ORLANDO — When Brian Cashman struck a deal with free-agent Matt Holliday in December 2016, the New York Yankees GM was about to rappel down a 22-story building while dressed as one of Santa Claus’ elves.

Alongside Saint Nick and Rudolph, Cashman attempted tricks and flips for thousands of families at Landmark Square in Stamford, Conn., all while negotiating a one-year, $13 million deal for his new designated hitter.

That’s the nature of the gig: A trade or signing can materialize at any minute. No flight, family dinner, car ride, relaxing vacation, graduation ceremony, wedding or rappelling spectacle is safe.

“Nothing ever happens in your office,” said Nick Krall, the Cincinnati Reds’ president of baseball operations.

Instead, trades happen from the lobby of the Chicago Theater during a Brett Eldredge Christmas concert (Cubs GM Carter Hawkins), from a lakehouse on a guys’ trip (former Rangers GM Jon Daniels), or in Japan, while scouting a young phenom named Shohei Ohtani (former Reds GM Dick Williams).

Signings happen between performances of “Under The Sea” and “Part of Your World” during a rendition of “The Little Mermaid,” the setting for Cleveland president Chris Antonetti closing a December 2016 deal with free-agent slugger Edwin Encarnacion.

The summer trade deadline breeds desperation and forces activity, so it’s rarely a surprise when a rival executive calls or texts. No GM schedules a snorkeling expedition for, say, July 29.

The offseason is a different beast.

This week, the Winter Meetings are being held in Orlando near the Walt Disney World Resort, a popular spot for activity, and not just because every front-office member is holed up in a suite at the Waldorf Astoria.

Just after New Year’s Day 2017, the Reds signed reliever Drew Storen to a one-year deal. Krall finalized the contract over the phone while wrapping up a safari at Disney’s Animal Kingdom. Three years earlier, as Krall stood in line with his family for 45 minutes to meet Mickey Mouse at the Magic Kingdom, he was on and off the phone hashing out a trade with the Philadelphia Phillies for outfielder Marlon Byrd.

They were five feet from the front of the line when his phone rang one final, critical time. His wife, who affectionately refers to his phone as his “appendage,” said they were not getting out of line. Krall completed the swap of Byrd and cash for pitcher Ben Lively with Mickey within ear(s)shot.

Krall could play Disney World transaction bingo at this point.

“I guarantee I’ve done something at Epcot,” he said.

The front offices for Seattle, Tampa and Cleveland spent a few days under the same roof at Mandalay Bay on the Las Vegas Strip at the 2018 Winter Meetings, yet they didn’t finalize their five-player trade until each party had scattered.

Cleveland’s executives completed their end of the deal from Gate C22 at the airport, near a row of slot machines and a Nathan’s Hot Dogs stand. Then, they lined up in the A1-15 business select boarding group for their Southwest flight home. They claimed seats in the plane’s exit rows and, four hours later, after landing in Cleveland, held a mini press conference at the information kiosk in front of the TSA PreCheck area.

Meanwhile, the Seattle Mariners’ top decision-makers signed off on the transaction — which relocated Edwin Encarnacion, Carlos Santana and Yandy Díaz — from a Las Vegas hospital, where Jerry Dipoto was being treated for blood clots in his lungs.

Technology has turbo-charged the game

The life of a GM has long been frenetic, but it has never been more 24/7.

In March 1992, Indians GM John Hart and Twins GM Andy MacPhail discussed a deal that would send first baseman Paul Sorrento to Cleveland as long as Minnesota’s starter at that position, Kent Hrbek, checked out OK physically.

Hart hauled three hours through Arizona, from Tucson to Yuma, one day that spring — “a long and lonely and desolate trip,” with “tumbleweeds blowing,” he recalled. He pulled off the road in the middle of the desert, stuffed some coins into a payphone and called MacPhail to push the deal to the finish line. Hrbek’s medicals had cleared, and they agreed to announce the trade once Hart arrived in Yuma and could notify his staff.

Coincidentally, Hrbek dislocated his shoulder that day and missed the first couple weeks of the season. Hart believes that if he had waited until he reached Yuma to call MacPhail, the deal would have fallen through.

