Who Thought This Was a Good Idea?
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I was not playing dress-up for the purposes of some obscure, political Halloween party, where everyone is instructed to go as a candidate from the opposing party and you play pin the tail on the majority leader. I wasn’t having an identity crisis or participating in an election-year cosplay convention. I wasn’t trying to pull a weird prank on my coworkers by tricking them into thinking my autumn look was Republican Mom, nor was I engaged in a top secret bait-and-switch mission designed to befuddle and take down the New York GOP. No—I had been called to serve.
I’ve known Chuck Schumer, the incumbent New York senator who ran against Long in the 2016 election, for many years. We met when I was working for Obama in the Senate, and we worked together a lot during the 2006 midterms—Schumer was the chair of the Democratic Senatorial Campaign Committee, and Obama was traveling so much on behalf of candidates that year. In many ways, Long was running a kamikaze campaign against him; in such a liberal state, she had little chance of taking the Senate seat he’s held for 18 years, and she’d already lost to one sitting New York senator, Kirsten Gillibrand, in 2012. The New York Republicans picked her as Schumer’s opponent because she was the only person willing to do it.
But even if you’re a shoo-in for something, you should always come prepared. About four weeks before the election, I got an email from Chuck Schumer’s office asking if I would be interested in playing Long in the mock debates he’d use to get ready to face the wall of her conservative proposals. I thought it would be fun, so I said sure.
I’d been in the room during debate prep before, but not as the challenger. I never jumped in during Obama’s sessions; the closest I came to the action was when I had to go to Neiman Marcus and buy 10 different red ties for John Kerry to test on camera—we had to see which one “burned hot.” So I dove into my own preparations head-on.
Chuck’s chief of staff, Mike Lynch, instructed me to keep my assignment top secret—I wasn’t even supposed to tell David, though I already had before they told me not to—and the team sent me a packet of materials to bone up on Long’s positions and style. They also sent me a list of questions a moderator might ask her—without the answers, so I could come up with them myself.
I had no idea how into it I’d get. I printed out five different types of documents, organized them in a binder, and wrote out my own glossary and index of questions. I watched videos of past debates to get her reactions down; I studied lists of remarks she’d made about various issues—health care, ISIS, gun control—and went over background research that I could use to support her views. I started off each day by reading her campaign’s press releases. After I noticed she seemed to do a fair amount of tweeting herself (you can always tell), I followed her on Twitter, and then I read her entire feed. I developed a deep understanding of her evolution from relatively subdued and respectful Christian conservative to full-on Donald Trump supporter, complete with effusive praise for Hero Julian Assange and an absolutist stance on the Second Amendment. She still doesn’t swear, though.
To top it all off, I analyzed her look. Chuck’s team told me I should “just wear an outfit from the White House,” but I got rid of all those clothes when I left—there was no way I was going to show up to work at VICE in an A-line skirt and a blazer, and I had no desire to. But at J.Crew, I went full on Professional Woman: navy blazer, navy pants, navy T-shirt. I paired that with navy shoes I had in my closet and the pearls I bought when I went to China with POTUS. The day of the debate, I even did my hair with rollers. (Wendy likes a lot of volume.)
When I came out of the bathroom, the worst possible thing happened: David exclaimed, “Oh, you look so nice!”
I met Mike and Lindsay Kryzak, Schumer’s head of digital, for a wholesome, Christian meal of chicken and gravy, washed it down with a bourbon on the rocks, and walked into the New School’s Tishman Auditorium ready to advance a hard line on immigration, binder in hand.
I felt reasonably confident on my grasp of Wendy’s positions—one aspect of her stance on gun control even made me a little sympathetic, for a second—but I was kind of nervous about my delivery. There were about 30 people in the audience, and I didn’t want to blow it—if Chuck somehow bombed his actual debate, it could have lasting consequences. He was in line to become either the majority or minority leader of the Senate.
We weren’t allowed to interact before, but I could tell Chuck was pleasantly surprised when they introduced Wendy and she turned out to be me—the last time we’d seen each other, David and I had met him and his wife for dinner in Williamsburg.
But if he thought I was going to go easy on him, he was mistaken. We approached each other and shook hands.
“Nice to meet you, Ms. Long,” Chuck said.
“Actually,” I replied, “it’s Mrs.”
“Oh, so that’s how it’s going to be.”
We were off. Chuck did great, but I held my own, even getting a little sanctimonious when the time was right. It was fun and creative—I said “Make America great again” at least three times, and I cracked a smile for only one of them. (Soon it wouldn’t be funny anymore, but at the time everyone else laughed, too.)
While we weren’t allowed to talk beforehand, I was too excited not to say anything to Chuck afterward. “That was so fun!” I told him as we shook hands for the second time. “Do you think I could be an actress?”
Chuck paused for a moment before replying. “No.”
