Meet the Biggest Prankster in Baseball: Yankees G.M. Brian Cashman

Before Game 2 of the 2019 American League Championship Series last October, the Yankees’ third-base coach, Phil Nevin, was sitting at a table in the visiting team’s food room at Minute Maid Park. A clubhouse attendant appeared and told Nevin he had a visitor waiting in the hallway: Alex Cintron, the hitting coach of the Houston Astros.

This was alarming: During Game 1 the day before, the Yankees had shouted angrily at the Astros because they heard whistling coming from the vicinity of the Houston dugout. (This was before the Astros admitted to, and were penalized for, cheating in previous seasons, but opponents had long been suspicious.)

Whether the whistling was simply gamesmanship or something more nefarious, Nevin didn’t like it, or how Cintron was behaving. So he had sent a threat to Cintron — something about meeting anyplace at any time to settle a score — via Astros third baseman Alex Bregman.

But when Nevin burst through the clubhouse doors, Cintron wasn’t there. Instead, it was Yankees Manager Aaron Boone and General Manager Brian Cashman, who was the prank’s mastermind, with cellphones out to capture it on video.

“I couldn’t stop laughing after that,” Cashman said. “When he walked out, he had his game face on.”

For 23 years, Cashman has held one of the most high-profile and demanding jobs in sports: the Yankees’ general manager. In that span — much of it under George Steinbrenner, the exacting and fiery owner who died in 2010 — the Yankees have won 2,131 regular-season games, more than any other franchise in the major leagues; reached the playoffs 19 times, including this year; and claimed four World Series titles, the last coming in 2009, an eternity in the Bronx.

Cashman, 53, is also highly accomplished in another category: pranks. Many inside the Yankees’ organization — from the principal owner, Hal Steinbrenner, George’s son, to the Hall of Fame closer Mariano Rivera — have stories about being on the receiving end of a Cashman practical joke.

“He’s one of the best at it,” said Jim Hendry, the Yankees’ special assistant scout and a former Chicago Cubs general manager.

Reggie Jackson, the Hall of Fame outfielder who is now a Yankees special adviser, added, “He’s always trying something.”

Making personnel decisions for one of the most valuable pro sports franchises in the world can be stressful, and Cashman has used his pranks to defuse tension or produce a few smiles amid it all — especially during a challenging 2020 season complicated by the pandemic.

“It’s just something that feels like it could lighten the load,” Cashman said. “Bottom line: Every day is a day of importance, so any day you can have fun while you’re doing fun work. I just like to have fun.”

Cashman’s mischievous streak dates at least to college, he said. One of the earliest pranks he remembered pulling with the Yankees, with whom he started full time in 1989, came when he was an assistant general manager, a position he held from 1992 to 1998.

From a blocked number, Cashman called one of his mentors and favorite targets, Gene Michael, the former Yankees general manager and manager whose work had laid the foundation for four World Series teams. The Florida Marlins had a managerial opening, so Cashman, disguising his voice and posing as a Miami Herald reporter, told Michael — a scout for the Yankees at the time — that he was on a shortlist for the position.

“Oh man, it was like hook, line and sinker,” Cashman said. “He goes: ‘I certainly can’t comment on that. But off the record, of course I would have interest.’ I started laughing, and he was like: ‘Who is this? Who is this?’ I told him. I was crying because I was laughing so hard.”

Cashman couldn’t recall exactly why he had targeted Michael — probably revenge for a joke Michael had at his expense, he said. Cashman, after all, has pulled so many pranks over the years he can’t remember every one.

“The more august he has gone into his general managership, he doesn’t do those nasty, vicious ones,” said the Yankees assistant general manager Jean Afterman, who added that Cashman has joked with her but “would never dare” prank her, because she could easily get him back.

Afterman, though, has helped Cashman with some of his mischief. Cashman had once been using a cheap machine that produced fake flatulence, and she bought him a higher-quality one she called “the Fartmaster 4000.” (Cashman has burned through many of those.) He hid the device in the visiting players’ lounge at Citizens Bank Park in Philadelphia during the 2009 World Series and watched from an adjacent room.

