At Home In The City

The city’s Marriage Bureau, like its kind everywhere, used to be charmless and bureaucratic, the last place you’d want to be on your wedding day. It’s very different now. It’s attractive, welcoming, well-run, and even a little whimsical. (Newlyweds can take pictures in front of a faux backdrop of City Hall—just like we did for this month’s cover photograph.) Many people contributed to the transformation of the Marriage Bureau, but it happened because Deputy Mayor Kevin Sheekey believed it was important and made sure it happened. And though it’s hardly a significant public policy achievement, isn’t it a wonderful statement of how New Yorkers should be treated on one of the most important days of their lives?

It’s also a small but telling reflection of Sheekey’s character. Not surprisingly, Sheekey is married himself. He and his wife Robin Caiola Sheekey originally met in first grade in Washington, D.C., and met again years after college. In 2001, Sheekey ran Mayor Bloomberg’s first campaign, and when the Mayor won—remember, this was in the immediate wake of 9/11—Kevin and Robin moved to the city from Washington with their infant twins, Samantha and Dillon. We interviewed the Sheekeys in January at their apartment on the Upper West Side and talked about their novel perspective as parents raising children in a city that Sheekey, who is one of Mayor Bloomberg’s closest advisers, helps to run. The twins are now inordinately pleasant and charming eight-year-olds. They let us talk uninterrupted for about an hour and a half!

Let’s say we’re old friends from D.C., and now I have two young kids of my own and am thinking about moving to New York. Based on your last eight years here, what would you tell me?

Kevin: If you live in Washington, it basically feels like you live in the suburbs. New York can seem like a big, scary city. When I started running the Bloomberg campaign in 2001, I was flying back and forth, and every Friday night I would get home and Robin would say, “If he wins, we’re not moving to New York.” And I would say, “Don’t worry, we’re not going to win.” That%uFFFD worked until the day in November when it was clear that we had won, and then Robin and I were forced to decide whether to move here or not. But the thing you quickly discover about New York City is that it’s actually a great place for little kids! I think that has a lot to do with the playgrounds. Our playgrounds are amazing. When I grew up, you had the alley. Playgrounds are so much better than the alley!

Now that the kids are little older, do you still feel as positively about raising them in the city?

Robin: It was the best decision we ever made. We’re having so much fun. And it’s not just the parks; it’s the museums, schools, friends, the convenience of everything, the whole deal.

Kevin: And I happen to think it’s going to keep on getting better because they aren’t going to get behind a car when they’re teenagers.

I would think that being a Deputy Mayor as well as a parent offers complementary perspectives on city life, and I wonder if there have been many times when you’ve thought, as a parent and city resident, Why can’t that be fixed or be improved? But then you put on your Deputy Mayor hat and you know the answer why.

Kevin: It’s the opposite actually. I happen to be in a great job working for a great mayor, and I go to work thinking there’s nothing you can’t do. I worked on Capitol Hill for 10 years, and there you’re never really addressing the issues of constituencies, not directly, almost never. Compare that with last night. At six o’clock we started mobilizing to help Haiti, and by eight o’clock this morning I had 30 great people in a room, put them in leadership teams, and everything came into place—outreach to the business community, relief outreach, staffing for the call centers, updating the website, getting the word out through social media, outreach to churches. It was amazing to see. By nine o’clock, I was off doing the next thing.

So working in local politics and living in New York hasn’t beaten you down yet?

Kevin: Oh no. This may sound a little shallow in the context of politics, but the city amazes me every single day. I feel like I will always feel like a tourist here. I was walking over to the East Side last week, returning my sister’s dog after we babysat it over the weekend, and I’m at 79th and Lexington, and I look up and think, I can’t believe I’m standing at 79th and Lexington. Look at this! How cool is this?

How do your kids perceive your job? Do they understand that there are unusual aspects to it, like that most daddies don’t speak to the Mayor all the time? What do they call the Mayor, “Uncle Mike”?

Robin: It hasn’t at all affected them yet. They’re just waking up to it.

Kevin: They’re mostly excited about the Mayor’s dogs than everything else. Bonnie and Clyde are the coolest part of the deal.

Robin: And the Mayor is Mayor Mike.

Kevin: There’s been a lot of good stuff over the years. When they were about six months old, they marched in their first parade with the Mayor. The Gay Pride Parade. In the stroller with the flags. I think Diana [Mayor Bloomberg’s girlfriend, Diana Taylor] carried one of them. This year they are actually studying New York City in their class. So Samantha decides to write about the Rockefeller Center Christmas tree, and on the day of the lighting, we went over there with the Mayor. They got to be in the back of the Mayor’s car, and then they got to sit up front when the tree was lit. How great is that?

What are some of the more ordinary things you like to do as a family?

