The night before Roy Halladay died, he was with his team. It was Nov. 6, 2017, and Calvary Christian High School was playing an exhibition game in Clearwater, Fla.
Halladay, a pitching coach, showed up in baseball pants and a batting practice jacket, with a clipboard beneath his arm. This would not have been unusual for March or April, but fall ball was much more relaxed.
The rest of the staff, which was dressed in shorts and T-shirts, erupted in laughter. Halladay didn’t hesitate to fire back. “Thanks for the heads up,” he said with a grin.
As the Warriors jogged onto the field, just past 7 p.m., the future Hall of Famer sat on the bench. After a few innings, infielder Christian Cairo joined him.
He liked watching games with Halladay. The former Phillie and Blue Jay brought the same intensity to coaching that he did to his 16-year MLB playing career, but with a newfound lightness.
He’d routinely crack jokes from the dugout. Months earlier, a hitter from a local high school walked up to the plate. He had straight, long hair, all the way down to his back. Halladay turned to the mound.
“Hey!” he yelled. “Look out for the bunt! This chick can run!”
The high schoolers loved it.
“Ridiculous stuff like that,” said Halladay’s 25-year-old son, Braden. “It was funny because he’s saying this to, like, 14-year-old kids.”
Halladay was in prime form on Nov. 6. The game wouldn’t count toward Calvary Christian’s record, but he was still taking notes and videos on his iPad.
He was also razzing everyone in sight: his players, their players, umpires.
“We were talking crap with each other,” Cairo said. “It was a lot of fun.”
At 9:30 p.m., the two teams left the field. By the next afternoon, ominous rumors had started to spread. Braden, then 17, got a call from his mother. She told him to pick up his 13-year-old brother, Ryan, and drive them to their house.
Pitcher Nolan Hudi texted Braden while he was in the car. He sent a link to a Twitter post: a selfie of him and Roy in the cockpit of his plane, taken three days prior.
The photo had gone viral. People were commenting “RIP.”
Hudi asked if people on social media had ever tweeted such morbid things about his father.
“No,” Braden said.
That morning, at 11:47 a.m., Halladay had flown his Icon A5 out of Brooksville-Tampa Bay Regional Airport. A few minutes after taking off, he crashed into the Gulf of Mexico.
An autopsy showed he’d had amphetamine and morphine in his system, and a federal investigation into the crash found he was flying dangerously. He died of blunt force trauma and drowning. Halladay was 40.
The boys he coached are now men. Braden works in data analytics for the Texas Rangers. Cairo, 25, is a minor leaguer in the Phillies system. Some have played for other affiliates; Hudi spent a couple of years pitching at the University of South Florida.
They all cherish that 2017 season. Not just for what they learned (which was plenty) but for what they saw. As a big leaguer, Halladay was fierce and, at times, intimidating.
But as a coach, he was more laid back. He’d play pranks. He’d chirp. He’d try goofy things to help his team win, like flying a drone over a rival’s batting practice.
It was all refreshingly fun. What the players didn’t realize, though, was that they were giving Halladay something too.
“A way for him to enjoy baseball,” Braden said, “in a very pure form again.”
Roy being Roy
Halladay never liked the spectacle his success could bring. And it was difficult for him to escape.
His sons started playing travel ball in the early 2010s, at the height of his career. The Phillie would frequently be stopped for autographs at games and tournaments.
This attention got so bad that he started keeping a Groucho Marx-style disguise — black-rimmed glasses and a fake nose and mustache — in the back of his car.
“He thought it was hilarious,” Braden said, “because it’s the stupidest disguise you can come up with.”
But while Halladay didn’t enjoy the chaos, he did enjoy teaching. In 2011, Hudi played alongside Braden on a Florida team called the West Coast Warriors. Halladay, fresh off his second Cy Young Award, would stop by to help out.
One day, he approached Hudi during a bullpen session in Tarpon Springs. Halladay asked what pitches he threw. The 11-year-old’s answer was essentially “nothing.” He asked if he’d ever tried a cutter. Hudi shook his head.
Halladay grabbed a baseball and showed him a grip. Then he reached for a pen, and traced around Hudi’s hand, so the middle schooler could practice at home.
“He outlined where my fingers were,” Hudi said. “I thought that was so cool.”
Parents would ask Halladay if he’d be willing to coach, but he always demurred. The big leaguer wanted his son to carve out his own identity in the sport. Having a world-class athlete around would make that challenging.
But in 2014, he had a change of heart. Halladay had recently retired. Braden was only a year and a half removed from high school, and had experienced a few seasons on his own.
The son encouraged his father to join the coaching staff of his travel ball team, the Dunedin Panthers. Halladay stayed through 2015, serving as pitching coach and later head coach.
