Finding a flaw in the law to crack the tax man's back.

• Author: Gray, Tim
• Position: Raleigh, NC, tax lawyer Jack Cummings

Raleigh tax lawyer Jack Cummings has beaten the N.C. Revenue Department so many times in the last two years that it has to be close to crying uncle. In June alone, he bested the tax man twice in two weeks in the N.C. Court of Appeals. "People I talk to in North Carolina, former members of the Revenue Department, say, 'That guy always kills us,'" says David Brunori, legal editor of Arlington, Va.-based State Tax Notes, a national tax-law journal.

Cummings, 51, is the lawyer who convinced the U.S. Supreme Court last year that North Carolina's formula for collecting intangibles tax was illegal. The tax was levied on investors who owned stock in companies that did business outside North Carolina. Cummings' win eventually will result in $150 million in refunds, though the way it will be paid is still being contested.

Tax lawyers are the social misfits of the legal profession, stereotyped as brilliant but nerdy. Though he's worked in Raleigh for more than a decade, Cummings still has the air of a country lawyer who grew up in Rocky Mount and practiced there for 14 years. An August morning finds him in a short-sleeve white dress shirt with bright-yellow tape stripes. It's sensible attire for a hot day, but a breach of the unwritten rule that big-firm lawyers wear long-sleeve shirts, preferably solid white or light blue.

Cummings has a slight twang and is surprisingly softspoken. "A litigator usually has to be pugnacious, even obstreperous, in defense of the client's interest," says Tom Field, publisher at Tax Analysts Inc., which produces State Tax Notes. "Jack, to his credit, knows how to be a litigator, yet is quite a nice person."

Cummings came to tax law midcareer. He graduated from Duke in 1968 with a major in economics and finished law school at Yale in 1971. After clerking a year for a federal judge in Baltimore, he returned home to Rocky Mount. "I was going to be a criminal lawyer till I had my first case, and the crook didn't pay me. It was $200." He switched to general civil law, practicing with the Rocky Mount firm of Battle, Winslow, Scott & Wiley. In 1986, at age 40, he left to return to law school for a master's in tax law at New York University. When he finished, he says, "I was an older lawyer with expertise but no clients." Womble Carlyle Sandridge & Rice, the state's largest firm, hired him for its Raleigh office in 1987, and he works there still.

In 1991, while chairman of the tax committee of North Carolina Citizens for...