The Tax Man Skimmeth: Could I Trust an Accountant Who Once Stole $1.2M?

Mr. Rubenoff was dressed in black Dockers, a red permanent-press shirt and black loafers so long they looked like barges.

Though he said he was uncomfortable talking about his past, he answered nearly every question amiably as we sat facing each other in one of the particle-board offices. This, I thought, is a guy who can’t say no.

As it turned out, not being able to say no is exactly what fueled his legal troubles. He told me that when he met an attractive woman through Match.com, he was working crazy hours for the midsize White Plains CPA firm Maier, Markey & Menashi LLP, his weight had ballooned to an all-time high of 350 pounds and his self-esteem had plummeted to a corresponding low.

The long-divorced Mr. Rubenoff had “always had a penchant for enjoying the casinos,” but now, driven by what he called his midlife crisis and a desire to entertain his new girlfriend in style, he began hanging out at the Borgata in Atlantic City on weekends and even some weeknights. “It escalated as my head got crazier,” he said. “My ego needed to be stroked more and more. I needed people to perceive me as someone with money.”

In January 2007, he made his first “withdrawal” from Maier client DV Capital, the personal investment account of Arizona Iced Tea co-founder Don Vultaggio. When no one noticed, he continued, transferring about $90,000 a month into his daughter’s college fund and then moving the money into an account controlled by his tax and consulting business, Rubenoff and Associates LLC.

He had always lived comfortably, but comfort was no longer enough. “I was dating out of my league,” Mr. Rubenoff said. “All she knew was, I had a lot of money and I was spending it freely,” not just on gambling, but on lavish dinners, shopping, traveling, cocaine—which “just kind of went with the rest”—and a Cadillac for himself. “I’d walk into a casino and hear, ‘Mr. Rubenoff, what can we do for you?’ And people are looking at me like, ‘Who’s this guy who can bet this kind of money?’”

“I was in such denial,” Mr. Rubenoff said. “On the one hand, I was doing everything I could to save [Mr. Vultaggio] money. On the other hand, I thought, ‘I work hard, I deserve it,’ though I didn’t.”

In February 2008, Mr. Rubenoff was arrested and thrown into Nassau County jail. He pleaded guilty and repaid $450,000, and DV Capital took a lien on a commercial building that Mr. Rubenoff and his family own. He was transferred to the Groveland Correctional Facility in upstate New York, where inmates live in dorms and can move around freely.

“It looked like a college campus,” Mr. Rubenoff said. He walked four to five miles a day, lifted weights and dropped 100 pounds. The hardest part was not seeing his then-14-year-old daughter, who was angry and stayed away.

Sentenced to two and one-third to seven years, he was granted parole his first time before the board after serving the minimum. “I felt sorry, but I had it in the back of my mind that I didn’t hurt anyone,” he said. “I didn’t take some 90-year-old widow’s money and she’s out on the street. I took a billionaire’s money. But these were people who were good to me, and I abused and broke their trust.”

A fellow inmate introduced Mr. Rubenoff to a rabbi who approached Martin Cohen on his behalf. Mr. Cohen hired him to take his wife and mother on errands, then eventually moved him to the accounting office. “Martin is an amazing person, a giver,” said Mr. Rubenoff, a nonobservant Jew and CPA’s son who grew up in Mill Basin, Brooklyn. “He took me in without judgment, without question.”

Mr. Rubenoff’s lifestyle is far more modest than it once was. The waterfront apartment he once rented in Nyack has been replaced with a room in his sister’s Staten Island townhouse, and the Cadillac is now an MTA bus. He’s dating again, and he says he always tells women the truth about his past, because he knows they’re just one Google search away from finding out anyway. He says his 20-year-old daughter has forgiven him for the damage he caused to their family, and they are once again close. “I just want what everyone else wants,” he said. “My own apartment, a car, a relationship.”

“I don’t need to be the show-off I once was,” he said. “I don’t have to fly first class.”

Mr. Cohen believes that Mr. Rubenoff is a low risk for further misdoings. “Would someone in his mid-50s who went through what he went through and is out now for a couple of years want to risk going back to prison?” Mr. Cohen asked.