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Michael Bonanno
Show Me The Money


He is an anomaly in the land of sleaze—a straight-shooting, puppy-dog-loyal Jerry Maguire, minus the taste for alcohol. “I have a drink maybe three times a year, and even then I’ll nurse that beer for an hour,” says Michael Bonanno, a handsome, olive-skinned 23-year-old who has two cell phones to keep his clients in check and probably two sets of adrenal glands to supply his boundless energy. Sporting a neatly trimmed week-old beard, Bonanno is charismatic and engaging as he spills the truth about the world of sports agents and their much-sought-after clients over lunch in Waterdown, a short drive from his parents’ farm in Kilbride.

Bonanno still lives at home, but, as with his tender age, that’s irrelevant. A co-founder and vice-president of athlete representation of Oakville-based Oak Sports Management, which opened for business a year ago, Bonanno was the youngest agent at the 2009 Major League Baseball Winter Meetings in Indianapolis, although he was sort of there by default. His first dream was to play Major League ball. Light years ahead of his teammates by the age of seven, the Oakville
native eventually garnered a two-year ride at Brevard College in Florida, where he competed with and against blue-chip stock, with 22 players within his conference being drafted into the Majors during his two years there. But when Bonanno came to accept that his number wasn’t going to be called, he looked to his roots in making the jump to professional ball, signing with Fortitudo of Bologna, Italy.

“My parents weren’t the biggest fans of the decision. They support me no matter what, but they wanted me to stay in school,” he says. “But I wanted to chase the dream. It seemed like a perfect fit—going to the country where my parents were born and getting paid to play baseball. It doesn’t get much better than that.”

Actually, it got worse. “Italy just wasn’t a good fit,” admits Bonanno, who was fleeced by local merchants (who took advantage of his lack of Italian) and later sidelined by a torn UCL in his right elbow (the rehab of which would likely have seen him lose his starting shortstop position on Fortitudo). “It was a hard decision, because I knew if I went home, my baseball career would probably be over. But I felt it was time to man-up and start up a different part of my life. My dream of playing in the Big League made it past me, but it happens. Only one in every 1,003 high school seniors playing ball get to play just a single day in the Majors.

“When I came home, I didn’t know what I was going to do,” Bonanno recalls. “I worked at Sport Chek and other part-time jobs, and then Peter Lambert, a family friend since I was about four years old, came over to my parents’ place one day for lunch and asked what I was planning to do now. I said ‘Be a sports agent,’ which was another dream of mine since I was a kid. I loved Jerry Maguire! I’d spoken with (NHL agent) Donny Meehan and baseball agents like Joe Bick (of Pro Star Management). So early on I contacted a friend and asked, ‘Who was your agent when you played?’ And he said, ‘Joe Bick—here’s his email address. Feel free to ask him any questions.’ So I wrote Joe and I told him I’m just starting out and asked if he might be able to answer some basic questions—because I didn’t know anything about the sports agency business except contract negotiations and what I’d seen in the movies. He was very helpful with the ins and outs of the business.

“Peter decided to have a meeting with me and Don Webster, who’s been the head legal counsel of one of the world’s top consulting firms. They were going to have to sink a lot of money into this, so they wanted to know about me and asked, ‘Why do you think this can be successful?’ And I said, ‘I know the most talented baseball players around. I’ve played with them, against them. I personally know guys in the Major League. I just need the backing and the legal part to be able to do this.’

“Peter has the finance background,” Bonanno notes. “He helped run a successful firm for a while, so his role is taking care of our players’ finances and making sure they they’re in good financial shape when their career is over. Don’s role is the legal side of it, with contract negotiations and arbitration. And I’m essentially the face of the company.

“We’re big on the team approach,” Bonanno says of the two other co-founders and the seven-man firm—not including his sister Tasha, who takes care of the administration work and acts as a background scout—when both of his cell phones go off almost simultaneously.
“It never stops,” he smiles, muffling both ringers. “My ex-girlfriend and I broke up a year and a half ago, and I haven’t been on a date since, and I haven’t been out on a weekend since New Year’s. I don’t get much sleep. But this is what I want to do. I had a fallback playing baseball. But I have no fallback from being an agent. So it’s ‘Don’t fail—do whatever it takes!’ I’ve read the MLB Players’ Collective Bargaining Agreement like three times—all 229 pages—and I don’t like to read!

