"You don't understand. This guy gets up 5:30, 6 o'clock every morning," Curran says. "By the time I talk to him—and we talk every day between 7 and 7:30—I can tell by the sound of his voice whether our clients had a good or bad night the night before. He knows how everybody did; if someone's minutes are down, we know he's either injured or hasn't done what he should've been doing. And by the end of the conversation we have a list of seven or eight items for that day that we're going to address. Involved? He still lives and breathes it."
Endorsement contracts and public relations work had lifted Orr out of the financial ashes left by Eagleson, and in 1996 Orr bought into the Boston agency created by Bob Woolf. Now agenting gave him a chance to attack business as relentlessly as he did the game. "Dozens of calls every day—to players, to scouts, to skill coaches: How's our guy doing?" says Jay Fee, who worked at the agency before going out on his own in 2002.
Orr also drew a clear line: His agency would not handle—as Eagleson had—player finances. "Being victimized by a bad agent, I think Bobby wanted to run a business that would never do that to anybody," Fee says.
Still, Orr leaves much of the on-the-ground detail to his partners. The Flyers' Jeff Carter—handled primarily by the Philadelphia-based Curran—emerged as a breakout star for the firm this season, and he has scarcely any relationship with Orr. Meanwhile, Orr's Boston-based partner, Paul Krepelka, is the agent of record in DiPietro's case; he represented the Islanders goalie up to and including the moment DiPietro signed a record 15-year, $67.5 million contract in 2006. The relationship frayed soon after and DiPietro fired the firm, refusing to pay its percentage because he had never signed a standard player agent contract. Last summer, Orr filed a grievance with the NHL Players' Association, but DiPietro—who declined to speak to SI—says he owes nothing. Krepelka agrees that DiPietro didn't sign a contract with the Orr Group, but says he negotiated the pact and should be paid. The grievance is expected to be heard this spring and "could segue into a lawsuit," Krepelka says.
Orr's role, though, was never about pen and paper. Then and now, he has traveled widely to take in college and pro games, bundled golf rounds with contacts in coaching and broadcasting, used his stature to gain an entrée denied rival agents. He often showed up unannounced at the Maple Leafs' offices when Pat Quinn, his old sparring partner, was coach and general manager from 1998 to 2006. Quinn usually didn't deal with player reps, but he always welcomed Orr. Eventually talk would turn to a client like defenseman Tomas Kaberle, and Quinn says, Orr would "get to where he wanted to go. And it was always about the kid, about his best interest." When, during Kaberle's 2001 holdout, hockey analyst Gord Miller of The Sports Network in Canada took an on-air shot at Kaberle's defense, Orr got in Miller's face, stats at the ready, snapping, "You'd better rethink that!"
Orr's loyalty to the faithful is just as fierce. If he has refused to donate signed pictures or gear to a desperate fan, or refused a charity golf tournament or hospital visit, no one has heard of it. In 2006 a story ran in The Boston Globe about a high school hockey player, Bill Langan, who played in a regional title game on the day of his mother's wake; the kid mentioned that his mother used to watch Orr play. Orr called, asked if he could help. Langan asked him to come to a team dinner. Orr made no promises. But he showed up without warning and stayed an hour.
As for the big, bad—and now old—Bruins, Orr is, Sinden says, "still the Godfather." When the flamboyant and reckless Sanderson showed up in Chicago in the winter of '78 stoned and unable even to hold a cup of coffee steady, Orr personally checked him into a hospital and was there when Sanderson woke up with three doctors staring at him. "Who's going to tell him?" one said.
"I'll tell him," Orr said and then leveled with Sanderson: "You're a full-blown alcoholic and a drug addict. It's over. You've got to go to rehab." Orr paid for that first stint. When Sanderson relapsed, he says, Orr paid to send him back. And then again. "He never left me," Sanderson says.
When Sanderson finally cleaned up, and began a new life as a financial adviser for athletes in the 1990s, Orr invested with him, gave Sanderson the chance to work with Orr's clients too.
Orr also paid for rehab stints for former Bruins trainer John (Frosty) Forristall, his roommate during his first years with the Bruins and an irreverent bon vivant whose alcohol problems led Esposito, then the general manager of the Tampa Bay Lightning, to let him go in 1994. Forristall returned to Boston jobless, and soon after he was told he had brain cancer. Bobby and Peggy took Forristall into their home for a year until he died in '95 at 51.