What 22 Trump Staffers Looked Like in High School

By
The Trumpland yearbook.

Life in the Trump administration often sounds like senior spring. There are no expectations, popularity is capital, and the uncertain future is terrifying. The stakes, of course, are higher, but it’s the teenage drama that’s addicting. Because all good reality-TV shows are carried by casts of grown-ups reliving the drama of their high-school years, here is Trump World’s cast of characters when they were fresh-faced teens.

Steve Bannon, former chief strategist

Benedictine College Preparatory School, ’72, Goochland, VA

Dance Committee, German Club, Monogram Club, Debate Team, Company Efficiency Award.

John Bolton, national-security adviser

McDonogh School, ’66, Owings Mills, MD

Had leading roles in The Fantasticks, Carousel, and Finian’s Rainbow.

Ben Carson, secretary of Housing and Urban Development

Southwestern High School, ’69, Detroit, MI

“In general I was a good kid … But once I reached the boiling point, I lost all rational control.”

Elaine Chao, secretary of Transportation

Syosset High School, ’71, Syosset, NY

“I was kind of shy, quiet, but I joined some clubs like yearbook and the theater.”

Michael Cohen, attorney

Lawrence Woodmere Academy, ’84, Woodmere, NY

Claims he grew up admiring Trump and read The Art of the Deal twice.

Kellyanne Conway, counselor to the president

St. Joseph High School, ’85, Hammonton, NJ

Crowned Miss New Jersey Blueberry Princess.

Betsy DeVos, secretary of Education

Holland Christian High School, ’75, Holland, MI

When her school didn’t have dances, she persuaded her parents to put them on, offsite.

Michael Flynn, former national-security adviser

Middletown High School, ’77, Middletown, RI

A surfer, “he’d go out in circumstances where others wouldn’t do it,” said a friend of his brother.

Rudy Giuliani, attorney

Bishop Loughlin Memorial High School, ’61, Brooklyn

“He looked like a little man, not a student, like he was dressed to go to IBM,” said a classmate.

Hope Hicks, former communications director

Greenwich High School, ’06, Greenwich, CT

Captained the state-champion lacrosse team and modeled for the cover of The It Girl, a Gossip Girl spinoff novel.

John Kelly, White House chief of staff

St. Mary’s High School, ’68, Waltham, MA

Yearbook quotation: “California or bust.” “It was all about his sense of adventure,” classmate Peter Muise said.

Jared Kushner, senior adviser

The Frisch School, ’99, Paramus, NJ

“There was no way anybody in the administrative office of the school thought he would, on the merits, get into Harvard,” said a school official.

James Mattis, secretary of Defense

Columbia High School, ’68, Richland, WA

“He liked to have fun, the same as the rest of us, but he was thinking way ahead. He had plans,” said a classmate.

Stephen Miller, senior adviser for policy

Santa Monica High School, ’03, Santa Monica, CA

Once jumped into a girls’ high-school track race to prove men’s athletic superiority.

Mike Pence, vice-president

Columbus North High School, ’77, Columbus, IN

Chairman of Fun Day Committee. “He could have been a stand-up comedian,” said classmate Jeff Brown.

Rick Perry, secretary of Energy

Paint Creek High School, ’68, Paint Creek, TX

Named “Most Popular” and “Future Homemakers of America Beau” by his class of 13 students.

Mike Pompeo, secretary of State

Los Amigos High School, ’82, Fountain Valley, CA

Twice named “Employee of the Month” at Baskin-Robbins.

Reince Priebus, former chief of staff

Tremper High School, ’90, Kenosha, WI

Keyboardist in rock band Conditional Surrender, which covered a Van Halen song at Battle of the Bands.

Sarah Huckabee Sanders, press secretary

Little Rock Central High School, ’00, Little Rock, AR

Member of the Latin Club, Troubadours, and Teenage Republicans.

Anthony Scaramucci, former White House communications director

Paul D. Schreiber High School, ’82, Port Washington, NY

“The cool guy then was John Travolta. And for me, that was Anthony,” said a classmate.

Jeff Sessions, attorney general

Wilcox Central High School, ’65, Camden, AL

“The football players were picking on my friend,” said a classmate. “Jeff stood up and said, ‘Leave him alone.’ ”

Rex Tillerson, former secretary of State

Huntsville High School, ’70, Huntsville, TX

Played drums in a rock band called Sons of Adam that covered “Hang on Sloopy” and “House of the Rising Sun.” 

*This article appears in the June 11, 2018, issue of New York Magazine. Subscribe Now!

What 22 Trump Staffers Looked Like in High School