The Straight-Shooter

Playing Goliath may seem like an enviable role, but it’s not so easy when you’re defending a Fortune 500 company against an ordinary guy. This is a scenario Kelly-Ann Cartwright has faced again and again in 17 years of representing giant corporations. But when Cartwright is involved, Goliath almost always wins.

Physically, Cartwright is an unlikely person to play a giant. Graceful, with a slender frame, she tends to favor quiet suits in charcoals and pinstripes. There’s no bellowing going on, either. Cartwright’s professional demeanor is low-key, poised and sincere.

“Kelly-Ann is a no-nonsense sort of person, a straight shooter,” says Peter Prieto, a colleague at Holland & Knight’s Miami office. “If she tells you something, you take it to the bank.”

Last November, Holland & Knight’s then-managing partner Howard Melton Jr. appointed Cartwright as the executive partner of the Miami office. Her selection—she replaces Prieto, who now oversees the firm’s litigation section—marks the first time an African-American woman has filled such a prominent slot at a major South Florida law firm. Cartwright also serves on the firm’s directors committee.

In the courtroom, the corporate giants Cartwright represents have usually been accused of discrimination or harassment by employees. She says Miami jurors—many of whom belong to minority groups and may feel they have suffered discrimination at times—have an especially strong tendency to feel sorry for plaintiffs that strike them as average Joes, with kids to raise and bills to pay.

 “In employment law, when you represent management within huge companies, you have to overcome the David-and-Goliath feeling,” Cartwright says. Despite the local bias against her clients, when her corporate clients have not mistreated an employee because of factors like gender and race—and Cartwright says usually they haven’t—she almost always carries the day. The key, she says, is to convince initially skeptical juries that even though her clients are enormous companies, each is actually made up of lots and lots of average Joes, including the managers trying to run departments, make a living and go home to their families.

Born in Guyana in 1967, Cartwright had a strong work ethic instilled early on. Her father, Lance Gibbs, globally renowned for his accomplishments on the West Indies professional cricket team, taught her that “winning is a habit.” He pushed his children to excel not at sports but in education, Cartwright says. “We learned that if you have some talent, you work hard and conduct yourself in a professional manner, good things sometimes happen to you.”

Her family moved to England when she was an infant. When she was about 5, the family returned to Guyana for seven years, then moved to the U.S., settling for about a year in Long Island, N.Y., where close relatives lived. The cold was not to their liking and the family moved on to Miami, which remains home to Cartwright, her brother, Richard Gibbs, and her parents.

Cartwright earned a bachelor’s in finance and business administration, graduating with high honors from the University of Florida in Gainesville. There too, she completed her law degree, with honors, in 1991, and went straight to Holland & Knight, where she had worked as a summer associate during law school.

She says she liked the quality of the firm’s work and its “people-friendly” culture, with a welcoming atmosphere for lawyers of both genders and diverse backgrounds.

“Throughout high school and college, in my finance classes, at times I was the only black person,” she recalls. She could handle this (“I didn’t walk in and feel like, ‘Oh, my!'”) but was happy to find that Holland & Knight had long had its doors open to people of color. “I would not have to be the one to demonstrate how black lawyers perform,” she says. “It was a big selling point for me on the firm.”

Cartwright found two attorneys particularly helpful as mentors. Judith Korchin, a fellow Gator, was one. Marilyn Holifield, a Harvard-trained African-American attorney, was the other.

“Kelly-Ann doesn’t back down,” says Korchin, a partner at Holland & Knight. “She is a strong presence in a courtroom.”

Cartwright also found an invaluable mentor in the venerable figure of Chesterfield Smith, whom the firm’s Web site salutes “as the architect of the present-day Holland & Knight.” He filled the managing partner position from the firm’s founding in 1968 until 1983. A major legal and political force as the outspoken president of the American Bar Association, Smith made the first public call to investigate President Richard M. Nixon during the Watergate scandal. “He was a legend in the law,” says Cartwright. “He called for Nixon to resign, saying, ‘No man is above the law.’

“[Chesterfield] really nurtured the women and other diverse lawyers in the firm,” Cartwright says, adding that Holland & Knight was among the first firms to extend benefits to gay and lesbian attorneys.  She recalls that Smith, a fellow Gator as well, took her out to lunch during her first week on the job.

While visiting relatives in Toronto in 1995, she met her husband,
Dexter, a vice president for finance and administration at a telecommunications firm. They have two sons, Justin, 9, and Nicholas, 6.  Despite the heavy demands of her career, Cartwright achieves a respectable degree of work-life balance, finding time to sleep seven hours a night, read novels and avoid working too often on weekends. “That’s my time for my family. I spend a lot of time going to kiddie birthday parties and soccer matches,” she says.

Cartwright doesn’t have many spare hours these days, but in the past she has squeezed in time to volunteer as a Big Sister, and to serve as chair of the Miami Women’s Initiative, an internal Holland & Knight program dedicated to the professional development of its women attorneys.

She loves calypso music, and hopes someday to resume the piano lessons she took as a child. “I play at the same level as I did when I was 12,” she admits.

Her mother, Joy Gibbs, says her daughter always had lofty goals. “Initially, I think that she wanted to do medicine,” Gibbs says. “But then she changed because she likes to talk. She always had to have the last word.” All the talking didn’t get in the way of her studies, however. “When I would come home from work Friday afternoons,” says her mother, who at times worked in management for several airlines, “Kelly-Ann would have already finished her homework and started the laundry.”

Cartwright says going to medical school was actually more her mother’s idea; Cartwright herself had set her sights on investment banking. But she decided there was more opportunity in the legal arena in Miami. She started out in commercial litigation, took a few employment cases, and discovered it was a hot area with rapidly developing law.

She says she often has to educate juries about what categories of defendants have special protection under the law. For example, she says, it can be difficult for jurors to understand that a person who is diabetic or has epilepsy is not necessarily legally disabled. “Even though an average person will often automatically assume that such a plaintiff should be considered disabled,” she says, “they are not necessarily considered disabled under the law.”

With a plaintiff who does fall into a protected category, Cartwright’s challenge is often to “convince the jury that what my client did was not only legally permissible, but was also right. If a worker was late 500 times, then the reason they were terminated was not that they were African American or Hispanic or a woman. Although that plaintiff may have lost his job and faced considerable financial and emotional pressures as a result, the decision-making management employee also faces pressures. Permeating everything I do is trying to convey a sense of fairness.”

It’s a Goliath-size job.