He did not take this role lightly. Once, a baserunner bowled over Dunedin’s catcher at home plate. The league’s rules stated this should be an automatic out, but the umpires didn’t call it.
Halladay was furious. He explained to the crew that they’d made a mistake. One umpire, who didn’t recognize the eight-time All-Star, told him that he didn’t “know the rules of baseball.”
This set off Halladay even more. He was ejected. Braden, who wasn’t standing far away, overheard a conversation between the officials not long after.
“He goes, ‘Hey, dude, you know you just ejected Roy Halladay, right?’” Braden recalled. “And the umpire goes, ‘Oh my God.’”
Halladay decided to have himself a day. He went to the concession stand and bought three cheeseburgers. He filled his big Yeti tumbler with Diet Coke, got in his truck, and pulled it behind the left field fence.
He sat there for the rest of the game, scrutinizing the umpire’s every call. If he missed one, Halladay would let him know it, loudly proclaiming that the official didn’t “know the rules of baseball.”
Braden enrolled at Calvary Christian in 2016. He spent his freshman year playing junior varsity, without his father, and was promoted to varsity as a sophomore.
Halladay joined head coach Greg Olsen’s staff that year. Hudi transferred in from East Lake High School in Clearwater not long after. He and Braden were close friends; Hudi would sleep over at the Halladays’ house fairly often.
To Hudi, the 6-foot-6 Halladay was not a star pitcher. He was an eccentric parent. One time, when the boys were older, Hudi made the mistake of drinking Halladay’s last Dr Pepper.
Halladay barged into the game room, where Hudi and Braden were watching TV.
“Who drank the last [expletive] Dr Pepper?” he asked.
Hudi, holding the can with trepidation, said he didn’t know.
The pitcher stormed out. He returned 30 minutes later with two six-packs.
“He’s like, ‘This six-pack is yours,’” Hudi recalled. “And then he holds up another case, and he’s like, ‘Don’t [expletive] touch this. This is mine.’”
Halladay brought the same attitude to the Warriors in 2017. Braden wasn’t used to seeing his father act this way on a baseball field.
“Whenever he was home, he was kind of a funny, not-take-things-too-serious kind of person,” he said. “It was more so that you’d notice at the field that he wasn’t doing that. And he actually was kind of a little bit scary.”
But at Calvary Christian, there was no pressure to uphold a persona.
“I think he just got to be himself,” Braden said.
A method to his madness
Olsen had been around a lot of coaches at this point, some of them former big leaguers. But he quickly learned that reaching the pinnacle of the sport didn’t necessarily translate to on-field instruction.
This was especially true when it came to resonating with kids. They could easily discern coaches who were sincere from those who were not. And if they deemed a coach insincere, it was over.
Halladay didn’t have this problem. He could explain grips and mechanical adjustments with ease (and without condescension).
He would go beyond telling a player what to do. He’d help them find their feel. That way, when the high schoolers were alone on the mound, they could throw a curveball or a splitter, or any other pitch, and make corrections in the moment.
The coach showed no favoritism, not even to his son. He studied like he was still in the big leagues, sitting on a bucket with his enormous iPad, scribbling notes during games and practices.
“It was like a 55-inch flat-screen TV,” Hudi said. “And he’s a big guy, so him holding that giant thing made it look even crazier. Nobody knew what he was writing down.”
He didn’t need to show them. Halladay routinely proved he’d done his homework. In 2017, he helped Hudi redesign his entire windup, from stepping sideways to stepping behind the rubber, with his hands overhead.
Halladay wanted the pitcher’s momentum going toward the plate; otherwise, his stride would be inconsistent.
“The wealth of knowledge was crazy,” Hudi said. “And it went so much further than pitch grips.”
Halladay helped his team with mental skills, too. Olsen would often see him talking to players between innings, to strategize for upcoming at-bats or guide them through a tough moment.
He’d tailor his mound visits to whatever was needed, no matter how unorthodox it looked.
Braden remembered one game when he was losing his command. Halladay walked out to the mound but didn’t say a word. He just stared.
After the inning was over, the pitcher approached his father.
“Hey man, what was that?” Braden said.
“Were you thinking about throwing strikes?” Halladay asked.
“No,” Braden said. “I was thinking about how weird that was.”
His father smiled.
“Exactly!” he said.
This was just one of many instances when Halladay was validated for his quirky ideas. He and Olsen would stand next to each other in the dugout, signaling pitches to Calvary’s catcher.
They usually agreed. But every once in a while, Halladay would propose something unusual. In the district semifinal, a formidable Tampa Catholic hitter took his final at-bat. He’d struck out twice earlier in the game on sliders.