When I left the White House, I was so worried: that I would never see my friends again, that I would never be successful on my own, that I had given up the one thing that made me who I was. But as I adjusted, sometimes painfully, to my new life, I realized both that I could live without it and that it would never really go away—not least because politics affects most, if not all, aspects of our lives.
Now, my involvement has become less about me and more about what I can do. I’m not talking about what I can “contribute”; I’m talking about how I can be a real, invested part of the country. In the days after the 2016 election, several former Obama staffers expressed the sense that, after they left the White House, they had believed they could just kind of fade away into the background of the political sphere, popping up as a surprise debate practice partner or podcast guest when it was convenient or fun. The results made it clear this was not the case: We will have to be active, resourceful leaders of a new movement. I am not a political beast; I don’t need to be working on campaigns or cycling through administrations all the time. But I can do a lot, and I know that I have to. Besides, if I’m being completely, totally honest, there are a couple of (female) politicians out there whose work I really, really believe in. If any of those women ever decided to make a big run for it, and if they thought I could serve them well, I would have a very hard time saying no.
While many people are disillusioned with our government and the political system that enables it, I just cannot think that way—even when it’s too frustrating, or upsetting, or terrifying to watch. Although I have no idea what will happen next, I do know that it would be a denial of everything I learned working for Barack Obama to give up or opt out. Politics will always be a twinkle in my eye—the thing that makes me say “What if?”
ALYSSA MASTROMONACO
Me and my Omie in our fabulous coats. I have binoculars because she loved to look at birds.
CLAY DUMAS
Me channeling my inner Diane Keaton in preparation for my interview with Charlie Rose.
PETE SOUZA
Before “Alyssa and Kathy’s Last-Chance Dance,” the White House threw us a cocktail party to celebrate our last day. This is the Oval Office back patio; that’s Kathy talking to POTUS.
PETE SOUZA
The entire scheduling and advance team freaking out on election night at Grant Park. I went home early to get some sleep, so I’m not in this photo, but the guy in flip-flops is having enough fun for the both of us.
MARVIN NICHOLSON
The coolest I’ve ever looked, on Marine One across from POTU
S.
ARUN CHAUDHARY
Marv and me on NightHawk 2 on our way to see the launch of Space Shuttle Endeavour on April 29, 2011. It was canceled due to an equipment problem, but I got another slick sunglasses photo out of it.
PETE SOUZA
This is the reception for Plouffe’s last day. I’m telling a very funny story.
LAWRENCE JACKSON
White House Chief of Staff Bill Daley once told me he would like to “burn those pants” and that they looked like something Rodney Dangerfield would wear. I loved them.
PETE SOUZA
POTUS, WH Chief of Staff Denis McDonough, me, and Deputy Chief of Staff for Policy Rob Nabors in the Oval. Denis looks good.
PETE SOUZA
Me resisting POTUS’s attempts to antagonize me with my thirty-sixth birthday gift. (It was a really beautiful rose gold bracelet.)
PETE SOUZA
Everyone breathlessly anticipating whether I will poop on the pope.
PETE SOUZA
Pfeiffer, POTUS, and White House Press Secretary Jay Carney told me I was the size of a hedgehog, so I was pretending to be a hedgehog.
PETE SOUZA
In the middle of our 2009 trip to Iraq, we had to change plans midflight because a sandstorm was rolling through. This is the conference room on Air Force One; I had secret plastic bags in my jacket pockets in case I needed to puke on the helicopter.
PETE SOUZA
POTUS drops in on me, Joe Paulsen, and Bobby Schmuck having a meeting in my office. Note my zip-up fashion hoodie.
PETE SOUZA
Me, POTUS, and Deputy Chief of Staff for Policy Mona Sutphen on our way back from Ghana.
PETE SOUZA
My sister and me with POTUS in New York. I routinely wore sequins to work.
CHUCK KENNEDY
Smoot and me outlining our plans for a fund-raiser at Paris Fashion Week in 2012: Kanye West would be there, and I was going to get to the bottom of whether he was really dating Kim Kardashian.
PETE SOUZA
POTUS receives an update on Hurricane Sandy at FEMA headquarters. FEMA Administrator Craig Fugate is on the right.
PETE SOUZA
Messing around on Marine One with FLOTUS (who looks great), FLOTUS’s Chief of Staff Tina Tchen, and Jay Carney.
PETE SOUZA
“Do you like the debt ceiling? Check box Y/N.”
DAVID LIENEMANN
Marv, VPOTUS, my messy desk, and what is possibly an issue of People magazine.
JASON REED/REUTERS
Me, Plouffe, and Favs on the campaign trail in summer 2012, trying to figure out if the diner across the street is open.
LAWRENCE JACKSON
November 22, 2013: me, David, and Supreme Court Justice Elena Kagan picking out our wedding vows in her office. The bride wore Stella McCartney in petrol blue.