In January 1996, then-Marlins GM Dave Dombrowski was on his honeymoon at Lizard Island, the outermost island of the Great Barrier Reef in Australia, when his club signed Cuban amateur free agent Liván Hernández to a four-year contract. It was 2:30 a.m. Australian Eastern Standard Time when a final conference call between Dombrowski, Marlins ownership in South Florida and Hernández’s camp in the Dominican Republic was funneled through a switchboard at Dombrowski’s hotel.

Cell phones eventually simplified these processes and turbo-charged the pace of trade activity across the league. No phone booths, no switchboards. Just texting and calling at all hours.

“There’s no time I’m really ever without my phone,” said Guardians president Chris Antonetti. “I’ve tried to get better when I’m at home to separate from it, unless I know we have something going.”

“You’re always on,” said longtime Braves GM Frank Wren.

Sledding hill signings and scuba diving trades

There was a time when executives held a tacit understanding that the last week of the year — a calendar stretch devoted to family and recharging, normally beginning after Christmas — was meant to be a break in the unrelenting action.

“It was kind of a gentleman’s agreement that nobody does anything,” Wren said. “We all need a break. Otherwise, you get zero breaks. As more and more young guys came into the game, they saw that as an opportunity to get an advantage. Pretty soon, we had no breaks, literally getting calls on Christmas Day.”

When Mark Shapiro, now the Blue Jays’ president and CEO, ran Cleveland’s front office, he spent Christmas Eve and Christmas Day in 2004 reworking the free-agent contract for Kevin Millwood, who had issues with his physical. Shapiro was at home in Chagrin Falls, Ohio, and Millwood’s agent, Scott Boras, was vacationing with family in Hawaii, but Shapiro said Boras insisted they finish the deal.

The final week of 2008, the Indians traded for Mark DeRosa, and Shapiro spent Christmas and the ensuing days working out the particulars with the Cubs from the patio of his vacation spot in the Bahamas.

Blue Jays GM Ross Atkins and his family ski in Whistler in British Columbia each December. Atkins was on a ski lift in 2022 when he accepted a call from Kevin Kiermaier’s agent, stuck his phone inside his helmet and closed the deal with the free-agent outfielder.

Wren conducted numerous salary negotiations with agents of arbitration-eligible players during 10- or 15-minute ski lift rides. Derek Falvey negotiated the Twins’ signing of Carlos Correa in January 2023 when he answered Boras’ call from the top of a sledding hill beside his wife and kids.

“It was certainly the coldest negotiation I can remember,” Falvey said.

Wren was on vacation in Cozumel with his family while negotiating a trade with Cashman for pitcher Javier Vazquez in December 2009. Wren was on a boat, in full scuba diving gear, and Cashman said he would assess the Braves’ offer and get back to him. Wren told him he would be diving for the next hour, but during his 45-minute surface interval, they could connect before he plunged back into the water. Sure enough, Wren spent that 45-minute break walking along the beach and finalizing the five-player trade.

A.J. Preller’s parents get poor cell phone reception at their New York home, so when the Padres GM visits them for the holidays, he regularly speeds to a 7-Eleven parking lot about three blocks away. That’s where he set the stage for the acquisitions of Blake Snell, Yu Darvish and Joe Musgrove ahead of the 2021 season.

Hart missed his turkey dinner on Thanksgiving in 1997 because he spent the afternoon in a quiet room in a house full of family as he conversed with Jeff Moorad, the agent for Matt Williams, as the Indians laid the foundation for a trade with the expansion Arizona Diamondbacks.

This is no sob story. It’s just the territory that comes with the job.

“The challenging part,” said former Pittsburgh Pirates GM Neal Huntington, “is how much time executives’ families sacrifice because of potential trades that never come to fruition.”

Atkins and his family were vacationing in Costa Rica last winter when he advanced to the finish line on a deal with free-agent Anthony Santander. Atkins said he can’t afford to “shut it off,” but added, “There’s no one who really complains about that. It’s kind of like being — not as important or impactful as — an on-call surgeon. This comes with it.”

Joked former Orioles GM Dan Duquette: “MLB is a lifestyle choice.”

Swearing your audience to secrecy

Last December, Krall walked out of a Pennsylvania bar, where he was dining with his dad, sister and family, to acquire catcher Jose Trevino from the Yankees. As he finished telling the story of that moment, he answered a call and stepped away.