“But now that our client list has grown, my job has gotten easier, because you’re dealing with higher-end players who are lower maintenance,” Bonanno explains. “We used to have a few prima donnas—players who are mainly concerned with free gear. They think I’m Dick’s Sporting Goods. On the flip side is someone like Brad McElroy or Randy Schwartz, a free agent signed by the Toronto Blue Jays—our first client. Both are Canadians and the nicest people you will ever meet. I send Randy batting gloves and he calls me like three times to say thanks.”

Schwartz was the guinea pig. “I said to him, ‘I know you don’t have an agent, but could you do me a favour and let me represent you and we’ll see how it goes?’” Bonanno relates. “At that point in his career, he was still a few years from needing an agent, but it would be a win-win for both of us.”

Bonanno’s inside knowledge has quickly positioned him as a serious prospect in his profession, even if he looks a tad baby-faced for the job. “At the Winter Meetings, people thought I was at the job fair that takes place every day that week. They kept wondering, ‘Why is the kid at the job fair coming to all these prestigious dinners—Scout of the Year, Executive of the Year?’ That’s a part that I don’t like—don’t judge me by my age; judge me by what I do.”

Many already have. Former Major League Baseball scout Jim Devine believes Bonanno is destined for stardom. “Michael is a young, brilliant baseball mind that will be in this game for a long time. He has all the qualities to succeed,” says Devine. “His knowledge of the game and strong character is one of the reasons he is one of the youngest sports representatives in MLB history.”

Testimonials like that seem to be flowing from Bonanno’s wake. “He works overtime to take care of my personal interests,” says client and Arizona Diamondbacks prospect Justin Mace. “He will go to bat for his clients and treats you more like a person than a player.”

“Michael has everything that it takes to be one of the top agents in this industry,” adds an American League executive and former member of the New York Yankees organization under condition of anonymity. “He is smart and not afraid of any challenges. Mix that in with his business sense and negotiation tactics (and) he is the definition of a player agent.”

Not that there hasn’t been a learning curve. When you swim with sharks, you occasionally get your tail bitten. “At the Winter Meetings I had a local befriend me, tell me about a player he has and invite me into a meeting where we were trying to sign this kid. The whole time he was working for another agency and wanted to learn our entire pitch. It was one of those times where I thought, ‘Sonofabitch—you got me.’”

It’s a cutthroat world, Bonanno concedes, relating a story of a National League executive who expects to be released, and the agency that has secretly hired him to try to push every player on that team toward their agency. Oak Sports is trying to distinguish themselves from that pack. They have a network of training facilities, coaches, physicians and sports psychologists to appeal to their 22-player contingent (a number bolstered by seven with the January acquisition of Palmetto Sports Council, a South Carolina agency operated by MLB agent Jeff Cordova). But they also tend to the subtle world of image-building. “Dealing with media and fans is extremely important,” Bonanno stresses. “I tell our guys, ‘I don’t care what you do with your personal lives, but when you show up at the park, you have an obligation. Sign some autographs—you can make a kid’s day.’ It can go a long way within an organization, especially when you’re on your way up. The team can look at a player and see that he has a following; that he has a Facebook fan group. Those guys sell tickets. It takes 10 minutes a day to walk that autograph line.”

Bonanno and company also play their part. “We do some unique stuff. Every Mother’s Day we send our players a pink bat—cancer research—they can use and then give away to their moms or someone in the stands after the game.”

Players are beginning to appreciate Oak Sports’ personal touch. “We’ve helped plan a wedding,” Bonanno notes. “If they move to a cold climate, we’ll send them some Under Armour stuff to help keep them warm. We care about our players. But at the end of the day it’s a business, and our job is to get as much money as we can for them come contract time.”

That’s what truly ignites Bonanno’s fire. When Palmetto merged with Oak Sports, Bonanno secured a deal a month later with Easton Baseball for Ben Swaggerty, a AA Pitcher of the Year for the Kansas City Royals who’d been three years without an endorsement contract.
But the standard agency cut of four to six percent of player salaries is for Big League talent only. “According to the Collective Bargaining Agreement, you can’t charge a minor league player a dime off their base annual salary. So the only time I can make money is through cash endorsement deals, or when they get drafted,” Bonanno explains. “The saying in the agency business is that you get rich off the draft.”