Acknowledgments
If it weren’t for my parents, I would have dedicated this book to Possum and Plouffe. A part of me regrets giving up the opportunity to make them very uncomfortable by doing so. I can’t thank them enough for all they’ve taught me.
I would also like to thank:
• Cara Schembri, for being the best friend, mom, and feminist I know;
• Danielle (Dey) Crutchfield, Jess Wright, and the rest of Team SkedAdv, for always saying yes and proving that family comes in all different packages. I hope this book begins to honor your work and commitment;
• Amy Volpe, for enduring early-twenties me as a roommate, for making me live up to my potential, and for always bringing me back to reality when necessary;
• The rest of the women who show me how to be: Lea Goldman, Mindy Kaling, Amanda de Cadenet, Sophia Amoruso, Chelsea Handler, Jennifer Justice, Penny Pritzker, Nancy Dubuc, Audrey Gelman, Annie Karni, Hildy Kuryk, Jennifer Gonring, Rachel (and Rubes) Sklar, Amie Parnes, Julie Frederickson, Janet Mock, Kirsten Gillibrand, Kate Bernstein, Jocelyn Leavitt, Rachel Shechtman, Alex and Vanessa Kerry, Amel Monsur, Ciel Hunter, Kim Kelly, Elisa Bluming, Cathy Simmons, Kate Fleck, Lauren Frankle, Anne Finucane, Lisa Halliday, and Helen Brosnan;
• Little Axe Salon, for filling my life with good hair days;
• Dr. Bonn, Doc Jackson, and Dr. Goldberg, for giving my gastrointestinal and gynecological stories happy endings. Additional praise goes to Tampon Queen Molly Hayward for making Cora a reality. Lauren Talarico also deserves a medical shout-out for being the only veterinary neurosurgeon I’d trust any cat I love with (and for making me a god-mommy);
• Brat, Megara, Sam, Jill, Grodi, and Fogel, for loving me despite the fact that I was in college and kind of a mess;
• Nancy Ashbrooke and Alex Detrick, for welcoming me at VICE;
• Michael Smith, for making sure my hair wasn’t too puffy for Charlie Rose and for taking care of me after I left the White House;
• Tina Tchen and Valerie Jarrett, for showing me how to be a woman at the White House;
• Kathy Ruemmler and Peaches DeParle, for being like sisters;
• Julianna Smoot, Anne Olaimey, and Stephanie Cutter, for looking out for me when I didn’t know how;
• Reggie Love, for teaching me why people should play team sports;
• Charlie Rose, Maneesh Goyal, and Samantha Jacobson, for showing me that I don’t always have to be behind the scenes;
• Melissa Winter, Laurie Rubiner, Lona Valmoro, and Tovah Ravitz-Meehan, for taking me in;
• Joe Paulsen, Bobby Schmuck, and Eugene Kang, for knowing exactly what I needed, when I needed it;
• Anita Decker Breckenridge, for winking at me when no one else would;
• Clay Dumas and Dan Brundage, for supporting me in every way possible throughout my time in the White House and after, and for not being judgmental when I lost my shit over fucked-up grilled cheese sandwiches;
• Jon Favreau, for always being there (and down for Ruby Tuesday);
• Robert Gibbs, for being my ally, and for getting Bruce Springsteen to call me;
• Marv Nicholson, for teaching me to enjoy the simple things in life, like predicting the temperature and to always be kind;
• Dan Pfeiffer, for his encouragement, friendship, and trust, without which I would not be the person I am today (I would also be much worse at Twitter);
• Ferial Govashiri, for her bottomless generosity, for thinking I had style, and for speaking Farsi to Shrummie;
• Deb Futter, Sean Desmond, and Rachel Kambury at Twelve, for never giving up on me (even if they probably wanted to);
• Lauren Oyler, for helping make this book happen (and for being one of the smartest people I will ever know);
• Pete Souza, for the memories and for letting us print some of them here;
• Joe Biden, for being, as the memes suggest, one of the best dudes out there;
• Barack and Michelle Obama, for everything;
• David, for being the best guy who always puts us first;
• Petey and BunBun, for only sometimes peeing in the shower;
• And Shrummie.
About the Author
ALYSSA MASTROMONACO is president, global communications strategy and talent at A+E Networks. Previously she served as assistant to the president and deputy chief of staff for operations at the White House from 2011 to 2014 and as assistant to the president and director of scheduling and advance at the White House from 2009 to 2011. She worked for Senator Obama on his campaign and in his Senate office and PAC beginning in 2005. Earlier in her career she was director of scheduling for Senator John Kerry’s presidential campaign in 2004 and before that was press secretary for Congressman Rick Boucher. She is also a contributing editor at Marie Claire. Ms. Mastromonaco received a BA in political science from the University of Wisconsin–Madison in 1998.
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