Smart, Stylish and Sporty

Having won most of the races in her life, Diana Taylor is enjoying the end of this latest run as head of New York State Banking

Ilona Lieberman Photography

Greenwich Cove, early December 1964: Nine-year-old Diana Taylor is at the helm of a Penguin, determined to win her second race of a Frostbite series. “Ready to jibe!” she calls to her first mate, dad Doug Taylor. “Look out for that cat’s paw!” he yells, but it’s too late. Caught by the squall, captain and crew are unceremoniously dumped into the freezing cold water. “It took your breath away, but Diana kept her composure,” Doug Taylor recalls. “I had to stop her from swimming off to retrieve equipment that was floating away.”

“Unflappable” aptly describes Greenwich’s own Diana Taylor, the super- intendent of the New York State Banking Department, but perhaps better known as “Mayor Bloomberg’s girlfriend.” “No comment!” she says, regarding the Big Apple’s chief executive. She means it, too.

Although her relationship with Michael Bloomberg is a matter of very public record, Diana is definitely not the usual gal pal. While “brainy beauty,” an early tabloid headline, certainly applies, the right adjective for this homegrown success is “extraordinary.”

As banking superintendent since 2003, Diana regulates an industry with assets valued at $1.7 trillion, and which plays a critical role in the state’s economy and the personal finances of millions of depositors. In her office overlooking the Staten Island Ferry Terminal at the tip of Manhattan, the willowy brunette greets her visitors with innate charm and grace.

A very youthful fifty-one, at five-feet ten, she has presence, but her warm smile is genuine. Outside the picture windows, a beehive of construction activity looks like chaos. “One day something wonderful will emerge,” she says. “I love that about New York City.”

Acting on what she loves has served Diana well; it’s a message learned early from her parents Lois and Doug Taylor, Quebec natives who chose to live in Greenwich because of its active outdoor lifestyle. After graduating from Wharton, Doug worked for Union Carbide while Lois taught French at Greenwich Country Day where her children — Diana, Doug Jr. and Stephanie — went to school. The children grew up backpacking, horseback riding, ice-skating, playing tennis and sailing at Greenwich Point. The family belonged to the Greenwich Skating Club and the Riverside Yacht Club.

Family vacations were always sports-oriented. Summer visits to Quebec meant canoeing on the lake near the grand-parents’ weekend home. “Or we’d do a bareboat charter with the kids,” Doug says. Winter weekends were reserved for skiing in Vermont.

“We exposed them to every sport except golf,” her dad says, “which, of course, Diana needed to learn six years ago when she began seeing Mike Bloomberg, who’s an avid golfer.”

“My parents raised no duffers,” Diana says, explaining that “duffer” is sailing parlance for “landlubber.” The attitude, however, applies to challenges of every description. The Taylor kids, for example, were put on skis as soon as they could walk. Diana laughs recalling how she and Doug Jr., then age five and three respectively, did a complete 360-degree spin on a T-bar on their way up a mountain while their parents, right behind them, could only watch horrified.

The two eldest kids were best buddies right from the start; Stephanie, the much younger sister, now a registered dietitian and a stay-at-home mom, idolized her older siblings. Diana had many friends, according to her parents, but was equally happy to curl up with a good book. “She read all the classics,” Lois says, “and, as a family, we all loved Shakespeare.”

Rather than fighting, her dad says that Diana and her brother would argue intensely, typically over which one their parents loved more or the number of peas on each one’s plate at dinner. “We used to count them,” Doug Jr., now a psychologist, recalls. “There had to be absolute equity.”

Diana’s head for numbers emerged early. Lois recalls a math puzzle that stumped the entire family. “We went to bed, but Diana stayed up until 1:30 a.m.; she wouldn’t stop until she had it solved.” Later on, she would be drawn toward economics. “Its concepts are very visual,” Diana says. “You can distill anything into a graph and impose clarity.”

Doug Jr. describes his sister as “driven, in that she needs to give whatever she’s doing her very best shot, and the tougher the conditions, the better.” He suggests that those qualities emerged as an unusual reaction to a social reality of her childhood years.

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