The Briefing

by Sean Spicer

  Sporting a mustache and often sucking on a pipe, Cliff Hobbins always came to class in his trademark, three-piece suit. A bachelor at the time, Cliff lived on campus. He was relaxed, fluid, and ready to pounce on the unprepared like a panther. A fan of Ronald Reagan and a conservative intellectual in his own right, Cliff would regale us with Washington lore and endless stories about politics. He once told us the story of a summer, spiritual retreat hosted by William F. Buckley Jr. at Portsmouth Abbey. The retreat was supposed to help attendees escape from the normal routine of daily life and focus on eternal things. So, the head of the Priory was perplexed when he spotted Buckley reading a newspaper.

  “Mr. Buckley, why are you reading the New York Times?”

  Buckley looked up at the prior and replied, “I am looking for heresies.”

  It was a classic Buckley quip, but it was also a classic Hobbins story.

  Cliff was unusually well connected in Washington and New York, mostly with former students who ended up on Capitol Hill or Wall Street. Noticing that I had an early interest in politics, Cliff called in a favor with the office manager of the Democratic majority leader in the U.S. Senate, George Mitchell of Maine, and set me up with a Washington internship over spring break. Mitchell was to bedevil and stymie the administration of future President George H. W. Bush. While it was an odd pairing for a young, budding conservative like me, Cliff understood that what I needed more than anything else was to experience Washington.

  In between sealing envelopes and operating the autopen, I rode the Senate subway, watched proceedings from the galley, and delivered papers to the cloakroom. I remember Senator Mitchell was gracious to a fault.

  At age seventeen, I found the Washington scene intoxicating, but I soon learned—along with the rest of the Spicer family—a lesson about the impact Washington’s policies can have on families like mine.

  Shortly after my internship, Senator Mitchell and the Democrats forced the George H. W. Bush White House to accept a measure in its budget deal that enacted a 10 percent tax on luxury items above $100,000. Popularly known as the “yacht tax,” it went into effect in 1991. Cliff Hobbins could have told Mitchell and the Democrats what would happen to any industry if Washington singled it out for punishment. He was a big believer in the axiom “You get less of what you tax and more of what you don’t.”

  U.S. production of $100,000-plus yachts had peaked at 16,000 in 1987. By 1992, it had fallen to 4,250. North Carolina’s largest luxury-boat manufacturer fired more than 1,000 people. But Rhode Island was hit the hardest with 12,000 direct and indirect jobs lost. The “yacht tax” that eliminated these jobs generated a measly $12,655,000 for the U.S. Treasury.6 “That’s enough to run the Agriculture Department for a little over two hours,” observed James K. Glassman in the Washington Post. “Meanwhile, the tax has contributed to the general devastation of the American boating industry – as well as the jewelers, furriers and private-plane manufacturers that were also targets of the excise tax that was part of the 1990 budget deal.”7

  The rich spent their money on other things. And instead of buying new boats, they started buying used boats. The luxury tax was a classic case of Washington stupidity that allegedly targets the rich but actually hurts working men and women.

  While this had a direct impact on my father’s livelihood, it also directly affected me. I spent my teenage years working in a boatyard prepping, maintaining, and cleaning boats. Because the rich were not buying boats, there were fewer boats to work on. And that meant fewer opportunities for me and people like me to earn a paycheck. Liberals always complain that tax cuts never “trickle down” to the working man—something that has been disproven for the umpteenth time by President Trump’s own massive tax cuts. And they never seem to understand that tax hikes trickle down to hardworking Americans trying to earn a living.

  The timing of this new tax couldn’t have been worse for my family. While my parents were excited to open my acceptance letter to Portsmouth Abbey, it came with a hefty price tag. Never revealing what a huge financial burden this was, my mother, who had raised three kids and served as the CEO of our family, entered the workforce. She was hired to manage Brown University’s Department of East Asian Studies.

