He’s Attorney James Sokolove

And those cheesy ads of his? They've done more than make him a pariah and a punch line. They've also created an under-the-radar empire that's about to reinvent the business of ambulance chasing yet again.

Sokolove has since also discovered that his most successful ads are the most formulaic. Unadorned with fancy graphics, they speak to very specific audiences (patients who once took a drug the FDA has pulled off the market is a big one). These ads always display his toll-free phone number and website address for the duration of the segment, to allow plenty of time to write it down. Sokolove—wearing his lawyerly suit—speaks directly to the camera, in a style he describes as “serious but not stern.” He knows from his research that most people think hiring a lawyer means paying up front, so he always explains that it costs nothing to talk to him. He never brings up any of his affiliates, because that only confuses viewers. And he always, always mentions the potential rewards. The message behind his ads, he says, is simple: Injured? Free money.

Sokolove is equally direct when people attack that approach. Even in the halls of academia he’s unapologetic. During a recent talk at Suffolk Law, a student spoke up to challenge Sokolove’s explanation that it wouldn’t be cost-effective for him to pursue a malpractice suit he couldn’t win or settle for at least a million dollars. “I’m proud of my values, I give a lot to charity,” Sokolove said, “but I’m not in the religion business.”

“You just called helping your fellow man ‘the religion business,'” the student pointed out.

“Do you see a problem with that?” Sokolove shot back. “You can’t help anybody if you go bankrupt.”

Sokolove’s own family has gotten used to people thinking of him as a heartless ambulance chaser. “We all understand why he’s made fun of,” says his wife, Stephanie, who operates the popular eatery Stephanie’s on Newbury. “What you don’t get from TV is how gentle Jim is. On a personal level he would just as soon get along and work things out. The biggest misconception about Jim is that he’s a scumbag.”

The couple first met in 1996, at the wedding of a mutual friend. Stephanie remembers thinking, “Oh, here’s that guy I’ve been seeing on television for 20 years.” Not five minutes into the reception, Sokolove sidled up to her. “I think I’m falling in love with you,” he said. “Do you want to have a baby with me?” After that opening line, Sokolove didn’t speak to her for eight months. Then: “He came by the restaurant one day and put his arm around me and said, ‘How have you been?'”

Stephanie entered Sokolove’s life during a difficult stretch for him. He had recently divorced from his second wife, and, at 53, had been slowly edging his way out of his business, contemplating retirement. He was in the process of dropping down from 65 employees to just seven. Before they married in early 1997, Sokolove told Stephanie he wasn’t sure where his career was headed. “Look,” he said, “I got a couple bucks, but I don’t know what I’m going to do.”

By the end of the year, Stephanie had given birth to a daughter. It wasn’t long, though, before Sokolove realized that his quasi-retirement wasn’t going to take. He began consulting for firms that wanted to follow his lead. And as he saw other lawyers succeeding with his playbook, he began to wonder if his regional firm, for all its success, had accomplished everything it could have.

sokolove family

Sokolove and his wife, Stephanie—who owns the restaurant Stephanie’s on Newbury—at home in Newton. Moments after first meeting her, he said, “I think I’m falling in love with you. Do you want to have a baby with me?” (photograph by david yellen)

Beginning in 1999, Sokolove started to rebuild. This time he wouldn’t keep any cases for his own firm; he’d refer them all out. By 2003 he had nearly quadrupled his number of affiliates, from 14 to 50. Five years later, he has 400 relationships set up in all 50 states. And he’s not stopping there. Convinced he’s the vanguard of another change in the legal business, Sokolove is rolling out a marketing effort next month that seeks to add another 200 affiliates to his network. “It’s all about national branding,” Sokolove says. “If you’re a Realtor, you can’t exist unless you become part of a system. That’s the same thing that is going to take place in legal services—consumers want to have trust in a name.”

Until 2000, Sokolove had advertised only in New England, but to feed all his new and far-flung affiliates, he needed national advertising. As before, the vagaries of legal culture conspired to complicate matters. No other personal-injury firm had ever tried advertising nationwide, since the rules for what bar associations allow differ from state to state. In Iowa, for instance, a member of the firm being advertised cannot appear in the spot, while in Florida, a member of the firm must appear in it. To get around all that, Sokolove’s commercials now feature only the name of the firm in block text, the phone number, and an actor’s voice-over. The face that launched a million lawsuits is gone, but his name is everywhere.


Wherever he goes these days, Sokolove carries two battered folders in his leather shoulder bag. The first folder is for business, the second for everything else. Filed in the latter is a one-page list of goals, typed as dutifully as a high school book report. He prepared it for a life coach he recently hired to help organize his priorities. (“I sort of went through a thing when I turned 64,” Sokolove says.)

Turning his mind once again toward retirement, Sokolove has cut back his hours in the office by two-thirds, freeing up his schedule for some more-satisfying pursuits, including spending more time with his 11-year-old daughter and his wife, who in March will open her second restaurant, on Tremont Street in the South End. He’s also working with Stanford Law School to fund a philanthropic project, Roadmap to Justice, that aims to make the civil justice system more accessible to poor people. Sokolove says he’d be surprised if he doesn’t experience a “liquidity event” that would buy him out of his business within the next three years.

Sokolove’s commitment to getting more involved in outside pursuits led him to Manchester, New Hampshire, on a bright afternoon this fall for the second of two days he spent canvassing for Barack Obama. He’d given a good deal of money to Democrats—$250,000 over the past decade—but found a new thrill knocking on doors. Yet he couldn’t seem to prevent his thoughts from sometimes circling back to his business. “I told my wife how many people have front steps where you can fall,” he said, as his car rolled into a quiet neighborhood near the river.

Later Sokolove introduced himself to an elderly gentleman who was out walking his dog. “Not the lawyer on television?” the man asked. “I’ll tell my wife—she won’t believe it.” Before long, Sokolove had invited himself into the couple’s living room, where they were happy to answer his too-personal questions: What sorts of medications were they taking? Why was their retirement money in stocks and not bonds? (Sokolove has added financial mismanagement to his list of practice areas.) Standing up to leave, he and the man embraced in an awkward hug.

Outside, Sokolove was pleased. “Sitting in houses and talking to people. This is my father,” he said. He seemed to feel he’d just made the kind of old-fashioned connection that had always eluded him. Of course, it was something altogether different. What the lawyer from TV had forgotten was that he’d already been in that living room at least a hundred times before.


Staff writer Francis Storrs detailed the Beacon Hill exploits of con man Clark Rockefeller in the November 2008 issue.