How I Became Michelle Obama’s Chief of Staff
When Melissa Winter was growing up, she wasn’t exactly sure what went on in Washington, D.C. But after taking over her brother’s politics internship before her sophomore year of college, she got a crash course in how government works - and found she loved it. Decades later, she met Michelle Obama and the two hit it off. Winter became Michelle Obama’s first hire of her husband’s campaign, and Winter’s worked for her - on two campaigns, in the White House, and now - ever since.
Growing up in Chicago, and then in La Jolla, California, politics didn't enter into my thought process at all. I wasn't exceptional in any particular way. Academics were challenging for me. I had a lot of tutoring going on.
My brother was very interested in politics. He got accepted into an internship program in Washington, D.C., that my mother had to pay, like, $3,000 for. Two or three weeks before my brother was to head to Washington, he found out he got another job, and that job was going to pay him. My mother said to me, “I've already paid for this program. It's non-refundable. You're going to Washington.”
This was after my freshman year [at Skidmore College], in 1986. I was an art history major. I was not registered to vote. I couldn't have told you any of the fundamental differences between a Republican and a Democrat. The one thing I did know about Washington was that the drinking age was 18. So I thought, OK, there's something about this little adventure my family is throwing me into that will certainly turn out to be fun.
[Through the program,] I interned with a Texas congressman, John Bryant. I loved that job. You have 435 members of Congress but each individual office is its own little microcosm. They each have their own sort of chief of staff, their own little hierarchy. It's very orderly. Each one is supposed to do sort of the best they can for [their constituents]. It resonated with me that you go to work every day and do the best you can for this particular group of people, and you go home and meet with them, and you invite them to Washington. I thoroughly enjoyed being a part of that. The next year, I wrote the office and said, “I want to come back, I want to be your intern coordinator. I would love it if you would pay me to work there for the summer.” And they did.
I moved to D.C. the day after I graduated college, in the summer of ‘89. There was a job placement office where you had to take a typing test. [I got hired] to work in [California Rep.] Norman Mineta’s office. I started out as a receptionist, and I made $14,400 a year. You have to make choices every week: “Am I going to pick up my dry cleaning or am I going to get gas in my car?” I was very lucky I had a mom who was very generous and picked up my health insurance the first few years.
Today, I think a lot of young people would say, “I'm not starting out as a receptionist.” But it was a great way for me to start out. I got promoted within my office from there and I ended up spending seven years with the congressman.
I never found the work hard because I found it fascinating. I loved watching Congress. It wasn't so much the policy side of it. It was the people side of it, the public service side. Norman Mineta, or my future boss, Joe Lieberman, really did help people. They helped veterans who had lost their Purple Heart get it back. They did real things that really affected people's lives.
I worked for [California Rep.] Anna Eshoo [as an executive assistant after that]. I’d been very spoiled. I had a very close relationship with Congressman Mineta. He treated me as much like a staffer as like a daughter. I found that I didn’t have that kind of relationship with Congresswoman Eshoo. It was a tough time. There’s nothing worse than waking up in the morning and not wanting to go into your job.
After a year, I ended up working for [Connecticut Sen.] Joe Lieberman. I was his executive assistant too. I began to realize what I loved was running things. I was moving him around, making sure he was getting a briefing book every night, getting his letters signed, talking to his wife, and getting [him] home to Connecticut. Every single night on his drive home, I’d connect him on the phone to his mother, who each and every night sounded like it was like the greatest thing in the world that she was on the phone with Joey. I planned his youngest daughter, Hani’s, bat mitzvah. I loved this guy. I loved his family. I spent 10 years with him.
Every single Tuesday from 1 p.m. to 2 p.m., the Senate breaks for caucus lunches, and it’s the one time of the week that your bosses will not call you. So during that time, I and three girlfriends had lunch every week. One of the members of my foursome was a woman named Alyssa Mastromonaco, who worked for then-Sen. Barack Obama. She started to wage this not-so-subtle campaign, saying, “I think my boss might run for president. I think you would like his wife.” And I laughed and giggled and thanked her so much, but said there was no way I was leaving working for a principal to go work for a wife. I wasn’t going to leave Washington. I loved Chicago but I wasn’t going to move back there.
Alyssa - what do they say? She persisted. She bought me a plane ticket to Chicago one weekend [and] put me up in a lovely hotel. She took me out for a fancy dinner. The next morning, she and I took a cab to the South Side of Chicago, and I found myself in Michelle Obama’s living room. We spent about two hours talking and something clicked. I went home and quit my job. Two weeks later, I moved to Chicago and was working for Michelle Obama by February 2007.
