As part of the city's annual Heights and Lights celebration, Cashman, dressed in an elf costume, made the daunting descent from the Landmark building in front of hundreds who braved the cold weather. He wasn't playing the role of Santa Claus, but after the daredevil stunt, some fans couldn't help but take the opportunity to tell Cashman what they wanted for Christmas.
"Bring us Cliff Lee!" one fan yelled in his direction. Several others echoed similar sentiments as Cashman was escorted with Santa and Mrs. Claus to a tree-lighting ceremony down the street.
After Cashman's impressive feat, Yankees fans were already looking ahead to his next: bringing Lee to the Bronx. It's a goal that has Cashman's focus as he heads to Lake Buena Vista, Fla., for baseball's Winter Meetings, which begin on Monday. With the contracts of Jeter and Rivera squared away, his priorities are simple.
"Pitching is everything," he said. "Pitching, pitching, and pitching, so I've been focusing on pitching. I really need to take care of pitching."
No one needed Santa's help to figure out who is at the top of Cashman's pitching wish list. Even though his recent focus has been on completing contracts for his franchise players, Cashman hasn't taken his eye off the left-handed Lee, the biggest jewel on the free-agent market. At this point though, the timetable is mostly in the hands of Lee and his agent, Darek Braunecker, Cashman noted.
"I've been paying attention," he said. "I can't dictate the pace of free agents. ... We have to dance to their dance card."
After months of speculation about Lee's eventual landing spot, talks between the two sides could finally begin to heat up during this week's Meetings.
"We'll be ready to be there and rock-and-roll whenever they say we're ready to talk," Cashman said. "I'll talk whenever he's ready. I'll talk now. I would have talked up on the building if we'd had time."
As it turns out, Cashman didn't have time for negotiations as he rappelled down the building behind "The Grinch," who revealed himself to be a Red Sox fan halfway down. Cashman followed suit, revealing a Yankees jacket under his costume, to the excitement of the crowd below.
While the Grinch donned the colors of the Red Sox on Sunday night, it's the Rangers who are hoping they can steal the show and dash the Yankees' Christmas wish in the weeks to come. The sweepstakes for Lee's services have seemingly become a two-horse race between New York and Texas in recent weeks. Neither side has publicly made an offer to Lee, but recent media reports have suggested the Rangers would prefer not to go beyond a five-year contract, while the Yankees could offer a sixth to seal the deal.
Cashman has already made two trips this offseason to Arkansas to visit the 2008 AL Cy Young Award winner. While those trips would indicate Lee is near the top of the Yankees' priority list, Cashman reinforced Sunday that his courtship of Lee differs greatly from the situation two years ago, when he brought in CC Sabathia. At that point, the team was in need of an ace.
Two years and a World Series title later, it's a different story. For the Yankees, adding Lee represents a "want to, but not have to, because I have a No. 1," Cashman said. "We didn't have a No. 1 before. I'd like to add another one if I could."
Lee is just one of the players Cashman would ideally like to scratch off his wish list in Florida. Monday kicks off what promises to be an intense week of meetings, one which could lead to several free agents coming off the board. Perhaps with added confidence from his latest conquests, Cashman is ready to get started.
"We got a lot more work, to be honest," Cashman said. "That's why I've got to get on a plane tonight. I could have flew tomorrow morning, but I'm going to get down to Orlando tonight because I got to hit the ground running first thing tomorrow."
Bailey Stephens is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.