Man vs. High School

One of Pittsburgh's most legendary delinquents returns to the classroom.

It was every teenager’s worst nightmare. At 5:30 a.m., Todd Gallagher’s alarm started chirping. Without opening his eyes, he crept through the dark hallway into his parents’ bedroom. His stomach in knots, he nudged the sheets and whispered, “Mom, wake up. You need to drive me to detention.” Charlotte Gallagher sat up in disbelief.

A rush of déjà vu suddenly came over her. “Todd,” she sighed, “You’re 33 years old. What are you doing getting detentions?”

Author Thomas Wolfe famously lamented that “You can’t go home again.” Fortunately for Todd Gallagher, he never got around to reading that book. In fall 2009, Gallagher not only went back home, he returned to the most terrifying place of all: high school.

Todd vs. High School

In the summer of 2008, the Pittsburgh native was living the dream in Los Angeles. As a TV producer and former writer for ESPN, Gallagher’s work had appeared alongside such literary icons as Hunter S. Thompson and Ralph Wiley.

His first book, Andy Roddick Beat Me With a Frying Pan, shot up the best-seller charts on In the book, Gallagher worked with professional athletes to answer offbeat, barstool-inspired questions about sports. For example: Could Andy Roddick beat an average Joe at tennis if Roddick had to use a kitchen skillet as his racket? How would a professional psychic fare in a rock-paper-scissors tournament?

Praise came from every corner. The Los Angeles Times called Gallagher “George Plimpton on acid.”

The self-described semi-sociologist became famous for his ability to answer even the most outlandish questions, but during his high-school career, all he had were “questions he couldn’t answer.” Tad Conlin, an old high-school friend, liked to remind Gallagher of his scholastic calamities.

Conlin, now a pharmaceutical salesman living on Mount Washington, called one night to catch up with his buddy and to bust his chops a little. Somehow, the conversation turned to the age-old fantasy that all adults have indulged themselves in at least once: “What if I could go back to high school—knowing what I know now—and do it all over again?”

Both joked about how they would attain Fonzie-level aplomb, but then Gallagher dropped a real bombshell. “I would get a 4.0, easy,” he claimed. Conlin nearly suffocated from laughter. “No way,” he said, insisting that the successful author was still the same attention-bankrupt prankster he knew from their days at Greensburg Central Catholic High School. “You wouldn’t even manage to get above a 3.0.”

“You want to bet?” Gallagher replied, throwing down the gauntlet. “Three thousand dollars says I’ll make honors.”

Conlin theoretically accepted the fantasy bet, and even took it a step further, adding a final stipulation: The winner must use his prize money to publicly humiliate the loser in any way he sees fit.

Student Demeritus

Conlin thought the bet was a piece of cake, and for good reason. Gallagher wasn’t just any normal scholar on his extended tour of secondary education in the early 1990s. A bright but troublesome student, he set records as a freshman at the prestigious St. Andrew’s School in Middletown, Del., a buttoned-up boarding school where Dead Poets Society was filmed. Just the wrong kind of records. Gallagher was less Robert Frost and more Bart Simpson. Gallagher in time-out at St. Andrew's, 1991.

“I set the record for the most demerits in the history of the school, which I’m proud to say still stands to this day,” Gallagher laughs.

The strict conduct system at St. Andrew’s conferred behavioral grades on a scale of A to D, as well as the rarely employed U, reserved for the most unsavory hooligans. Gallagher’s grade? “Double U. Only three people ever have achieved that.”

Ironically, when St. Andrew’s expelled the rambunctious 15-year-old, he had already been voted the student-body president for the following year.

See, Gallagher is a man of many contradictions. When you hear that he went on to be dismissed from Shady Side Academy before “miraculously” (his words) graduating from Greensburg Central Catholic with a 1.7 GPA in 1995, or that a former English teacher admitted to students years later that Gallagher’s behavior gave her frequent night terrors—you probably imagine an aloof, long-haired, flannel-shirted kid smoking cigarettes under the bleachers.