But it had better be a good draft pick, since four to six percent of a six-figure salary doesn’t go very far, particularly when you’re already shelling out $1,500 to $2,000 per minor league client in equipment and dinners to visit them. But there’s a price to play at this level.

“The company funds basically anything I ask for. If I say I need $5,000 for spring training, it’s there,” says Bonanno. “But I don’t take advantage of it. And at the same time, I’ve put in a decent chunk of change myself—every dime I have, I try to contribute to the company. I believe in what we’re doing, and I know our clients do too, otherwise they wouldn’t be with us.
“It’s an investment for us,” Bonanno says, crossing his fingers that the prime prospects they now cling to are still their clients when seven- and eight-figure contracts are signed down the road.

There are no assurances. Oak Sports allows its players to walk if they choose. But Bonanno believes they’re building bonds that will survive both the test of time and the temptations of greed. “Most agents are like protective boyfriends,” he explains. “They sit and watch their players at spring training and make sure that nobody ever talks to their guy. I’m like, ‘Talk to my guy!’ If you can service him better than me, go for it, because there’s no way you can.’”

Bonanno walks and talks with the swagger of someone who’s been in those players’ shoes, but also of a man who has probably gleaned more information off of young pros and veteran agents than any man alive over the past 12 months—research that has helped him determine what other agents do that their players love and hate. It also helps that Bonanno was weaned among professional athletes thanks to his father Augie’s car dealership and sports memorabilia connections.

“I think that affected me a lot,” Michael says. “Being able to sit in a limousine with Mats Sundin (my dad picked him up from the airport after he was traded from Quebec to Toronto for an autograph signing at President Sports in Oakville), or having Wendel Clark over to my parents’ house in Oakville for dinner. He’d bought a car off my pops. He wore a cowboy hat, denim and cowboy boots, and I would have told you he was 7-foot-5 and invincible—my idol coming over to my house for pasta dinner. And being able to walk into the Blue Jays dressing room and interact with Candy Maldonado and Juan Guzman, or being able to walk into the Maple Leafs dressing room because people know who I am. It taught me to adapt to the environment I’m in now. It showed me that these icons were actually real people. Like you and me, some have good days and some have bad days. So I’m not intimidated being around famous players and management. I’m comfortable there.”

It makes for an effective combination—confidence bred from personal experience among the elite, coupled with a business savvy that suggests Bonanno is as quick on his feet at the negotiating table as he was at middle infield. Together, they’re opening the doors of a previously closed shop.

“Baseball is like a fraternity,” Bonanno says. “It can seem impossible to get into the fraternity, but once you’re in, you’re in for life. For me, the door kept getting shut. At the beginning, I wouldn’t get emails back from scouts. I sent out 250 emails and letters to scouts asking for their contact information to ask questions, and nobody would reply. Now I look at my in-box and they’re contacting me.”

So are his players. “I’ve gotten drunk-dialled, asking me if he should bring home a blonde or a brunette,” Bonanno laughs. “I thought it was an emergency—that he was in the hospital, in jail, hurt.”

So did Bonanno say the blonde or the brunette? “I said, ‘You wake me up for this? Bring home both!’ And I hung up.
“My clients know that my phone is available night or day, no matter what the issue is. They’re the only ones who have my second cell number. And they know I keep the personal stuff between us. I’ve had guys call me crying after a break-up. I’ve called the parents of players who were having surgery—‘Can you tell my mom that I’m OK.’ I love knowing that they know they can trust me—that I can help make an impression on their lives.

“When my player retires, I want to be the guy beside him, just out of the picture, like in Jerry Maguire—‘That’s my arm around the player in the picture.’ I want my hand in the picture—not my face—
because it means my players are still there and succeeding, but I’m still there and they care about me.”

Bonanno’s willing to go a long way to ensure that his clients are looked after, but there is a nebulous, ethical line.
“They’ve told me that in this business you have to have the heart to be able to screw your best friend if you’re going to be great,” he says. “I don’t have that. But I’ll settle for doing it my way and just being really, really good.”