“In a moment when he felt that everybody was serious, he had the remote in his hand and pushed the button,” said Billy Eppler, a former Yankees assistant general manager who was most recently the Los Angeles Angels’ general manager.

During the 2005 winter meetings, an annual baseball convention, Cashman deployed both a flatulence machine and a little trickery on reporters who were interviewing him in a hotel suite. Cashman intentionally left a piece of paper on a coffee table with a fictional trade proposal with the Milwaukee Brewers that said something along the lines of: “We get Ben Sheets. They get Robinson Cano and Chien-Ming Wang.”

Thinking he had a scoop, Mark Feinsand, who covered the Yankees for MLB.com, placed his notebook on the paper and planned to discreetly follow up with Cashman afterward. “I had to do the big reveal because I didn’t want him to write a false story,” Cashman said.

Cashman has used the fake trade bit on his employees, too. He once changed the contact information in his cellphone for a rival general manager so that he could trick Matt Ferry, the Yankees’ director of baseball operations, into thinking he had completed a trade that Ferry opposed. In reality, Cashman was simply texting himself.

“It’s just naturally part of his personality,” Eppler said. “He just has a really good understanding of tone and timing. He knows there’s times to be serious and times we can laugh a little bit. He understands that’s a good medicine.”

Planning for the annual draft can be one of the more stressful tasks for the Yankees’ front office, said Damon Oppenheimer, the Yankees’ vice president for domestic amateur scouting. But when Cashman arrives every year to the team’s facility in Tampa, Fla., Oppenheimer said, he can put people at ease with his laid-back attire (flip flops, T-shirt and shorts) and his humor.

Around the time of one draft, Oppenheimer said, Cashman used the flatulence machine on him while they were ordering dinner at a restaurant.

“You have to tell the waitress because she’s not going to say anything,” Oppenheimer said, laughing, “but you’re like, ‘This is what we deal with.’”

Cashman said he was fair game for pranks, too. Afterman said she once pranked Cashman years ago with a fake waiver claim for a player who was owed a lot of money.

Phillies Manager Joe Girardi, who was the Yankees’ manager from 2008 to 2017, said he “always” got Cashman back but only vaguely elaborated. “Some of the same things he did to me,” Girardi said.

Pranks have been harder to pull off this season with so many front office staffers working remotely, Cashman said. But recently, when Matt Daley, a director of pro scouting, who lives in New Jersey, went to Yankee Stadium for a meeting held mostly on Zoom to go over the team’s potential playoff opponents, Cashman had a rare in-person target.

So Cashman said he sneaked out of his office and tossed party snaps — the type that make firecracker-like sounds — into the conference room where Daley was sitting during the video call.

Eppler said he had also been the target of party snap blitzes during presentations, as well as a clicker pen that shocks users. Cashman occasionally gave it to him when he was signing official documents.

“I’ve probably forgotten half the stuff I’ve pulled,” Cashman said.

He did remember, though, a few he had inflicted on players. He was the architect behind the drafting of a prank letter from the Internal Revenue Service to Rivera in 2013, the final season of the pitcher’s 19-year career, about a payment owed on behalf of his charity.

“He was so nervous because the number was so astronomical,” Cashman said.

Cashman said he once gave the former outfielder Nick Swisher a prank scratch lottery ticket that produced a $50,000 winner. (He told Swisher he had picked it up at a gas station on the way to Yankee Stadium that day.) Swisher, in the middle of a $27 million contract, raced up and down the hallways in delight at his apparent good fortune.

The instructions on the back read: “Claim forms supplied by Santa Claus. All winning tickets must be validated by the Tooth Fairy and conform to her game rules.” (Cashman keeps these and the party snaps in his office desk.)

As he told his side of Cashman’s prank at the Astros’ ballpark, Nevin insisted he wasn’t looking for a fight with Cintron when he charged through the clubhouse doors last October. He said he expected to have a discussion, “not to knock each other out.”

He still laughs about the practical joke and hinted that he might get Cashman back one day.

“He does a good job of mixing the professionalism with having fun with the guys, staff and players,” Nevin said. “It makes us all better. We all do it in here. It’s nice when your leader is the same kind of personality.”