Kevin Sheekey ʼ84:  GDS’S Knighted Hopper

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Kevin Sheekey ʼ84:  GDS’S Knighted Hopper
by Dina Elboghdady

Sheekey talks about a career “in the wings”

Kevin Sheekey’s path to knighthood started five years ago in a Frankfurt airport, when he read a newspaper article about how President Trump’s looming decision to withdraw from the Paris climate accord would create a huge funding gap in the fight against global warming. 

Within minutes, Sheekey ʼ84 was calling his billionaire philanthropist boss, former New York City Mayor Michael Bloomberg, with a proposal: What if Bloomberg’s charitable foundation pledges up to $15 million to cover the U.S.’s unmet financial obligation? The plan expanded. Since Sheekey and Bloomberg were already in Europe on business, why not unveil the funding pledge in Paris? 

And so it was that Sheekey found himself arranging a meeting within 48 hours between Bloomberg, French President Emmanuel Macron, and Paris Mayor Anne Hidalgo at the  Élysée Palace. The meeting led to a press briefing hours after the White House withdrew from the deal. Bloomberg, flanked by Macron and Hidalgo, told the world that the United States would fulfill its financial obligations under the climate pact, with or without Washington’s support.

In April 2022, the French government bestowed Sheekey with the Insignia of the Chevalier de l’Ordre National du Mérite, in effect making him a knight for his work on behalf of the landmark climate deal. The honor marks the latest in a string of career successes for Sheekey, who has earned a reputation as an astute political strategist after 25 years by Bloomberg’s side. It also offers insight into how Sheekey prefers to get things done: off center stage. “I basically view politics as a great stage play, and that’s not to take away the positive impact it can have,” said Sheekey, who joined GDS in 5th grade. “But I do enjoy watching who is good at it, who is bad, who succeeds. I enjoy being part of the production, but I’d rather do it from the wings.” 

Insignia of the Chevalier de l’Ordre National du Mérite

Insignia of the Chevalier de l’Ordre National du Mérite Credit: French Embassy Washington

Kevin Barr, who was Sheekey’s advisor throughout his High School years, was among the few dozen people invited to the private decorating ceremony at the DC residence of the French ambassador to the United States, Philippe Étienne. Barr described it as an “august” occasion. The ambassador’s praise of Sheekey was exalted, he said, and Bloomberg spoke of Sheekey the way a proud father would of a beloved son. 

“Kevin was honored and moved and, at the same time, so genuinely himself,” Barr said. “He’s always combined this wonderfully ebullient, outgoing, generous, deeply curious, fascinated, optimistic personality with a lot of integrity. … When he’s his warm, friendly self, it’s not an act. From the time he was a kid, he was that way.” 

 

“THE BLOOMBERG WHISPERER” 

The 56-year-old DC native grew up the oldest of three children in a civic-minded household. His father, Arthur, helped create the Department of Education in the 1970s. His mother, Kathleen, was legislative director at Common Cause for a decade. 

Sheekey said that his family and his GDS education taught him to care about his community and fostered his willingness to engage people, traits that served him well professionally. But it was his mom who gave him his big break in politics. Her Capitol Hill connections helped him land a summer internship with Rep. James Scheuer (D-NY) after his junior year at Washington University in St. Louis. 

On the campaign trail with Bloomberg in 2005, Dillon Sheekey rides on his dad’s shoulders.

“Don’t ever apologize for how you got into the door because, I’ll tell you, I’ve never seen anyone succeed because of who got them in,” Sheekey said. “That may not be true everywhere, but in most places, once you’re in, you have to work hard, think smart, and work well with others to succeed.” 

The internship paved the way for a 10year career on Capitol Hill; five years with Scheurer after graduation and another five with the legendary Sen. Daniel Patrick Moynihan starting in 1992. The four-term senator from New York was a notoriously tough boss whose office was always teeming with talent. Within a year, Sheekey went from managing the senator’s schedule to managing his 1994 re-election campaign. He kept climbing, moving on to serve as the senator’s press secretary and then his chief of staff. 

The run in Moynihan’s office was “the best professional education of my life,” Sheekey said. But he felt that he’d hit the glass ceiling on the Hill and started shopping around for a lobbying job, with an eye toward a media or finance firm in New York that wanted to build its Washington presence. “I stumbled across [Bloomberg LP] and it checked all the boxes,” Sheekey said. 

Michael Bloomberg hired Sheekey as chief Washington lobbyist in 1997 and tasked him with raising the company’s profile and dealing with its mounting regulatory demands. 

