With a distinctive background and a unique competitive fire, David E. Roop has for three decades been one of Virginia’s top matrimonial attorneys. According to peers, Roop is both a sophisticated thinker and a scrappy lawyer, a unique and useful mix for his contentious specialty. He is regarded as one of leading experts among divorce lawyers on valuing closely held businesses and other private assets. He has earned certifications in financial-planning and asset-valuation - credentials most of his peers lack.

Moreover, of the nearly 4,500 lawyers profiled by Ten Leaders since 2002, Roop stands out for having a deeply strategic orientation, and for being a negotiator’s negotiator. “I was a chess player growing up, so I learned to anticipate, to see several moves ahead,” he says. “No question that’s reflected in how I practice law today.” Since he launched his own law firm in 2009, his leadership in the profession will likely grow in the years ahead.

The eldest son of five children in a family that moved frequently, Roop says he learned to be resourceful early on - “my parents were frugal, to say the least, so we had built-in ambition.” He spent his high school years in Baltimore, and went on to Notre Dame, “the only place I wanted to go.” Still, the young Roop, who felt some pressure to follow his father into engineering, had an early knack for “working hard at not working, trying to meet every girl on campus.” Eventually he switched majors, joining the so-called “Great Books” program, an intense focus on literature and philosophy that “put me with smart people discussing weighty subjects - I loved it, I learned to work and enjoy it.”

On graduation, with little more than a sense of adventure, he joined the Peace Corps, spending 18 months in the jungles of Zaire - “qualified to do nothing but teach English, so that’s what I did.” Returning to Baltimore, he went to law school (“I knew ultimately that’s what I would do”) and graduated in the top third of his class. “I was always drawn to the contest, the competition, so trial law was natural for me.” He adds, “No one hates losing as much as I do.”

Roop joined a litigation firm in Baltimore, trying all manner of civil cases - “You name it, I took it: food poisoning cases, accidental pet death claims.” He evolved to higher-stakes cases, spending four years defending other lawyers in legal malpractice cases. In 1996, he joined Condo & Masterman, where he was trained in divorce law by two other members of Ten Leaders. By 1999, he was made a principal; he had a leadership role in that firm and its success until he started his own firm in early 2009. Roop has been on the winning end of headline-making cases involving cohabitation, spousal support, immigration and domicile. Though he is mathematically inclined, he considers custody his strong suit; though he is more knowledgeable of family law and evidence than most litigators, he prefers to resolve matters out of court.

Clients will find Roop personable, self-aware and keenly observant. His wife, Anna-Marie Roop, is a Yale-educated lawyer; they have two children and live in Oakton. Roop is also an avid reader of fiction and is a strategic real-estate investor.