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Donovan McNabb, Donald Rumsfeld, Jenny McCarthy, Liz Phair

donovan mcnabb

Donovan McNabb Quarterback, Philadelphia Eagles
Mount Carmel, Chicago (1994)

Playing Fields: As a standout quarterback for Mount Carmel, McNabb knew how to make an impression. One teammate, Matt Tennicott, reports getting this account from an opposing player: Sometimes when the future NFL Pro Bowler stood behind the center and went into his cadence to start the play, he would look across his offensive line and into the eyes of one of the linebackers for the other team. Then McNabb would interrupt himself with a quick laugh, “Heh, heh, heh,” before continuing the cadence and running the play. The move was more than a little intimidating. At six feet two inches and 195 pounds by his senior year, McNabb also inspired fear—though good-naturedly so—around the halls of the South Side all-boys’ school. Tennicott recalls McNabb approaching kids in the hallway as if he were an authority figure. “He would put on this big, booming voice, and be like, ‘Excuse me, boys . . . ,’ acting like he was the dean.”

Go-To Guy: Jim Docherty, a former religion teacher at Mount Carmel, recalls that McNabb was more mature than most kids. “You never had to stop Donovan in the hallway and say, ‘Tuck your shirt in, and get to class,’” Docherty says. “He was serious about his studies, serious about his sports [both football and basketball]. But not in a way that he didn’t have a sense of humor. When I picture him, I picture him smiling.” McNabb helped pay off his tuition by staying after school to assist with custodial work; he also attended religious retreats. Once, when a fellow high-profile athlete was causing dissension on the retreat, Father Tim Andres, then the school’s principal, asked McNabb to have a few words with the disruptive student. “Donovan was able to talk to him and really turn the retreat around for him, and for everybody there,” Andres says.

Well Positioned: Heavily recruited to play college football, McNabb went to Syracuse, where he had a good shot at playing quarterback, rather than being switched to another position. “His passion was quarterback,” says Tennicott. “Just the way he carries himself and he leaves the huddle, it’s evident. And it was evident back then, too.”  –M. A.


donald rumsfeld

Donald Rumsfeld Former congressman, corporate executive, and U.S. secretary of defense
New Trier, Winnetka (1950)

Harbingers: Rumsfeld got an early start in government, getting elected vice president of his junior class, and as a senior serving as vice president of the venerable Tri-Ship, a service organization for boys. In addition, Rumsfeld was elected to TNT, a prestigious honor society that chose its students on the basis of “outstanding service and participation in New Trier activities,” according to the 1950 Echoes, the New Trier yearbook. “He was supersmart, and just a fine guy,” says classmate Bill Ryno.

donald rumsfeld

Heroics: Ryno and Rumsfeld took a harrowing trip with a dozen or so other Boy Scouts to New Mexico the summer before their junior year. Flying in a chartered DC-3, they hit a pocket of turbulence and dropped nearly 1,000 feet in seconds. While the other Scouts started getting sick, Rumsfeld and Ryno helped distribute airsickness bags.

Playing Fields: Rumsfeld, who went on to Princeton, was a standout wrestler, winning his 145-pound class in the sectionals as a senior cocaptain but losing in a “disputed referee’s decision down state,” according to Echoes. The team, however, won the school’s first state wrestling title. Because of his size, football was more of a challenge for the teenage Rummy, as he was known. “He was always too small to be on the first or second teams, but he was always out there mingling with them,” recalls his freshman football coach, Jim McFadzean. “He used to get a big kick out of telling a story about me after high school—that I wasn’t a very good coach because I never played him.”  –M. A.


jenny mccarthy

Jenny McCarthy Playmate and actress
Mother McAuley, Chicago (1990)

Jenny from the Block: When the 1990 yearbook staff invited students to redesign the Mother McAuley school uniform, the winning style—a demure cardigan sweater and knee-length shorts—was worlds away from the va-va-voom version Jenny McCarthy unveiled three years later when, on hiatus from Southern Illinois University, she posed for Playboy’s October 1993 centerfold in a naughty McAuley knockoff.