But you’d be wrong.

“Thing is, I never did anything truly bad,” Gallagher explains. “I was just a comedian. My main cultural influences were Mad magazine and movies like Airplane! and Naked Gun.”

While Gallagher had a fondness for organizing student protests against everything from homework to cafeteria food, he also was a varsity letterman in seven sports, a member of the chess club, school play, mock-trial team and newspaper staff. Oh, and he was a National Merit Scholar.

“I just refused to learn about anything I wasn’t interested in,” Gallagher explains. All I need, he thought, is a fresh start.

While researching schools in Pittsburgh, one in particular stood out—Trinity Christian, a small K-12 school in Forest Hills. Gallagher saw a close-knit community where he could feel safe. He called the school’s principal, Dale McLane, and asked to enroll. But there was a catch: Gallagher explained that he wanted to chronicle his time at Trinity with a single cameraman, Point Park University film director Kevin Kaufman, for a documentary about his experience (see trailer, below). In return, he promised to be a model citizen and a good example for the students. No protests, no pranks. He swore.

“At first, I thought he was crazy,” McLane says. “But he promised me that he was serious about getting it right this time around.” However, McLane still had to sell the idea to members of the community, many of whom had reservations.

“I had parents come up to me with worries that this was going to be like the movie Billy Madison—just a joke,” McLane says. “But I stood by my belief that everyone deserves a second chance, and I made it clear that Todd would be on a very short leash. He sent in his tuition like any other student.”

Fifteen years after escaping from high school, one of this area’s most decorated delinquents was returning for the fall 2009 semester. There was only one thing left to do to make the experience authentic. Gallagher called his parents: “Mom, get my old room ready. I’m moving back in with you.”

Return to the Scene of the Crime

Though Gallagher’s parents—Martin and Charlotte, both chiropractors—had moved from Todd’s childhood home in Greensburg to new digs in Shadyside, they kept their son’s room intact, adorned with Little League trophies, basketball plaques and Larry Bird posters.

“We were happy to have Todd back home,” Charlotte says. “He keeps us young.” However, the Gallaghers established ground rules: No messes, no noise late at night and no wild parties. Todd also promised Principal McLane that he would abstain from alcohol at all times for the whole semester.

Easy-peasy, I’m a grown man, Gallagher thought. But then, as the restless night before the first day of school sleeplessly shifted into morning, Gallagher was flipping around in bed like a carp on a carpet.

“There was an impulse to pull a Billy Madison and bust out my old AC/DC T-shirt and show up in a ’95 Camaro,” Gallagher says. “But I decided to go the conservative route.” After dressing in an Adidas polo shirt and khaki shorts, he stuffed an enormous Nike duffel bag full of books and scrutinized the brown-bag lunch his mother packed for him: oranges and almonds. Nothing spectacular. “She was a little rusty, too,”he says.

He checked and double-checked to make sure he packed his notebooks and index cards as his mother drove him to school. After hugging her goodbye, he was greeted with a smile and a nametag by second-grade teacher Melissa Swearingen, five years Gallagher’s junior. As Swearingen escorted the 30-something “senior” to his homeroom, a sea of students parted to size up the new kid. Gallagher started sweating through his polo. “At that moment, reality set in,” he admits. “Maturity went out the window. It was getting more nerve-wracking by the second.”

No Habla Español

Trinity’s oldest student was most nervous about one course in particular: Spanish I, a class primarily populated by freshmen. When Gallagher took Spanish in high school the first time around, his overall grade was a stunningly low 4 percent. “I scored a zero on the final,” he recalls. “Instead of answering the questions in Spanish, I filled in the roster for the 1985 Detroit Tigers. Then I took a nap.”

Gallagher’s second crack at the Romance language was no honeymoon, either. On only the second day, “Paco” (his Spanish pen name) forgot to come to class with his textbook covered, thus losing valuable extra-credit points. Vocabulary proved challenging, too.