  While I didn’t realize it at the time, the experiences of my adolescence were shaping me into the conservative I am today.

  During my senior year at the Abbey, Cliff Hobbins took several students—including myself—to New York City. He introduced us to some successful Wall Street executives who were Abbey alums. The biggest takeaway from our conversations was the rising importance of Asia in the global economy. More than one executive (and Hobbins concurred) made it clear that students who spoke Japanese and understood economics would be on the fast track to success. Many alarmist books at the time insisted Japan would soon surpass the United States economically, and everyone would live in a Japanese-dominated world. So, learning Japanese was, I reasoned, a smart investment for my future.

  As soon as I was admitted to Connecticut College—a small, liberal arts institution with a campus that has that classic, gray-brick, New England look—I immediately set my sights on being a Japanese language major. (Imagine that on Saturday Night Live. I wonder how good Melissa McCarthy’s Japanese is.) Then I encountered Japanese, with its subject-object-verb sentences, its three scripts, and the most complex grammatical structure of any language. It wasn’t long before I received a letter from the dean suggesting that my talents should be invested elsewhere. Apparently a “D minus” in any language is still a “D minus.” I didn’t have to think long or hard about where I belonged. I switched to “government,” Connecticut College’s version of political science.

  There were no larger-than-life figures like Cliff Hobbins among the Connecticut College faculty, but my professors certainly stimulated my thoughts. Almost universally liberal, they were so diametrically opposed to what I believed about God, the United States, and economics, that they forced me to re-examine, deepen, and argue in favor of my beliefs. By the time I was asked to join the government honors class, I knew I was a conservative who belonged to the party of Lincoln and Reagan.

  I was painfully aware there was another side to our classroom discussions that was never acknowledged. Today, we are used to seeing “political correctness” on campuses across the country, but I was shocked when I first witnessed it as a college student.

  Connecticut College had invited Dr. Louis Sullivan, then the secretary of Health and Human Services in the George H. W. Bush administration, to be our commencement speaker. But the college disinvited him when it learned the prominent black Republican did not hew to the liberal orthodoxy on abortion. The “open-minded, inclusive, and tolerant” liberal student body and faculty couldn’t tolerate that, which I thought (and still think) was the height of hypocrisy. Listening respectfully to alternative viewpoints is the very foundation of being open-minded, inclusive, and tolerant. In 2000, I had a chance to meet Dr. Sullivan at a Susan G. Komen Race for the Cure in Florida. I went up to him, introduced myself, shook his hand, and apologized for how my class had treated him.

  When I wasn’t studying, I was sailing with the Connecticut College sailing team on the Thames River. By my sophomore year, I had been elected as the team captain. The truth is, I went to college to sail, have fun, and learn, in that order. I was lucky I managed to do all three, especially since my early brush with politics often inspired other pursuits.

  I ran for freshman class president (and failed miserably), interned for a state legislator, and volunteered for a congressional race in Connecticut’s second district. As a volunteer, I wrote letters to the editor and drafted talking points for a Republican candidate who used a campaign budget of no more than $50,000 to challenge a well-known incumbent. We lost that election by roughly 5,000 votes—not a bad showing for an underfunded Republican running against a longtime, well-funded incumbent in a Democratic-leaning district.

  Most Connecticut College students spent part of their junio
r year abroad. My financial aid would not transfer to the overseas programs I was interested in attending, but there were opportunities in Washington, D.C., that seemed interesting. So, after my sophomore year, I attended a semester-long program at American University (AU). AU won me over for two reasons: I wanted to see politics up-close again, and the university accepted all of my financial aid and scholarships.

  During that semester, I started to love Capitol Hill, with its campus-like environment filled with bustling lawmakers and congressional aides as well as journalists and lobbyists who walked swiftly—and with their own distinct purpose—between the Capitol and the House and Senate office buildings. I had been bitten by the Washington bug. I loved every day I was working in D.C. even as I criticized how it functioned.