To this day, I don’t know what came over me. I’m not a risk-taker by nature. I am a rule follower. It was a risk because, let’s be honest, in January and February of 2007 when Barack Obama was talking about running for president, there was nobody in this country that didn’t think Hillary Clinton was going to be our next president. At least, no Democrats. I had read one of his two books and I spent two hours with his wife. Those were the two criteria by which I completely altered my existence.
She and I just really got along, and we had fun. We had some really good heart-to-hearts. But at the same time, campaigning is grueling. People are always trying to figure out what is the role of the spouse and how seriously do we take them? What we were seeing and feeling on the road was tangible, and people were responding to Michelle Obama.
We worked incredibly hard in South Carolina. When we won [the primary], that night, we sat in her room, and ate wings and French fries, and drank Champagne, and celebrated. There were plenty of times where I felt like I was driving or flying around this country with a girlfriend, as opposed to a boss. So much of our conversation could veer off into reality television, or what movies we've seen, or what books we were reading. I cannot imagine working for someone you don't like or don't respect.
I cannot imagine working for someone you don't like or don't respect.
After we won [the election in 2008], we got in this sort of surreal motorcade down to Grant Park. The first African-American president had just won and I had had an excruciatingly small part in making that happen by, hopefully, doing everything I could for his wife. I'm going to cry again right now thinking about it.
I moved to Washington the day after I graduated college because ultimately I wanted to work in the White House. It took me almost 20 years to do that but I did it.
At the White House, I came in as [Michelle Obama’s] deputy chief of staff. A large part of my job was taking care of the family. I made sure that the girls were enrolled in school, that they had internships in the summer and went to camp. I always was working for Michelle Obama the person, and then after that, I was working for Michelle Obama the first lady, because I didn’t do any policy. I oversaw all the correspondence that came out of the East Wing. It was very important to me that it sounded like it was Michelle Obama, and it was authentic to her, and it used language and was warm like she was as a person. I oversaw and worked very closely with the scheduling office to make sure that the schedule made sense to her.
We had this internal joke in our office that if she's ever in a bad mood, just put her in a room with children. She loves kids. And kids do crazy, unpredictable, funny things. We were at one event at Children's Hospital at Christmas time, and she asked the kids, “What should I get my husband for Christmas?” Their hands shot up, and one kid said, “You should get him a hot tub.”
Wherever she would go, I think people would forget about politics, whether someone liked her husband or not. She was a rock star. Our first trip to Africa, we went to Ghana. There was not one person left in their house, because [it seemed] every single person in Accra, where we were, had poured out into the street to see her. To see him. It’s unbelievable to see how people - the whole world - was affected by this presidency.
[On election night last year,] I had gone to a party at one of our staffer’s homes. I was watching what was happening on TV, and I looked at my host and I said to her, “I’m not sure you all understand what’s happening but I can’t be here anymore.” I left and I put the Dixie Chicks on in the car because I just couldn’t listen to the news. I got home, and I turned on my TV with no volume, and I watched. It was a pretty bad night. I was texting with Mrs. Obama, and when it became sort of clear to both of us what was happening, she said she was going to bed, and I said, “I will see you in the morning.” It was terrible. It was rough. The whole White House [staff] felt this physically, emotionally, mentally.
I stayed on with her because I love her. It’s as simple as that. I love her, I love her children, I love her family, and after staying with her for 10 years and seeing her through so many different phases of life, from hospital executive to first lady of the United States, it made absolute sense to me that I would stay in this job and try and navigate this next chapter. I don’t know that Mrs. Obama and I ever had a direct conversation [about it]. There seemed to be a mutual understanding between the two of us that I was going to stay.
I’m the chief of staff, and we have gone from a staff of 25 people to a staff of four. It’s obviously different. We have a woman who’s vastly important to the world and we all have to take on more responsibilities because really, there’s only four of us. It’s certainly been a bit of a learning curve to figure it out.
I stayed on with her because I love her. It’s as simple as that.
My role [basically] stays the same, in that I am vigilant about making sure she has a personal life and private time and family time and all the stuff with the kids. But I am now sort of the go-between, the intermediator between people in general and Mrs. Obama. So it’s much broader than it was before.
We spent an enormous amount of time figuring out: how does she continue her work with children, and Let Girls Learn, and education, and making sure kids eat right, and mentoring, and all the things she did that were so important to her in the White House? How do we use these unbelievable opportunities that we have, and, frankly, with less constraints than we did in the White House, make them work for Mrs. Obama in this next phase of her life? A lot of what I do is making sure that she has the opportunities to continue to do the work that is so important to her.
It is my hope that I will continue to work for Mrs. Obama for the next several years, while her youngest daughter is in school and while they live here [in Washington]. I love waking up every morning and feeling that each day is new and different. There’s endless possibilities and I don’t know how many people can say that about their work.
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