“I’ve definitely made a trade at a kid’s soccer game,” he said upon returning. “I remember standing there on the phone. You just walk away.”

Then, he took another call.

“You take random phone calls all the time,” he said upon returning again.

Sometimes, you can’t walk away, and you must trust the audience around you.

When the Guardians struck a long-term extension with José Ramírez in April 2022, GM Mike Chernoff joined a conference call with the star third baseman and the organization’s other top officials from an Uber after his flight landed in Cleveland. The Uber driver agreed to keep hush about the conversation he was overhearing.

“Five stars and an extra tip,” Chernoff said.

Huntington only golfed twice a year, always at the Pirates’ charity outings. On multiple occasions, in the midst of 18 holes with strangers, he completed the legwork on a trade. He swore his golfing partners to secrecy until the trade details were public.

There are times executives wish they could walk away — or become invisible.

Cleveland struck early on the trade front in 2002, when the club dealt ace Bartolo Colon to the Montreal Expos for prospects in late June. Antonetti was in the visiting clubhouse at Fenway Park after the team’s game against the Red Sox was rained out, and the news scrolled across the ticker at the bottom of the TV screen for everyone to see.

Antonetti can remember the commentator declaring, “If you’re Jim Thome, you must be thinking you’re next.”

“That was an awkward bus ride back,” Antonetti said.

The scenes they can’t forget

The result of the ever-present chaos is a collection of scenes that stick in the recesses of each executive’s mind.

“I was eating a fish taco at a Padres game,” recalled Jim Bowden, a longtime GM for the Reds and Nationals who now works for The Athletic. Oakland general manager Billy Beane called him one day in May 2007 to suggest a swap of outfielders Ryan Langerhans and Chris Snelling. Bowden accepted the offer on the spot, without a counter.

Cashman and Antonetti completed the bulk of the work on an Andrew Miller trade in July 2016 as a rock climbing instructor belayed Antonetti’s rope at a Pennsylvania resort. In July 2018, Antonetti was on a zip-lining platform in southern Ohio as he neared a deal with Preller and the San Diego Padres for relievers Brad Hand and Adam Cimber.

Bowden was getting a deep tissue massage in November 1998 when he closed a five-player deal that sent Bret Boone to the Braves and landed Denny Neagle in Cincinnati. Bowden was out on his boat with — and trying to motivate, he said — a slumping player in May 1994 when he flipped Roberto Kelly to the Braves for Deion Sanders.

In January 2020, Krall worked toward a free-agent deal with Nick Castellanos while he and his college roommate drove to New Orleans to watch their alma mater, LSU, win the college football national championship.

As the clock ticked toward midnight on New Year’s Eve in 2010, Daniels negotiated the final details of Adrián Beltré’s free-agent contract with Boras while attending a party. They compromised on a sixth guaranteed season in time to watch the ball drop.

There’s often a time crunch, either from an approaching deadline or the fear of another team swooping in. If you don’t answer the call at that moment, will the transaction fizzle?

“That is a very difficult thing to deal with,” Atkins said, “especially when you’re younger in the role, when you’re waiting for the callback. When you put something in someone else’s court and you’re waiting for that return, it feels like you’re paralyzed. You learn how to not put yourself in those positions. How do you keep the leverage? How do you keep the power?”

They maintain control by keeping their phone handy, no matter the situation.

Daniels swapped pitcher Jason Frasor for Kansas City Royals pitcher Spencer Patton while donning a suit at a hotel bar in St. Petersburg, Fla., for his brother’s wedding. Williams spent his cousin’s wedding working on a trade.

The Baltimore Orioles needed catching help in May 2014 when Matt Wieters suffered an elbow injury. GM Dan Duquette finalized a trade with the Padres to acquire Nick Hundley over text from the audience of his son’s graduation from Endicott College in Beverly, Mass. A few minutes after his dad closed the deal, Dana Duquette, later an area scout for the Orioles and Marlins, walked across the stage to retrieve his diploma.

“Nick was a great addition to the team, and he worked closely with (pitching coach) Dave Wallace and led the pitching staff to the 2014 AL East crown,” Duquette said.

“Great family moment.”

— The Athletic’s Dennis Lin and Charlotte Varnes contributed to this reporting.