Bill Dean has the superhero alter-ego thing down pat.

Heir and CEO of a giant electrical engineering and defense contractor that makes nearly $1 billion a year? Check. Thrower of epic parties featuring scores of scantily clad women at his Georgetown mansion? Check. Owner or part owner of a massive Miami beach house, a party yacht, a sports bar, and a newspaper? Check. Politicians on speed dial? Check.

Dean’s been a steady and generous donor to campaigns in the last decade, public records show. He and his company, M.C. Dean, have given more than $560,000 to federal, Virginia, and District pols, with more than $160,000 going to District races.

But it’s not Dean’s political contributions that have raised some eyebrows at the Wilson Building. It’s the fact that he’s the direct boss of Councilmember David Catania, the sharp-tongued lawmaker who enjoys a reputation as one of the more ethical councilmembers on an ethically challenged body.

Catania is M.C. Dean’s $240,000-a-year vice president of corporate strategy, where he oversees the company’s organizational development, compliance, legal, and government affairs issues (except for in the District). Yes, the same M.C. Dean that has various contracts with the city totaling more than $13 million in 2011, is currently fighting for a $100 million streetlight contract, and won a $50 million contract to build part of the new streetcar system. All of which is a set-up, say some of Catania’s colleagues, fraught with problems.

“I am a firm believer that if you work for a company that’s actually doing business with the government, that has contracts with the government, then that activity should be banned,” At-Large Councilmember Vincent Orange recently said in a TV interview.

Catania sounds more annoyed than a freshly bathed cat when discussing the nexus, or lack thereof, of his two gigs. (He indicates he thinks it’s impossible for LL to write this article without implying that Catania is in some way corrupt.)

“I’ve taken extraordinary efforts to divide these two worlds,” Catania says, saying he’s always recused himself from any potential conflict of interests, has kept himself “willfully ignorant” of M.C. Dean’s dealings with the city, and never speaks to Dean about council matters. “I don’t know how much more I can do.”

To be clear: LL has never seen a shred of evidence that Catania has done anything untoward to help any of his private employers. (Before becoming V.P. at M.C. Dean last year, Catania worked at OpenBand, a subsidiary of the company. Before that, he worked at the law firm Akin Gump.) Further, Catania has a well-earned reputation for being on the right side of ethical issues. He was the first to call for former Ward 5 Councilmember Harry Thomas Jr. to resign and took on Medicaid contractor Jeff Thompson, now at the center of the federal investigation into Mayor Vince Gray’s campaign, when Thompson was at the height of his powers.

Even so, Catania’s employment at M.C. Dean still looks iffy. Should D.C. really have a system where councilmembers vote on bills that affect how their employers, their employers’ partners, and their employers’ competitors do business here?

D.C. hiring and contracting laws, which Catania has voted on and suggested changes to, affect just about every major construction company in the city by setting rules on who firms can hire and subcontract with. That includes not only M.C. Dean, but its giant partners in other ventures, like Clark Construction or Skanska.

And your definition of a possible conflict of interest may be significantly different from the city’s. Two weeks ago, Catania voted in favor a bill to expand the number of seats on the airports board—a bill moved to appease Virginia Republicans and make sure the $3 billion second phase of the Metro Silver Line to Dulles was built. Catania also voted to confirm Gray’s pick for the new seat: D.C. Chamber of Commerce President Barbara Lang.

M.C. Dean has been a major contractor on the first phase of the Dulles rail line, and Dean is a member of the chamber’s board. But the D.C. Council’s general counsel didn’t see any problem with Catania voting on the measures because there was “no direct and predictable effect” on M.C. Dean’s finances.

(The potential for crossbreeding between council and outside employment isn’t limited to Catania. Ward 2 Councilmember and Patton Boggs attorney Jack Evans advocated for a convention center hotel that one of his firm’s clients ultimately invested in. Ward 3 Councilmember and constitutional law professor Mary Cheh has voted on budgets that include healthcare contracts between the city and her other employer, George Washington University.)

M.C. Dean has contracts with the Department of Transportation and the Department of Youth Rehabilitative Services, has worked on school construction, and recently won a contract with DC Water. Catania’s outside employment effectively mutes a good-government advocate and budget hawk on some important issues facing the city related to those contracts, like whether streetcars are worth their enormous cost.

Catania’s boss has been active in city politics and an outspoken critic against union-friendly labor provisions.

Two years ago, after Dean rented his company’s trucks and crews to Jim Graham to put up campaign signs, he told the Washington Post: “In Washington, it’s important that businesses stay involved, and one of the ways that you’ve gotta stay involved is that you have to be active in contributing to people that you can occasionally count on for support.”

Dean has helped finance ads against former Councilmember Carol Schwartz (largely because she supported mandatory paid leave), leased office space to Councilmember Michael Brown’s 2008 campaign at a rock-bottom rate, and funded a nonprofit that has pushed back against union-friendly changes to city construction laws. (Its former* executive director, Ted Trabue, is the District’s school board president.)

Dean says he never talks to Catania about workforce issues and doesn’t pay attention to how his employee votes. And indeed, Catania has voted for labor-related laws that Dean finds objectionable. But Dean acknowledges that some might see a potential conflict stemming from his outspoken views and Catania’s votes on issues related to those views.

“I understand what you’re saying, but then you can’t let councilmembers have jobs,” says Dean.

And Catania says the city shouldn’t create a system that curries to career politicians rather than professionals who are successful in the outside world. “People can speculate if they like, ‘Is this a good system?’,” he says. “I just ask to be judged on my record.”

If only it were that simple.

Photo by Darrow Montgomery

*This story has been updated to reflect that Trabue was not the school board’s executive director at the time of publication.