A few weeks into the semester, Gallagher used his personal blog to publish this harrowing dispatch from the trenches: “The fact that I’m struggling to this extent in a class with all freshmen is all the more humiliating. The effortlessness with which the students process the information is mind-blowing to me. The teacher tells them a word in Spanish, it goes in their mind, and then comes out whenever they need it. The word goes in my mind, fights a battle with the warring factions in my brain, gets lost around five conversations I’m having with myself about five different topics, and disappears forever.”

Then there was the “Ryan McGuire incident.” We’ve all been there. One day, Gallagher forgot to finish the assigned vocabulary homework, but by some small miracle, his teacher failed to collect it. Every slacker’s fantasy. Gallagher’s leg shook anxiously underneath his desk. Every tick of the quartz clock on the wall was a new benediction. He started asking random questions to keep any fleeting thought of homework from floating into Mrs. Jackson’s mind. Then, just milliseconds away from the sweet toll of freedom, disaster struck.

“Young Ryan McGuire raised his hand,” Gallagher sighs. “He asked the teacher if she was going to collect our assignment.” Gallagher’s heart sank. The bell rang and a flurry of papers piled onto Mrs. Jackson’s desk. In the hallway, Gallagher pulled McGuire aside to pass on a valuable life lesson.

“Listen, Ryan,” he said. “Whether you have your homework done or not, reminding the teacher is a no-go. You have to look out for your fellow man.”

Even English, of all subjects, gave the heralded author fits.

“For someone who talked Andy Roddick into playing tennis with a frying pan, I sure could be having an easier time in my rhetoric class,” he blogged in September. Perpetually tired and growing frustrated, Gallagher started falling back on his old comedic habits to entertain himself. When his British-literature class was reading the Old English epic poem Beowulf, he stood up in the midst of a critical discussion and, in an attempt to be “intentionally moronic,” imitated a cheesy line from the movie adaptation, thumping his chest and screaming, “I AM BEOWULF!” The joke killed.

“It feels good to make people laugh,” Gallagher says. “As sad as this sounds, even as a 33-year-old man, you still have an impulse to be cool. You still get the same fears and nerves.”

Gallagher was winning friends quickly, but as the new-car smell of high school faded and the 7 a.m. alarms started grating on him, he began hitting the snooze button. Tardiness infractions piled up, and one morning in homeroom, his teacher, 23-year-old Robbie Schmidtberger, dropped off a yellow slip with a scowl. A twinge of nostalgia overcame Gallagher as he read the note: Detention. Wednesday. 6 a.m. His first thought? “My mom is going to kill me.”


A silver Range Rover pulled into Trinity’s empty parking lot as the sun was still struggling to raise itself over the lavender peaks of Forest Hills. Gallagher was reclined in the front seat, using his book bag as a pillow.

Suddenly, the door locks snapped open with unusual force. In the driver’s seat, Charlotte Gallagher silently exuded the I’m-not-mad-I’m-just-disappointed vibe that has been perfected by mothers around the world to heap shame on their children. “My mom was not happy about the detention,” Gallagher says. “At all.”

But a mother’s scorn was nothing compared to the humiliation of what came next. A few days after serving his penance in detention, Gallagher got the call he had been dreading: “Todd Gallagher, please report to the principal’s office.”

Gallagher was a veteran of these chit-chats, but this time was different. Principal McLane showed no signs of anger. His voice stayed low and genuine, and he asked Gallagher why his performance was tanking.

“It was the first time in my life where I felt like an authority figure actually cared about me,” Gallagher says of the meeting. “Mr. McLane is one of the most wonderful people I’ve ever met, and after that day, I knew I couldn’t disappoint him.”

Newly motivated by McLane’s sincerity, Gallagher buckled down and turned to an unusual study-buddy to help him conquer Spanish I: his 89-year-old grandfather John Ciotti. Whenever his grandson got stuck on homework, John stopped by to impart some veteran wisdom.