Halladay wanted a fastball down the middle.
“He was like, ‘Look, we gotta go off script at some point,’” Olsen recalled. “And he was right. We threw a ball right down the middle, and the hitter froze. That was his genius of pitch calling.”
Two weeks later, in the regional final, Halladay called for a splitter in the ninth inning with a runner on first and a one-run lead.
There was one problem: The pitcher had never thrown a splitter in a game before.
“In that moment, I felt like this is either going to work, or our season could be over,” Olsen said. “Because the kid’s gonna hit it out. But he made the right call. We jammed him, he grounded out, and we won the game.”
Cairo, who was sidelined with a hand injury, had a front-row seat to all of this. Sometimes, the infielder would sit next to Halladay on the bench and go through pitch sequencing.
Other times, they’d just talk crap.
“I remember this one pitcher was talking a lot after we scored like six runs on him,” Cairo said. “Roy told him to go sit in his truck or something like that. That was fun.”
Calvary Christian didn’t lose a game that year. The Warriors were perfect in the regular season — despite enduring injuries to multiple players — and made it to the state championship in Fort Myers in late May.
By now, everyone knew of Halladay’s idiosyncrasies. So no one was surprised when he was caught flying a drone over Pensacola Catholic’s practice.
The opposing coaches saw a metal device whizzing through the air. They told a security guard, who spotted Halladay in the dugout with a remote control and a grin.
The security guard was not as amused. Had anyone else pulled this stunt, they would’ve been kicked out of the game. But Halladay knew the tournament officials wouldn’t do that.
He got a slap on the wrist.
“The official was like, ‘Hey, dude, like, you can’t spy on the other team with aerial equipment,’” Braden said. “And he was like, ‘Ahhhh … sorry, sorry.’”
‘I really felt him there’
The drone surveillance didn’t end up being necessary. Calvary Christian won the Class 4A state baseball title handily. By the sixth inning, they’d amassed an 11-1 lead over Pensacola Catholic. The game ended by mercy rule.
The high schoolers sprinted from the dugout, jumping into a dogpile. Halladay flitted around the group, giving bear hugs big enough to lift players off the ground.
He and assistant coach Mike White hoisted Olsen on their shoulders, as he carried a wooden trophy. The former Phillie beamed from ear to ear. This wasn’t a World Series. But it was sweet all the same.
Halladay couldn’t wait to do it again next season, which is why he arrived to an exhibition game in full baseball garb in early November. But that would be the last time he’d see his team.
Braden described the days after his father’s death as a blur. Teammates and coaches came by the house to express condolences. Cairo and Hudi barely left his side.
On Nov. 8, Olsen gave the younger Halladay a call. Calvary Christian had another exhibition game scheduled for Nov. 9, against East Lake.
Braden was supposed to start, but Olsen said they could cancel it altogether if he wanted. He told his coach he would think about it.
Less than 24 hours later, Braden was in his car, driving to the ballpark. As he warmed up in the bullpen, he heard a loud noise.
The high schooler looked toward the sky to find a small airplane flying overhead.
“It looked exactly like my dad’s,” he said. “That brought me closer to him in that moment.”
At 7 p.m., Braden stepped onto the mound, with his father’s Calvary jersey hanging in the dugout. A typical November game would draw about 30 to 40 people; on this night, there were four to five hundred.
Braden insisted that he’d take it one inning at a time, but once he started, he couldn’t stop. Four frames later — a long outing by fall ball standards — he’d allowed one hit and no runs.
Braden told Olsen he was done. He walked off the mound, grabbed his father’s jersey, and began to cry.
“Obviously when he passed away, my thought was, ‘I lost my father,’” he said. “But that was my first moment of … he’s still with me. I still have him. I really felt him there.”
The players circled around the mound and said a prayer. Someone took a photo and sent it to Braden. Through the darkness, a ray of light shined down on his head.
A different side of Halladay
On Nov. 14, 2017, the Phillies held a celebration of life at their spring training complex. It was open to the public; thousands of people attended.
After the ceremony, Halladay’s friends and family moved to the batting cages beneath the stadium. Standing on bright green turf, with the nets pulled back, they grieved.
This was the first time many of his players had met his Phillies and Blue Jays teammates. And as the high schoolers traded stories with Chase Utley and Ryan Howard and Cliff Lee, it dawned on them that they’d seen a completely different person.
The former big leaguers painted a picture of a cutthroat competitor; a titan of the sport whose intensity seeped out. To the boys of Calvary Christian, he just was a goofy dad.
This is how they will remember him. They’ll never forget the perfect game, or the postseason no-hitter, or the countless shutouts. But for those 17 high schoolers, who are now 17 men, the coach they knew meant so much more.