Today, a quick online search turns up dozens of articles about Sheekey. They mention his “blarney-coated candor” (The Atlantic), his tendency to “speak without periods” (New York Times), and always his trademark “tieless preppy look” (Esquire). Many also refer to his mischievous streak. Case in point: As a college freshman, Sheekey was elected dorm president promising frequent parties for all (New York Magazine). 

The headlines usually highlight Sheekey’s role as the architect of Bloomberg’s political rise from a little-known billionaire with a growing media empire to the three-term mayor of New York City and presidential contender.  

“The Bloomberg Whisperer,” one headline read. “Mike’s Brain,” read another. 

UPROOTING THE FAMILY, SETTLING IN NEW YORK 

When Bloomberg mounted his longshot bid for mayor in 2001, it was Sheekey who ran the campaign, despite misgivings about his boss’s chances of winning. 

In a joint interview with his wife, Robin Caiola, Sheekey told New York Family that he was commuting between Washington and New York in those early days. “Every Friday night I would get home and Robin would say, ‘If he wins, we’re not moving to New York,’” Sheekey said. “And I would say, ‘Don’t worry, we’re not going to win.’” 

But his outlook changed when the 9/11 terrorist attack devastated New York and the nation. “Kevin knew what to do with it politically,” Hank Sheinkopf, who worked for Bloomberg’s 2001 opponent, told New York Magazine. “Instead of talking about the towers falling they talked about leadership and management. … Kevin understood organically what had to be done. That’s a big skill.” 

It didn’t hurt that Bloomberg pumped $75 million of his own fortune into the campaign, switched parties to run as a Republican (a strategic move to avoid competing in the crowded Democratic primary), and won the coveted endorsement of his predecessor, Mayor Rudy Giuliani. 

Come January 2002, the Sheekeys were moving to New York with their infant twins in tow. (Dillon and Samantha are now sophomores at Brown University and Duke University, respectively.) They now call New York home. 

Kevin Sheekey (left) and Michael Bloomberg (right) lobbying for the climate in Brussels at the EU parliament

SLEEPING LIKE A BABY 

During the mayor’s 12 years in office, Sheekey considered exploring other career paths a few times: in 2003, when he felt restless at City Hall; in 2004, after he helped lure the Republican National Convention to New York and ran the event on behalf of the city; and in 2005, after the mayor’s re-election when he got an offer to run California Governor Arnold Schwarzenegger’s re-election campaign. 

But Bloomberg convinced him to stay and appointed him deputy mayor of government affairs in December 2005, a new post that enhanced Sheekey’s political influence. “He knows everybody on the Democratic side, particularly in Washington, and then he was my guy to do the city’s half of the Republican convention, so he got to know everybody on the other side of the aisle,” the mayor said at the time. 

Sheekey says he’s proud of the role he played in his boss’s success: reviving New York City post 9/11, turning around a dysfunctional public school system, and pushing for sustainability long before it was cool. Sheekey helped create Bloomberg’s PlaNYC in 2007, an ambitious, long-term, environmental agenda for the city that turned into a “passion project” for him.  His interest in sustainability has grown and evolved ever since, hence his effort to get his boss involved in the Paris climate accord in 2017. (Under President Biden, the U.S. has since rejoined the treaty. Bloomberg Philanthropies kicked in roughly $7.5 million during the Trump years.) 

Sheekey is not too disappointed in Bloomberg’s failed 2020 presidential bid either, even though he’d been urging his boss to run for years and managed his self-funded presidential campaign. “Our early polling for the Democratic primary never showed that Mike could win,” said Sheekey, who is known for his number-crunching prowess. “But he didn’t want to sit on the sidelines. He got in with a singular focus: defeat Donald Trump. We were determined that Mike would be the nominee or he would be part of the campaign that removes Trump from office.” 

Bloomberg, who ran as a Democrat, spent  $275 million of his own fortune on negative Trump ads that Democrats needed to win in the general election. And when Biden won the Democratic primary, Bloomberg spent a lot of money on the Biden campaign, $100 million in Florida alone. “Had Mike not run that campaign, it is my belief that Trump would still be in office,” Sheekey said. “So I can go to sleep at night, no problem. 

Today, Sheekey is global head of external relations at Bloomberg LP, splitting his time between New York and London for the job. A few years after Bloomberg left office in 2013, Sheekey briefly considered running for mayor himself, at his daughter’s urging, but decided against it. 

“Let’s just say my skills are better put to use electing other people, and making sure others don’t get re-elected,” Sheekey said. “Sam is still a bit upset. … Perhaps one day she will run and I can help run her campaign.”
 

Kevin Sheekey ʼ84:  GDS’S Knighted Hopper
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