“He turned a simple collage assignment into a grand experiment with 3-D pop-up figures and movable parts,” Gallagher chuckles. “It was incredible experience working side by side with my grandfather. That’s when I realized that I lost a big chunk of my life not seeing all these important people when I was away from home."

Studying—which Todd had historically done in front of the television, if at all—became a family affair. Charlotte Gallagher made it her mission to drill Spanish vocabulary into her son’s head.

“Doing flash cards for Spanish class sent us back to grade school, but this time it was fun and, at times, hilarious,” she says. “I didn’t expect to be part of Todd’s life at this stage in his career.”

Gallagher drew inspiration from his fellow students, too.

“I was surrounded by the absolute nicest, funniest, most genuine kids imaginable,” he says. “I can’t believe these kids were even real.”

But that didn’t mean he was coddled. From day one, Gallagher’s fashion sense and outdated references were lampooned. Once, he brought up the original season of MTV’s “The Real World,” which premiered when most of Trinity’s students were in Pampers. Gallagher would retort sartorial critiques with, “I swear this shirt is cool in L.A.” Worst of all, the students dismissed Guns N’ Roses, one of his favorite bands, as “oldies.”

For an experiment in physics, Gallagher’s group was assigned with the task of dropping an egg from a perilous height without it cracking. Immediately, everyone in the group started scrawling math equations and sketching apparatuses that would protect the egg. Everyone except for Gallagher, who sat sheepishly on the fringe of the discussion. “I had no idea where to even begin,” he says.

Finally, senior student David Ecker looked at his dead-weight partner in disbelief. “Dude, how are you semi-famous?” he asked, motioning for Gallagher to join the group’s circle. Gallagher couldn’t have been happier with the diss.“Whenever people are comfortable enough to make fun of you, that’s when you know you are truly friends,” he says.

Gallagher on working out with Trinity's soccer team: "I was worried I was going to break the kids. Instead, they broke me."The students took him under their wing, tutoring him in everything from photons to pop culture. In return, Gallagher gave them real-world wisdom. He told them how he cold-called’s editor-in-chief and, with meager journalistic experience and no college degree, confidently asked for a writing gig; how he relentlessly left voicemails for hundreds of athletes and sports teams with pitches for his book.

“That’s the one thing they never teach you in school,” he explained. “The ability to pick up the phone and call someone you don’t know trumps everything. You don’t need connections if you have gumption.

“It’s OK to fail,” he continued. “The important thing is to keep pushing on.”

For the first time in his life, Gallagher started using his Mensa-caliber potential, acing tests and participating in class. But more importantly, he was finally smiling again. Saturated in the vapid, superficial Hollywood culture for years, Gallagher arrived in Pittsburgh rather bitter and introverted.

“Coming into this experience, I was absolutely at my lowest point I’ve ever been regarding my view of human nature,” he admits. “The school really turned me around as a person, and the kids reaffirmed my belief in people.”

Judgment Day

At parent-teacher conferences in November, Martin and Charlotte Gallagher couldn’t help feeling anxious as they sat facing Principal McLane. They had been conditioned to dread this time of year.

“We were very surprised by what Mr. McLane told us,” Charlotte says, choking up. “He spoke about how much Todd enriched the students’ lives. But all Todd ever told me was how much the students enriched his life. It was an incredibly heartfelt moment.”

In December, Gallagher gave his parents the best Christmas gift money can’t buy: a 3.8 on his report card. He had other news, too: He was selling his place in L.A. to move back to Pittsburgh to be closer to his family and the school that turned his life around, where he hopes he can continue mentoring.

The Gallaghers were ecstatic. But Tad Conlin wasn’t so thrilled.

“I’ve entertained many ideas about how to use my winnings,” Gallagher says of their bet. “I might take out some ad space and run a TV commercial featuring Tad’s most embarrassing pictures.”

Give the man an A+ for creativity.

"Todd Vs. High School": The Trailer.


Categories: Arts & Entertainment, From the Magazine