Then again, McCarthy wasn’t the typical “Mac” student. “At an all-girls’ school, most of us were lucky if we brushed our teeth every morning,” says fellow Class of ’90 alum Jennifer Cotter Bolan. McCarthy, on the other hand, came to school perfectly turned out, blond locks curled in cascades of ringlets. Classmate Christine Martus Byrnes says McCarthy developed another trademark early on: “She had a big mouth.” Byrnes adds: “Like her crazy attitude on TV, that’s how she was in high school. I don’t think she’s changed a bit.”

Still, classmate Colleen Sullivan O’Hara credits McCarthy with being down-to-earth. “When you see someone who’s very pretty, you think that’s someone who watches her P’s and Q’s,” O’Hara says. “But she was so natural, you felt very comfortable with her. She made everybody very relaxed.”

McCarthy has a slightly darker recollection. In an earlier interview with Chicago, she called high school “the worst years of my life” and summed up her fellow McAuley students in three words: “short, braces, retainers.” As for her numerous afterschool run-ins with classmates (McCarthy recalled being followed home and beaten up): “It was a jealousy thing. It almost seemed like every girl thought I was sleeping with her boyfriend.”

Cheerleader, Heartbreaker? While McCarthy wasn’t as active in sports as her three basketball- and track-star sisters (she participated in choir and dance club as a freshman, and served as a preschool student teacher in her senior year), she did score coveted spots on the cheerleading squads at two local boys’ schools: for Brother Rice her junior year and St. Laurence her senior year. The once- or twice-a-week practices left plenty of time for a favorite afterschool activity, cruising the Orland Park mall (“Back then it was all about looking for cute guys,” she told the Sun-Times). As for boyfriends, “One always kept coming back,” recalls O’Hara, who cheered with Jenny at Brother Rice. “They dated one year, broke up, and dated again the following year.” O’Hara remembers the dark-haired ex as “very good-looking.” As with every budding romance, love was fraught with heartache. “My high-school boyfriend had Heather Locklear on his wall,” McCarthy admitted to the Tribune. “I cried so hard and made him tear it into a billion pieces.”  –J. W. 


liz phair

Liz Phair Rock star
New Trier, Winnetka (1985)

Phair Warning? To people who knew her in high school, Phair’s explicit lyrics on her breakout 1993 album, Exile in Guyville, were less of a shock than the fact that she was making music at all. “I don’t recall her ever being in music or theatre,” says Betty Brockelman, her adviser at New Trier for four years. “I saw no signs of that—none.” Phair was a good student who did well in mostly advanced classes. “I thought, Well, maybe she’ll be a doctor or a lawyer.” Phair went on to study visual art at Oberlin College in Ohio.

Indie Cred: Her official credits were mostly mainstream: student government, junior varsity cross-country, yearbook staff. “She kind of looked like a suburban soccer mom,” says Molly Bryant, a classmate who’s now an actor in Los Angeles. “She had really short hair, and she wore yoke sweaters and pearls. If you look back at her yearbook picture, she looks older there than she does now.” Mike Kelley, who was a classmate and friend, concedes, “There was an awkward side to her in high school. But she was cool.” He calls her “indie before indie was indie.” In those days, her singular vision came out in her art. Classmate David Clement recalls that Phair’s father, an esteemed doctor specializing in infectious diseases, had a collection of books at home featuring gruesome depictions of disease symptoms. “She would draw these pictures of people with really disfiguring illnesses,” Clement says. “In AP art class her senior year, she started drawing some of those pictures, and I remember somebody else in the class having to leave the room one time. It was more than a little disturbing.”

Chord Progressions: Clement, who started teaching her to play guitar, says Phair could be extremely disciplined. “I remember teaching her how to play a D chord in the beginning of her senior year of high school,” says Clement, today a singer/songwriter in New York. “That next summer when we were coming home from our freshman year of college she was showing me things I couldn’t figure out. She just took to it so fast.”  –M. A.


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