The improbable rise of Alex Anthopoulos

Aroldis Chapman, a left-handed pitcher for the New York Yankees, is owner of the fastest fastball ever thrown: 105.1 miles per hour. They call him “The Cuban Missile,” which is quite a compliment. To missiles.

Back in December 2009—nearly a year before he uncorked that record-setting pitch—Chapman was a highly coveted but somewhat mysterious free agent, a skinny, 22-year-old defector whose magical arm was more word-of-mouth legend than radar-gun fact. Few scouts had actually seen him with their own eyes, and even as major league teams lined up to bid for his services, baseball executives were scrambling for scraps of intelligence on the game’s latest phenom. Smack in the middle of that hunt was an equally unknown rookie: Alex Anthopoulos, who, at the tender age of 32, had just been named general manager of the Toronto Blue Jays.

“It was like going into an exam,” he says of the Chapman pursuit. “You had every intention of trying to do well, but you opened up the book the night before and tried to cram.” And when Anthopoulos says “the night before,” he means the night before his wedding—and the day of. “I don’t want to say too much,” he smiles. “My wife is going to read this and really want to kill me.”

The church was booked for Jan. 2, 2010, a Saturday. On the Wednesday, Anthopoulos broke the news to Cristina, his very patient fiancée: he had to fly to Florida to watch Chapman throw a private bullpen session.

“What do you mean?” she said. “We’re getting married in a couple of days.”

“I gotta go,” he told her. “It’s a big guy, a lot of money.”

On Thursday morning, New Year’s Eve, Anthopoulos and others from the Blue Jays front office huddled around a mound, watching Chapman hurl his heaters. The pop of the catcher’s mitt was certainly impressive, but the rumoured price tag (at least US$20 million) was a lot of cash, especially for a man throwing practice pitches. “I was agonizing about it,” says Anthopoulos, now 33. “It was a tough decision, and to spend that kind of money you should have a comfort level.”

The next day, Jan. 1, the G.M. was back in Toronto, celebrating with family and friends at his rehearsal party. When the festivities wrapped up, Anthopoulos returned to his downtown condo—where he promptly convened a midnight conference call to talk some more about the Cuban. “It’s something I still laugh about today,” says Perry Minasian, one of the Jays officials who was on the line (and also in the wedding party). “We were on the phone until maybe 2:30 in the morning.”

At 7 a.m. sharp, when George and Bill Anthopoulos came by to collect their kid brother for his big day, Alex was running a bit behind. “He wasn’t even dressed,” says Bill, the best man. “He was on his BlackBerry. I was freaking out!”

After endless hours of conversation and contemplation, Anthopoulos had decided that Chapman’s raw talent was worth the risk. He informed the pitcher’s agent that he was heading to Hawaii for his honeymoon, but promised to email a dollar figure before he left. So as his ushers headed to the ceremony in the back of a stretch limo, the groom was clicking away beside them, ironing out the final details of his offer. “I’ve been in a lot of other wedding parties where people are knocking down shots,” Minasian says. “We were talking about Chapman. The guy is relentless. He really is.”

Finally, in the basement of the church, Anthopoulos switched off the phone. His offer was sent, just in time for the bride. “It was classic Alex,” says Michael Yermus, another groomsman and long-time friend. “I kept saying: ‘Listen, you know you need to turn that off as soon as we go upstairs, right?'”

For the record, Anthopoulos handed the phone to his eldest brother and swears he didn’t check his email again until the following day. “There is no question, leading up to going to the church, I was on my BlackBerry,” he confesses. “I’m not proud of that at all, but I’m not going to lie. I needed to put our offer together, and I’m very meticulous.”

Meticulous doesn’t even begin to describe him. It’s like calling Aroldis Chapman a knuckleballer.

It’s been 18 months since Anthopoulos was hand-picked, seemingly out of nowhere, to breathe life back into the once-mighty Toronto Blue Jays. Every decision, from draft picks to trades to multi-million-dollar contracts, is ultimately his call. But as the faithful gear up for his second full season in command, the question lingers: who the heck is this guy? What makes a guitar-playing Montrealer who can barely swing a bat—and whose birth certificate was issued in 1977—the right man to lead the Jays back to playoff glory?