  At AU, I lived in a dorm with politically-minded students who spanned the ideological spectrum. My liberal friends loved to debate with me while my conservative friends confirmed that I, in fact, had a point and made sense. Somehow, we all got along, and many of those friendships have endured the test of time . . . and the test of politics.

  While in D.C. that semester, I applied for internships and received several offers. One was from a Rhode Island member of the House of Representatives, Ronald Machtley, which I should have taken. Instead, I interned at an office within the Office of Personnel Management that trained federal government executives to testify before Congress. Another Connecticut College student had enjoyed that internship and recommended it to me, but it revolved around research, not politics. I quickly realized I was not meant to sit behind a screen all day researching issues on LexisNexis.

  When I wrote my end-of-the-semester paper on the internship, I described the office, its purpose and operations, its triumphs and failures, and questioned why it existed at all. I even explained why I had hated it so much.

  I got an “A” on the paper and learned something valuable. I had followed someone else’s passion instead of feeding my own. So, during the winter break of my senior year, I went back to Washington, determined not to make the same mistake. This time, I accepted an internship with Senator John Chafee, former governor of Rhode Island. And working in D.C. had never been more exciting.

  Bill Clinton of Arkansas was heading to Washington as our forty-second president. The city was electric with anticipation. I sat at the front desk of Senator Chaffee’s office answering phones, welcoming guests, and helping arrange courtesy meetings for the senator with Clinton cabinet nominees. I took calls from luminaries like George Stephanopoulos, the new president’s communications director—the kind of political operative I could only hope to become someday (albeit as a Republican). I also got acquainted with Senator Chafee, a moderate Republican who was always impeccably dressed, courteous, and a gentleman of the old school.

  Senator Chafee had a soft demeanor that only the foolish mistook for weakness. After Pearl Harbor, he left Yale University to join the U.S. Marine Corps, fighting at Guadalcanal and Okinawa. When the Korean War broke out only a few years later, the U.S. military was desperate for seasoned leaders. But most World War II veterans—especially those who had endured and survived the long, hard slog up the island chains toward Japan under General Douglas MacArthur—were understandably reluctant to re-up for hard fighting in Asia again, this time on the Korean Peninsula.

  But not John Chafee.

  He returned to the U.S. Marine Corps as a rifle company commander. After being surrounded by 120,000 troops of the Chinese People’s Liberation Army, he and his fellow marines executed a masterful retreat at the Chosin Reservoir.

  I am not a William Spicer or a John Chafee, but I have always had a deep respect for those who have served in combat. I am in awe of their service as well as their courage in the face of danger and the unknown. Their incredible example inspired me to support the noble cause they lived and died to defend.

  At age twenty-nine, I earned a commission in the U.S. Navy Reserve as a public affairs officer. During my nineteen years in the Navy, I have traveled the world, including McMurdo Station in Antarctica; Guantanamo Bay, Cuba; Stuttgart, Germany; and Enköping, Sweden. I have served with outstanding Americans. They are selfless, dedicated, and talented patriots. I am proud to have served with them, and our country is fortunate that they wear the uniform. Joining the United States Navy was one of the best decisions I ever made.

  I confess, I never felt like I belonged in places with marble floors, high ceilings, and rare books in burnished bookcases—places like Portsmouth Abbey, Connecticut College, the Capitol, and the White House. And I never felt as prepared or polished as the people I met in those places who came from money, prep schools, and the Ivy League. Somehow, though, I always managed to “get in” and pursue my dreams.

  CHAPTER THREE

  LESSONS LEARNED

  Donald Trump was holding court. That’s the only way I can put it. Most politicians work the room, but this was something different. As Trump spoke with one major Republican donor after another, it seemed as if he was letting the room work him, as if these wealthy donors were getting a moment to present themselves one by one.