Robin: We love to get to the other boroughs, especially for ethnic meals. I love Arthur Avenue [in the Bronx]. Hands down, I love going over there. We’ll go to Greek restaurants in Queens. One of the coolest things we’ve done as a family has been participating in programs like the Million Trees Campaign—just getting out there and planting trees together. We planted a lot of trees in the Bronx. I actually organized our whole school to go out and help, so we brought around 250 kids, parents and teachers. It was wonderful.

What are Dillion and Samantha like? What qualities come right to mind?

Robin: Dillon is creative, funny, shy initially, but not once you get to know him. He’s so caring. He’s not a rough-and-tumble boy. He’s a sensitive, artistic boy.

Kevin: Samantha is the more aggressive of the two, loves soccer, very athletic. Even her teacher said to us something like, “I just want to be Samantha Sheekey,” referring to her positive attitude and confidence. And Dillon is everyone’s best friend. Teachers love him. He gets along with boys and girls. Loves music, loves painting.

Robin: If there’s a commonality, I would say it’s how really nice and kind they both are. They’re just great kids.

How do the twins get along with each other?

Robin: They’re each other’s best friend. In terms of siblings, they don’t fight much. I don’t know if it’s because it’s a boy and a girl and they’re less competitive, but they don’t fight much.

Kevin: It is very difficult to put one in a time-out because the other one tends to run in and start articulating the defense: “He didn’t do it, and if he did do it he didn’t mean to do it.” “She didn’t do it. If she did do it, I didn’t see it.” They’re ready for the plaintiff’s bar association already.

What are some of your biggest joys and biggest challenges as parents lately?

Robin: Things are always changing as the kids go through different stages. But I’m trying to savor every minute right now because I feel like there’s a very big transition going on. They’re transitioning out of being young children. They’re becoming more independent every day.

Kevin: For me, it is basic DNA. As parents, we are fiercely protective of our kids. You want your kids to do well, you want them to have every opportunity, you want to make sure they work hard, you want to make sure they have the right friends, that they enjoy themselves, that they’re not hurt, they get what they need. But it’s a constant balancing act. You want to make sure your kids aren’t spoiled, you want to be firm but not too firm. I feel this intense, sort of animalistic need to provide for and protect my kids. And at the same time I wonder about how to implement those values correctly.

What advice do you have for parents starting out with twins?

Kevin: Patience is probably the single greatest gift you could give any parent, because at times they’re going to drive you crazy, and your job is to be the parent. Your job is to try to keep your composure and to try to keep working with them. With twins, you feel like you’re in a club, particularly when they’re younger. You see other people with twins—they’re in the club. And it turns out the club is getting bigger and it has nothing to do with it running in the family; it’s reproductive medicine that’s growing this club. And you should no longer ask someone with twins if they run in the family, because chances are they don’t.

Robin: And if they’re a girl and a boy, don’t ask if they’re identical. That happens more than you might think.

Kevin, you must have an overwhelmingly demanding job. And Robin you have a growing child photography business [see sidebar below]. How do you two work as a team to handle family time and parenting responsibilities?

Kevin: First of all, I’d say that I’m home for dinner every night, and Robin would tell you I’m never home for dinner. So given that, the truth is probably in between. For me, dealing with the city is much easier than dealing with the kids. I have management responsibilities at work. I sort of feel like the Vice Principal. But at home you have a cooperative relationship, and that’s a tougher deal. You’ve got to work together. You’ve got two sets of responsibilities, two folks bringing different ideas to the table at times. At work, adults are pretty good at taking orders, but kids tend to be a little more difficult. I don’t know that I ever feel stressed at work.

That’s an extraordinary remark coming from someone who, among other things, ran the Republican National Convention in New York in 2005. Really?

Robin: Kevin has a unique ability to come home in a good mood. He’s always on his Blackberry, but he can come home and be present and be with the kids. With that said, I do all the household work. He’s a great cleaner actually, but I do all the bills and the family stuff.

Kevin: The Blackberry is definitely a point of contention.

Robin: At the table. But joking aside, family is everything to us. It’s our priority over everything else. And we really do make an effort to eat together as a family as much as possible. We even take all our vacations with our extended family. It’s really something.

I know you’ve known each other for a long time. Where did this story begin?

Robin: We actually went to first grade together—we lived in the same neighborhood in D.C. My older siblings babysat for Kevin and his sisters. I’m one of six and he’s the oldest of three. He went to college with my brother at Washington University in St. Louis. And after that we started dating—that was the reintroduction.

Any recollection of knowing each other in first grade?

Kevin: No, we couldn’t even find the class photo.

Robin: But my siblings remember babysitting for Kevin.

Has he changed much since then? 

Robin: Yes! His parents described him as a quiet kid, if you can believe it.

Kevin: Let me explain that in this way: They both worked.


Want to Be in Pictures?

Before she and Kevin had children, Robin Caiola Sheekey worked as a development director for organizations like the Center for Science in the Public Interest in Washington. She has also long been an avid photographer, shooting events and portraits, and last year she launched Central Park West Photography, with a focus on families and family portraiture. For more info, visit