Ask anyone who knows Anthopoulos, and the answer is always the same. “He is overdosed on passion,” says Dana Brown, a former Expos executive who gave Alex his first scouting job. “He has worked so hard and put in so many hours that he got his degree in baseball a little faster than most. In baseball years, he’s probably 50, not 33.”

Long before he made headlines for trading away Roy Halladay and Vernon Wells, Anthopoulos was the guy opening fan mail and fetching sandwiches and peppering pro scouts with countless questions, soaking in everything he could. When he finally did land a paying job, he worked such long hours that a security guard accidentally locked him in the office. Fans pining for the days of Robbie Alomar and Rance Mulliniks can at least be sure of one thing: if the players are one-tenth as energetic as Anthopoulos (and run half as fast as he talks) the Yankees and Red Sox are in for a fight.

“I have been around a lot of great baseball minds, but he has a special ability to look at a player from all different angles,” Minasian says. “His hunger for information, and his ability to process that information, is different from anybody else’s. It’s amazing the way he’s wired and the energy he has.”

Even on his honeymoon, as the Chapman saga unfolded, Anthopoulos found the time to squeeze in some negotiations. “When we were lying down on the beach, as soon as I closed my eyes, he was on his BlackBerry,” Cristina laughs. “When he really wants something, he’ll go after it. He’s chased his dreams, and not a lot of people can say that.”

Those dreams were born in the front row of Olympic Stadium, directly overtop the Montreal Expos’ first-base dugout. Yermus’s dad had a set of season tickets, and during their high school years Michael and Alex took in dozens of ball games from the best seats in the yard. “I got the bug,” Anthopoulos says. “If I find something I really have a passion for, I don’t want to say I get obsessive about it, but I immerse myself in it.”

John Anthopoulos, his father, was a Greek immigrant who came to Canada and worked his way through McGill University, earning an engineering degree and opening his own heating and ventilation company. Whenever he walked into a building, he would instinctively stare up at the ceiling, inspecting the equipment. John’s youngest son inherited his curiosity—and his work ethic. “Even as a kid, he was tenacious,” brother Bill says. “My dad used to always say: ‘When Alex wants something, boy, you better watch out.'”

Especially if you’re the one on the receiving end of his questions. Whether it was poring over box scores or learning to play the bass, Anthopoulos was inquisitive to the point of exhaustion. “He wants to know everything,” Yermus says. “We’d go to a movie, and he’d ask the guy selling the tickets about the movie. The person ripping the ticket, he’d ask him. The guy at the concession, he’d ask him. The only thing that’s really changed is that back then, he’d already bought the ticket. Now he asks the questions before he buys.”

Anthopoulos studied economics at McMaster University and spent the summers working at his dad’s shop, welding coils and driving a forklift. His plan was to finish school and make the family business a career, with his father guiding him along. But on May 15, 1998, everything changed. “It’s crazy to say, but I wouldn’t have gone after all this if my father hadn’t passed away,” Anthopoulos says now, 13 years after the heart attack. “I would take my dad back in a minute, but it was a life-changing event, and I’m a big believer that everything happens for a reason.”

Suddenly, Alex and his brothers were in charge. As always, he immersed himself in the minutiae and learned everything he could as fast as he could. But after two years of gruelling days and sleepless nights, he accepted the truth: as much as he adored his dad, he didn’t share his love for ventilation. The brothers sold the company, and at age 23, Anthopoulos started searching for an opening in baseball.

Over and over, he phoned and emailed every professional team, telling anyone who listened that he would do any job, do it anywhere, and do it for nothing. Anthopoulos finally caught his first lucky break in March 2000, when he called the spring training of?ce of the Expos’ GM—and the GM answered. “A lot of people think it’s unusual for me to answer my own phone, but I did it often,” Jim Beattie says now. “In Montreal, not too many people called me.”

Beattie kept the kid’s name on file, and later that season, Anthopoulos received a return phone call. The Expos needed a volunteer to come to the clubhouse during weekend home games and sort the players’ fan mail. “I said: ‘Yeah, great, I’d love to do it.’ ”

There was only one problem: while waiting for his baseball fantasy to come true, Anthopoulos had hired a headhunter to help him find a job in the real world. And just as the Expos called, a Bay Street investment firm was looking to hire him. “So now I have both job offers,” he says. “One is actually paying, a career, upside, all that stuff. The other is non-paying, weekend home dates.”

