club that we have to do when we have to do it. We don't have to do anything right now -- outside of finding starting pitching. I need starting pitching; that's what I need to do."
-- Yankees GM Brian Cashman
"We're looking forward to going head-to-head with everybody and anybody. I'm not taking a back seat to anybody, but at the same time, if somebody wants to ask me about right now -- hey, they've gotten some things accomplished and finished off ahead of us. That's true, but the season hasn't started yet."
Yet Cashman's winter has been an eventful one. Not only did the team engage in a public contract squabble with Derek Jeter, but this week Cashman also voiced an opinion that he would be surprised if Jeter played through the 2014 season at shortstop, believing a move to center field could be in the captain's future.
Cashman said that he spoke with Jeter's agent, Casey Close, to clear up any misunderstandings after those comments.
But he wondered aloud why this was different than any other hypothetical, like when he'd been asked if Joba Chamberlain or Phil Hughes would be Mariano Rivera's heir apparent or, further back, if Randy Johnson could be a serviceable closer.
"I've been in that position before," Cashman said. "For some reason, when that comes around with the shortstop situation, it becomes a really crazy loud story on something that was pure speculation. It's not something we're planning on doing."
Also this week, Cashman acknowledged that Chamberlain's stuff was impacted by a right shoulder injury he suffered in August 2008, explaining why the organization has refused to offer Chamberlain another chance in the starting rotation.
Instead, the Yankees closed a Minor League deal on Wednesday with 37-year-old Bartolo Colon, hoping that he might offer some answers to their starting pitching mix. But as Cashman waved goodbye to his customers at the end of his shift Wednesday, he was well aware that his real work isn't close to done.
"We'll do anything on this club that we have to do when we have to do it," Cashman said. "We don't have to do anything right now -- outside of finding starting pitching. I need starting pitching; that's what I need to do."