  The “room” was an outdoor patio at the Boca Beach Club in spring 2015. As he shook hands and patted shoulders, Donald Trump had the demeanor of a man running for office; he also had very definite ideas about what a Republican candidate needed to do to win the presidency after Mitt Romney’s failed campaign. But no one I knew took the idea of a Trump candidacy seriously. The tycoon had publicly toyed with running for president before, giving speeches in key primary states and making an issue out of President Obama’s birth certificate in 2011. As a private citizen, Donald Trump had attended the annual White House Correspondents’ Association dinner in 2011 (as a guest of the Washington Post, no less). He had to sit there while Obama—who had just released the long-form of his birth certificate—and comedian Seth Meyers trolled him with one jibe after another.1

  Soon after that dinner, some pundits speculated that Donald Trump would run for president. The next month, Politico and George Washington University conducted a national survey asking if Trump had a chance of becoming president. The results showed that 71 percent of Americans believed Trump had “no chance” of ever winning the presidency.2

  Standing at the donor reception in Florida that night, I thought back to that poll number and suspected it wouldn’t be too far off the mark if the same question were asked again. I looked over my glass and out at the donors still eager to talk with “The Donald,” as many of them seemed more excited to meet a celebrity than a potential future president. After all, he had never held political office before, and this country has only elected politicians and military heroes to serve as commander in chief. The odds of someone with a different background winning a major-party nomination for president were slim to none. The odds of winning a general election were even lower.

  Furthermore, we were in Florida. Sure, Trump has multiple properties there. But that state was already home to two powerhouse Republican figures: former Governor Jeb Bush and U.S. Senator Marco Rubio. They were both presumed presidential candidates and had strong name ID among Republican voters. They both had well-established, national donor bases and national networks of support for robust get-out-the-vote campaigns.

  Donald Trump had name ID, but it wasn’t as an experienced politician. While toying with the idea of running for president in 2011, he had an unfavorable rating of 64 percent—which by all political standards is glow-in-the-dark radioactive.3 And yet, the donors lined up and jostled each other for their moment or photo with the star of The Celebrity Apprentice.

  As I normally did at political events, I stood off to the side, sipping a glass of wine and making small talk with some of the donors. But at this event, I kept an eye on the man holding court. I marveled at the dynamics at play among the sea of donors and wondered if the polling numbers could be wrong—and if maybe, just maybe, a political outsider really could run for president of the United States. And I also marveled at the fact that the two of
us, both from such different backgrounds, ended up in the same room.

  Sailing has always been in my blood, which isn’t much of a surprise to anyone. It’s easy to fall in love with sailing if you grow up in Rhode Island. But sailing was more to me than just a challenging—yet enjoyable—sport. It was a love that my father instilled in me at a young age. Perhaps more importantly, he showed me how to navigate the waters—whether smooth or choppy—and how to maneuver the sails and read the wind while going upwind or downwind.

  Sailing was in my father’s blood, too. Mike Spicer had grown up in Newport, Rhode Island. It’s a beautiful coastal town that boasts some of the most talented sailors and breathtaking yachts in the world. It’s also known for its famous estates and ornate mansions. Although my dad was raised in Newport, he grew up a world away from the lavish parties at the New York Yacht Club and other magnificent venues on the island. The Spicers were part of Rhode Island’s working class, like most residents of the state. But my dad knew how to find honest work—and he knew how to find the joys in life that everyone, regardless of wealth or social status, can obtain. Sailing became a bedrock in our relationship. Out on the open water is where I learned how to work, how to play, and how to have quality time with my dad.

  Sailing was special to me, and I found time—and places—to sail anytime I could.

  During college, I was on the sailing team, and I spent two college summers working at a yacht club in New Orleans, Louisiana, which allowed me to get out on the water of Lake Pontchartrain every day. After graduation, I moved to Stamford, Connecticut, where I coached a sailing team. One of my students was a bright and energetic young woman named Lindley Kratovil. At one point, I mentioned to Lindley that I planned to go to D.C. at the end of the summer in search of my first “real” political job.

  Lindley informed me that her father worked in Washington.