In his mind, the choice was obvious. “I called up the headhunter and said: ‘Look, I’m sorry, but I’ve got to turn this down.’ ”

Michael Yermus still shakes his head at that one. “I really admire him,” he says. “I went to law school, and in retrospect I’d much rather have his job than my job because it’s a lot more interesting. But I never would have had the courage to do what he did.”

Anthopoulos worked as a bank teller during the week, but counted down the minutes until the team was in town for a Saturday-Sunday series. He would go in early, sort the mail, and then use his clubhouse pass to watch the game from the scout seats behind home plate. “He asked a million questions, but he was very respectful,” says Mike Toomey, a long-time scout who befriended Anthopoulos that season. “There were a couple older scouts there, and they said: ‘How come you spend so much time with that kid? He’s a nobody.’ I’ll never forget what I said: ‘You know what? He’s a good kid, he’s very energetic, he loves the game—and he might be your boss one day.’ ”

As the season wound down, Anthopoulos talked his way into his next “job”: a U.S. baseball school connected to the Expos. Again, he chuckles at the timing. “I said: ‘Absolutely, I’m all over it.’ In the meantime, the bank comes to me and says they want to promote me to commercial banking. I just said: ‘You know what? I’ve got this opportunity to go down to Florida and work for free…’ ”

He stayed for almost two years. Most of his tasks were menial (driving kids to the airport, picking up lunch) but he got to spend hours a day on the diamond. “He would just pick my brain all day,” remembers Randy Kierce, who ran the academy. “Alex was not the most athletic person around. We used to laugh about how part of scouting is projecting body types of players, and we used to say: ‘You know Alex, I don’t know if your body type will ever play out in pro ball—unless it’s as a GM.’ But we also told him that he will be a GM one day because he has the makeup upstairs.” (Nearly a decade later, Anthopoulos still remembers Kierce’s cellphone number because he dialled it so many times).

By spring training of 2002, the soon-to-be-extinct Expos were under the control of Major League Baseball, and Anthopoulos, now 25, was once again a clubhouse volunteer. “It was another non-paying internship,” he says. “I was thinking: ‘This is it. I’m on my last stretch here. If this doesn’t happen, I have to grow up and get a job.’ ”

It was Dana Brown, the team’s new scouting director, who finally went to bat for him. He needed a scouting coordinator (an administrator whose primary job is to organize the annual draft) and he lobbied the new GM to hire Anthopoulos. “He wore a lot of hats almost from the beginning, and his career absolutely took off,” Brown recalls. “He asked so many questions, but it never got old. He would call me at one in the morning, and my wife would look at me and say: ‘Who was that?’ I’d say: ‘It’s my assistant in the office. He’s watching scouting films and wants me to talk about players.’ My wife would say: ‘We’ve gotta find him a life.’ ”

Alex, though, had already found it. He had squeezed and clawed his way into the baseball universe, and over the next six years he would scout Canada for the Expos, make the agonizing decision to jump to the Blue Jays, and impress absolutely everyone who crossed his path. “He is always looking for an edge, and he asks a million questions—a million,” says J.P. Ricciardi, the former Blue Jays GM “You could tell he was aggressive, and wanted to make himself better.”

In 2005, Ricciardi had seen enough. “I called him into my office and said: ‘Alex, how long do you think it will take you to learn the responsibilities of an assistant GM?’ He told me: ‘I don’t know, but I guarantee I’ll work as hard as I can.’ ”

At the Blue Jays’ spring training diamond in Dunedin, Fla., Anthopoulos occupies a second-floor office just beyond the right-field fence. Steps from his desk is a party-sized patio with a few pieces of outdoor furniture: brown wicker with green cushions. If life were fair, every baseball fan would have the chance to taste such a view, even for one pitch.

