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  • Former Blue Jays pitcher Ted Lilly opens up about the shocking death of his beloved teammate.
By Stephanie Apstein
November 07, 2017

When most of us heard that Roy Halladay’s plane went down in the Gulf of Mexico on Tuesday, killing the future Hall of Fame pitcher at 40, we wondered: How could this be happening?

Ted Lilly’s reaction was closer to: How could this be happening again?

Lilly had already lost one friend to a small-plane crash. He and Cory Lidle grew close during their half-season together with the 2002 A’s. Lilly went on to the Blue Jays; Lidle spent time with three teams before a deadline trade sent him to the Yankees in ’06. That year Toronto missed the playoffs and New York was eliminated in the first round. Lidle—an amateur pilot—offered Lilly a ride to California, where they both lived in the offseason, in his Cirrus SR-20. Lidle planned to enjoy the trip, maybe make it over several days. Lilly just wanted to get home, so he flew commercial.

The next morning, Lilly walked into his living room and saw it on the news: YANKEES PITCHER CORY LIDLE CRASHES INTO BUILDING IN NEW YORK CITY. Lilly was overcome with emotions—shock, grief, survivor’s guilt—but chief among them was agony for the wife and young son Lidle, 34, had left behind.

“I just kept thinking about the family,” Lilly, 41, says now, and he’s talking about both of them. Lilly mourns for Halladay’s wife, Brandy, and two sons, Ryan and Braden. Halladay was smitten with his family. Normally reserved, he dropped all stoicism for them.

“We’d get back from a road trip and he’d see them and that was about the most emotion you ever saw from Roy Halladay,” says Lilly. “That was the biggest smile.”

According to reports, Halladay was alone this morning when his ICON 5 crashed just north of Tampa. That was rare; he’d spent most of his time with his kids after retiring from baseball in 2013. He had gotten almost everything he’d wanted from the game—two Cy Young awards, one with the Blue Jays and one with the Phillies; eight All-Star selections; a perfect game; a no-hitter in the first playoff game of his career, in ’10, which he’d reached after 12 seasons of making bad teams simply mediocre. (Chillingly, he and Lidle were teammates on the ’03 Jays, a year before Lilly got there.)

“Roy was the most focused, dedicated, hardworking teammate—the most focused, the most dedicated, the most hardworking—that I was ever around,” says Lilly, who pitched for six organizations. He spent three years with Halladay in Toronto in the mid-aughts, where the man Lilly had long admired as an opponent became his good friend.

Philadelphia came within two wins of the World Series in 2010. Halladay never got further, but eventually enough was enough. That glorious right arm hurt, and he missed his family. After that no-hitter—a highlight of his career—he had declined a chance to read the Top 10 list on The Late Show with David Letterman because it was Ryan’s birthday. Halladay signed a one-day contract with Toronto, the team that had signed him as an 18-year-old first-rounder in 1995, and hung it up. He held back tears at his press conference.

Lilly chokes up now. Halladay’s father was a commercial pilot, and Halladay had been passionate about planes as long as Lilly knew him. Halladay’s baseball contracts had forbidden him from getting his pilot’s license, but he liked to get to the Rogers Centre early so he could fly a small remote-controlled plane around the stadium before games. He encouraged Lilly to do the same, then just bought him one himself, even though Lilly never really understood the charm. He mostly derived joy from watching his friend running around on the turf like a little kid, with hours left before he had to get to work. Halladay got his pilot’s license once there was no team to tell him he couldn’t.

“Planes can be an incredible thing, but they’re very dangerous,” says Lilly, his voice thick as he tries to explain what Halladay loved so much up there, and then he’s talking about both of them again. “The freedom of being in the air is probably pretty peaceful.”

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