"This is awesome. Going over this building is really cool," said Cashman, appropriately bundled given the weather. "[His kids say], 'You're going to do it again, right, Dad?' 'Yeah!' … I've gotten used to it where I'm not afraid."
Joining Cashman in what has become one of his annual traditions was former big league manager Bobby Valentine, a Stamford native, plus FOX News Channel meteorologist Rick Reichmuth and FOX 5 sports anchor Duke Castiglione.
The group took turns rappelling down one of Stamford's tallest building to prepare for the city's Heights & Lights event, which is meant to celebrate the holiday season and drum up excitement about the downtown Stamford area. Cashman and Valentine will repeat the feat Sunday at 5 p.m. ET.
This time, Cashman will be dressed as an elf.
"You don't know anything for sure," Valentine said, sitting on the edge of the building. "But the odds are with us."
Cashman departed the event before the news and completion of a three-team deal was announced, bringing shortstop Didi Gregorius from Arizona to New York, but the GM took a few moments to discuss the state of the Yankees' offseason activity.
• The club expects left-hander CC Sabathia and righty Masahiro Tanaka to be good to go come Spring Training. Tanaka, according to Cashman, doesn't even have a need to rehab.
"He finished a healthy player, he's returned to Japan and having his normal winter," Cashman said.
Sabathia is spending the winter months rehabbing from his knee issues at Yankee Stadium with Steve Donohue, the team's head athletic trainer.
• Cashman indicated the decision to re-sign righty Esmil Rogers this week was an easy one.
"Good arm. He can start, he can relieve. It's inventory," Cashman said. "He's got great stuff. [Pitching coach] Larry Rothschild obviously likes the player a lot. He knows he's got even more upside with some adjustments."
• The Yankees are open to reuniting with Slade Heathcott on a Minor League deal, according to Cashman. The former first-round Draft pick was non-tendered this week.
• Cashman will leave for the Winter Meetings in San Diego on Monday morning. He expects a flurry of moves across the league during those couple of days, though that's far from a guarantee that the Yankees will be involved.
"It's the industry's way of saying, 'God [darn] it, make a decision,'" Cashman said of the Meetings. "Everybody's had their chances to stare each other down, make their suggestions, turn things down. It's really time to put all the chips in the middle of the table over the next 10 days or wait till Spring Training and go with non-roster invites. That's typically how the industry reacts.
"You'll get a real feel for what rosters will more likely look like by Thursday."