But you won’t find the GM reclining on his balcony. Even if Anthopoulos wasn’t so ridiculously busy, he’s not the type to relish the spoils of his position. “This is going to sound arrogant, but I will never, ever, ever, ever get a big head or think I have it made or think I was born for this job,” he says, sitting in the of?ce as his team takes morning batting practice. “This could be gone tomorrow, and that’s not eyewash or false humility. I’m a sports fan. You can be king one day, and goat the next.”

He saw it first-hand with Ricciardi. At the end of the 2009 season, Anthopoulos watched his mentor and dear friend get shipped out the door—only to be told that the job was now his. “It wasn’t a good day,” he says. “I hate to put it that way, but it wasn’t.”

True to form, though, Anthopoulos dived straight in. The team was in Baltimore that weekend, playing its final series of the year, but the new boss spent most of his time at the hotel, brainstorming his next moves. In the coming weeks, he would double the team’s scouting department, deal Roy Halladay to the Philadelphia Phillies, and, with the wedding looming, set his sights on Aroldis Chapman. This off-season, he made an even bigger splash: dumping Vernon Wells and his $86-million contract on the Anaheim Angels, a move that only bolstered his growing reputation among fellow general managers.

All the while, his master plan remains the same: to stock the Blue Jays’ farm system with young, high-ceiling, high-performing athletes who will one day round out a championship roster—or be dangled as trade bait for players who can. The goal is not to compete for a World Series in 2012 or 2013, but every year. “I’m not a big believer in: let’s go spend a bunch of money trying to get a short-term fix, hope everything clicks, and hope everything else follows suit,” he says. “We need to methodically build it up together.”

And it’s hard to find anyone more methodical. If Anthopoulos dreams of an idea, he sends himself a text message in the middle of the night. He asks everyone for input, including the clubhouse cook. (“Sometimes players will let their guards down around certain people because they think: ‘Ah, it’s just the cook.’ “) If he’s scouting a team on a cloudy afternoon, he looks to see if any of the players have sunglasses on their caps—a potential preoccupation with “flash and style.” He recently went shopping for a second family car, and after months of research (fuel economy, insurance costs, safety features) he settled on a duplicate of the Honda CRV he already had. His is black; Cristina’s is white.

On the wall of that office in Dunedin is a nameplate of every single player in Major League Baseball, ranked on a scale of two to eight (fringe to Hall of Fame) and colour-coded according to where they were drafted: high school, junior college, four-year college, or international. Of the game’s top centre fielders, for example, the wall reveals that most were signed straight out of Grade 12. “Is this the Bible? No,” Anthopoulos says. “But maybe we need to take some chances on some high school centre fielders to get where we want to go.”

It is that attention to detail—and the ferocious pursuit of those details—that has the Blue Jays brass optimistic for the future. “With him, there will be no stone unturned,” says Jon Lalonde, a team scout who first met Anthopoulos in 2001. “He is as fundamental and processed with his decision-making as anybody. I wouldn’t doubt for a second that he would ask the janitor for advice.”

Blue Jays president and CEO Paul Beeston, the man who chose Anthopoulos to be GM, goes one step further. “There are certain prodigies that come along, and he was a prodigy,” he says. “The only problem is you can’t have a short conversation. I’ve told him I’m going to get an egg timer.”

These days, Anthopoulos has yet another responsibility occupying his time: a new baby daughter. Julia was born on Sept. 24—the same day, funny enough, that Chapman threw his record-setting fastball.

Not surprisingly, Alex the father is no different from Alex the general manager. “I don’t want to say he’s paranoid, but he is so worried about everything with the baby,” Cristina says with a smile. “He’ll Google something, he’ll call the doctor, he’ll ask the trainer, he’ll ask his brothers and his cousins. He’ll call everyone we know and ask: ‘Is this normal? Is that normal?’ That’s just who he is.”

Chapman, by the way, chose the Reds over the Blue Jays because they offered him the most money (six years, US$30.25 million). As a policy, Anthopoulos doesn’t reveal dollar figures unless a deal is signed, but it’s obvious that the Jays were not willing to venture quite that high. “It’s not that you’re always going to be comfortable with every decision you make, but I don’t want to be uncomfortable because I’m lacking information,” Anthopoulos says. “That’s the difference. I wasn’t as armed as I needed to be.”

Don’t expect that to happen again. Just ask his groomsmen.