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CONFESSIONAL: Michelle Obama’s COS Turned To Dixie Chicks To Alleviate Election Night Pain

(Photo: Chip Somodevilla/Getty Images)

Betsy Rothstein Gossip blogger
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In the latest issue of Cosmopolitan, Michelle Obama‘s Chief of Staff Melissa Winter opens up about how she got her job and how she felt on election night in 2016.

The answer is: Bad. Very bad. So bad that when it was clear Donald Trump had won, she left the party abruptly and early and went to her car to drown her sorrows in the Dixie Chicks.

“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.” 

The Cosmo piece reveals how she first became involved in politics.

Winter’s brother had landed a summer political internship in Washington that her mother had to pay for — $3K. But he ultimately got a real paying job. So her mother forced her to take his place.

She went to work for Democratic Texas Rep. John Bryant.

After she graduated college, she moved to Washington to be a receptionist for then-Rep. Norm Mineta (D-Calif.). She later worked for then-Sen. Joe Lieberman (D-Conn.). Shockingly, she admits she wasn’t close to one of her other congressional bosses — Rep. Anna Eshoo (D-Calif.).

Who burns a bridge in Washington?

Not many people. But Winter had some sharp elbows for Eshoo.

“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.” 

A close friend urged her to meet Michelle Obama. The friend even flew her to Chicago, put her up in a hotel and soon Winter found herself in Obama’s living room.

Two weeks later she was working for her.

She says she often thought of Obama as a “girlfriend” instead of a “boss.”

Why did she stay on with Obama after the White House?

The simple answer is love.

“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.”