The day Billy Crystal hit leadoff for the Yanks

January 21st, 2021

If you ask Billy Crystal about his favorite birthday, the answer is easy. How many people get to celebrate another trip around the sun by wearing Yankees pinstripes?

At Derek Jeter’s suggestion, the actor and comedian signed a Minor League contract during Spring Training 2008, when the Yankees granted Crystal one at-bat in a Grapefruit League contest. Crystal was issued uniform No. 60, a nod to the birthday he was about to celebrate.

“I’ve had some great moments in my career, but nothing compares to the fact that I can say, ‘I was the leadoff man for the New York Yankees,’” Crystal once said.

The saga began during a Christmas vacation in 2007, when Crystal and Jeter bumped into each other in the gym of a resort in Costa Rica. Crystal expressed anxiety about his upcoming milestone, and Jeter suggested that he “should do something special” to make it memorable.

A diehard fan who frequently waxes poetic about his first visit to the Stadium, was friends with Mickey Mantle and produced a film about the Bombers’ 1961 season, Crystal suggested that he should get one at-bat in a real game, then announce his retirement and throw the team a party. To Crystal’s delight, Jeter loved the idea.

That was how Crystal landed in the home dugout for a March exhibition against the Pirates, at what was then called Legends Field. With Major League Baseball’s approval, Crystal inked the paperwork to become a Yankee, an act witnessed by Bombers COO Lonn Trost and assistant general manager Jean Afterman.

“The official contract was for $4 million,” Crystal joked in his 2013 autobiography, "Still Foolin’ ‘Em." “But the nice part was that the Yankees gave me three days to come up with the money.”

Taking part in an on-field workout one day prior, Crystal turned double plays alongside Jeter at shortstop, something he’d occasionally been invited to do during the Joe Torre era. Onlookers were impressed when Crystal dug in against guest instructor Tino Martinez, spraying batting practice line drives around the diamond.

It was clear that Crystal had some baseball chops, having once been the senior captain for his high school team on Long Island. To prepare for his greatest role, Crystal held 10 days of workouts with former big league outfielder Reggie Smith, who served as a technical advisor to help actors Thomas Jane and Barry Pepper portray Mantle and Roger Maris in "61*."

Yankees manager Joe Girardi suggested that Crystal should serve as the DH, to which Crystal quipped: “Designated Hebrew?” After batting practice, Crystal munched on peanut butter and jelly sandwiches with Jeter and Jorge Posada, then returned to his locker -- wedged between those assigned to infielder Cody Ransom and pitcher Heath Phillips. He discovered that his shoelaces had been sliced, as well as the toes on his socks. The funnyman tried to take it in stride, recognizing that his new teammates were joshing the oldest rookie in big league history.

Billy Crystal (third from left) stands with Yankees players during the national anthem.

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On the field for the national anthem, Crystal felt a tear roll down his cheek, looking into the packed stands to find his wife, Janice, brothers, Joel and Rip, and daughter, Jenny. Robin Williams was also in the seats, and he remarked that day, “I hope they drug-tested for Maalox.” Mike Mussina retired the side in the first inning, and Crystal walked to the on-deck circle, his boyhood dreams about to be realized.

Jeter patted Crystal’s helmet and told him to “hack.” Left-hander Paul Maholm was the Pirates’ pitcher, then 28 and already a five-year big league veteran. Crystal felt his heart thumping against the "NY" logo on his chest as the first pitch hissed by; a 92 mph fastball, ball one.

“Just try to relax; find something I can touch,” Crystal said. “The first pitch was up, and I could see how fast he was throwing. I thought, ‘All right, I can see it.’ I didn’t feel overwhelmed.”

Maholm challenged Crystal with another heater, this one up and away. Crystal closed his eyes and felt the bat vibrate -- contact! The ball shot past first baseman Adam LaRoche; if it was fair, it could have been extra bases. Alas, the chopper was about three feet foul.

“I thought, ‘Double,’ then I thought, ‘Oh no!’” Crystal later said. “If I get to second, I’d have to stop twice to pee.”

Maholm missed the strike zone with the next two pitches; Crystal’s 5-foot-7 frame didn’t help the left-hander. With the count 3-1, Jeter barked, “Swing! Swing!” Maholm pumped the next pitch past a swinging Crystal to run the count full, then dispatched the actor back to Hollywood with another 88 mph cutter that Crystal waved at.

Crystal asked home-plate umpire Mark Carlson if the last pitch had been a strike; Carlson shook his head. Jeter congratulated Crystal on seeing six pitches, but he was so mad in the moment, Crystal almost missed the ovation from a crowd of 10,705.

“I got very emotional,” Crystal said. “I saw the crowd standing up. I’ve been pretending to be a Yankee since I was 7 or 8 years old. Now I was one.”

Crystal poses with Pirates pitcher Paul Maholm, whom he took his at-bat off of in Spring Training 2008.

Maholm tossed the ball to A-Rod in the Yankees’ dugout. The pitcher later expressed relief that he had not fired a fastball into Crystal’s ribs -- or arguably worse, surrendered a hit.

“I definitely didn’t try to blow it by him,” Maholm said. “It was definitely a little nerve-wracking. I’m glad I didn’t have to watch it every day, him getting a hit off me.”

Still in full uniform, Crystal visited George M. Steinbrenner’s office on the suite level. The Boss hugged Crystal, told him that the fans loved it, then remarked with a straight face: “We’ve traded you for Jerry Seinfeld.” As Crystal packed his bags, he asked a clubhouse attendant who pulled the pregame pranks.

Learning that reliever LaTroy Hawkins had been the chief culprit, Crystal asked how he could return the favor. Within minutes, someone suggested using a power drill to bolt Hawkins’ expensive dress shoes to his locker. Crystal cackled, leaving a souvenir for the veteran hurler: a baseball card autographed with the inscription: “Don’t [mess] with my stuff.”

“It was the greatest thing ever,” Crystal said. “The Oscars, the movies -- those are all great. I’m grateful. But I can always say I led off a game for the Yankees, and that’s phenomenal.”