From satire to semicolons, Tom Regan ’51 was a faculty legend

Two generations of Andover students remember their own favorite Regan moments. It is their opinion that Thomas J. Regan was the greatest teacher of his time.

Wanda Mann ’90 recollected: "My very first class at Andover was Mr. Regan's English course and that round table in Bulfinch Hall quickly became my comfort zone. 'Sex on wheels!'  he would exclaim when someone had a really profound insight."

Lessons learned in Bulfinch 8 remain for years. As recounted by Zack Drench ’90 on Facebook: "Mr. Regan was the best. Not too long ago I was telling my wife about ‘Satire and Comedy.’ Something like, 'Oh man, that class was great. We got away with murder. We read Volpone by Jonson, and Congreve, and Pope, and Sterne--and then in the spring it was 20th century stuff like recordings of Bob Newhart's phone bits, but really we were just goofing off the whole time.' My wife's response was, 'So you remember everything you read 25 years later?' 'Yeah, but we were goofing off the whole time.' 'Really?' '...Dammit, Mr. Regan! You win!'"

A feature story on Phillips Academy in The New York Times on April 30, 1978, contains this paragraph: "It is a faculty that at its best has teachers of the caliber of Thomas J. Regan, a tall, almost gaunt Yale graduate of immense expression, who conducts a class of ninth-graders like Toscanini in front of a symphony orchestra. Pricking the air with a finger, bouncing from his chair, Mr. Regan, the chairman of Andover's English department, seems able even in an expostulation on dashes and semicolons to make an indelible impression on young minds."

In his classroom, Tom Regan wanted to make sure that his “vermin and harlots” avoided writing with the passive voice. One of those vermin, Gus Quattlebaum ’93, who now reads hundreds of scouting reports for the Boston Red Sox, still cringes every time a scout uses the passive voice. Upstairs, Tom is not feeling sorry for Gus. “Your work,” we hear him scold, “would benefit from my Nobel two-hour lecture on the semicolon."

His influence at Phillips Academy crossed departmental lines, of course. As director of Andover’s famous Teaching Fellow Program, Regan dished out advice to younger colleagues like Vic Henningsen ’69, who still savors the following:

1. When teaching two sections of the same course, always refer to the one you’re not teaching at the moment as “the Honors Section.”
2. When students in your 8 o’clock section complain that the 10:15 class got their papers back a day earlier, always tell the truth: “That’s because I like them better than I like you.”
3. You aren’t truly running late in a class when kids look meaningfully at the clock on the wall, but when they hold their watches to their ears and then bang on the dials to see if they’ve stopped.
4. Teenagers are the lowest form of life.

Tom Regan’s mark is all over the campus today, nearly 20 years after he retired. Two classrooms in Bulfinch have his name at their doors. ("But I never taught in either of them," he riposted.) Tom single-handedly edited the Andover Bulletin for three years. And, like most Andover teachers, Tom influenced dorm and personal life, as well as athletics--long jump and hurdles and soccer.  

The curriculum vitae reads, “Coach, Intramural Soccer.” This belies the way Coach Regan, angular knees and elbows, would suddenly appear at the start of daily practice, emerging onto the soccer fields of “Outer Siberia” from his adjacent house at 37 Holt Road. “It was as if Shoeless Joe Jackson had made his way through the tall corn-stalks to our Field of Dreams,” remembers fellow Cluster Soccer coach Doug Crabtree. Just as quickly, Coach Regan disappeared into 37 Holt Road “to criticize my urologist.”

Henningsen captured the quintessential spirit of Andover’s renowned “Czar of Cluster Soccer”: “Final afternoon of the fall club soccer season and the shadows are lengthening on the upper Siberia fields. Coach Regan, eager to complete the season, offered the following vivid account of the end of the fall term:

A fast breakaway, a terrific shot on goal, the ball hits the uprights, bounces up and over the goal, lands on the stone wall bordering Holt Road and bounces from there into the back of a pickup truck going down the road into the sunset. Coach Regan whistles the season to a successful close.”

For 21 years, Tom and his wife Geraldine ran dormitories:  Day Hall, Paul Revere South, and Stimson East. Their inmates knew all about the house counselor’s trick of wearing only one shoe when running up the stairs to quell a disturbance. The lads needed to hone their sense of timing.

Working summers at Jones Beach, Tom met Connecticut College ’57 student Geraldine Maher. Years later, when Gerri overheard Tom joshing that he first encountered and then rescued her as a Jones Beach lifeguard like Ronald Reagan, Gerri said, “Pffft! He couldn’t lift himself he was so skinny!” Gerri told Peter Gilbert ’72  that the first date was great, except he wore a bow tie. She didn’t like it. He lost the tie, permanently--and got the girl. They married on June 15, 1957, and, as their two adored sons Bill ’78 and Tim ’79 observed, when it came to Gerri, Tom “loved her madly” for 60 years. Geraldine, among her other innumerable donations to Phillips Academy over the years, became known and loved for her witticisms, calming generations of anxious if not terrified visitors at the Admissions Office.

In Andover Nation, Tom and Gerri made art history when they dressed up as “American Gothic” for the Addison Gallery’s 50th Anniversary costume gala in 1981, so as “to improve upon” Grant Wood’s 1930 regionalist classic. The likeness was uncanny enough that when Tom stared at Grant Wood’s real painting in Chicago’s Art Institute, guards and staff started pointing wildly, “That’s him!” The image kept reappearing, including during those years when Tom was editor of the Andover Bulletin--in the days when, doing extras like that, your reward was in Heaven, and you did it all alone. That meant riding herd on class secretaries strewn all over the planet, pleading after deadlines. Tom also found himself shooting and developing his own photographs for the magazine.

In the rare occasions when Tom and Gerri escaped their triple-threat life on campus, they could be found in jazz joints from Haverhill to Cape Cod. One of Tom’s proudest contributions to Andover life was successfully wooing progressive jazz bandleader and pianist Stan Kenton to George Washington Hall for a clinic by his entire band. He brought the iconic trumpet player Dizzy Gillespie to P.A., too. Tom played the cornet himself, and the standup bass, although he rarely mentioned it. He did admit that he was a “jayvee gardener,” but his sons attest that he shone as a varsity carpenter, quietly building lots of useful furniture. Once, he built a sedan chair to have students walk him around Flagstaff Court in 18th-century garb as Swift or Pope on their birthdays.

Tom and Gerri could also be found off-campus hunting down a good wine. The concept of wine connoisseur intrigued him. In 2002, two years after retiring from Andover, Tom once claimed he was “the world’s first customer” for Two Buck Chuck. His standard recommendation to anyone who was stressed: “Open a bottle of wine and put on Sarah Vaughan singing Easy Living.” 

Between the two of us, we have five children and they all had Tom for English, some as ninth graders and again as seniors. One of our kids did not supply specific anecdotes, “I just remember that I always liked being in his company,” he recalls, while others fondly churn them out.

With feelings of comfort and joy, generations of Regan-taught alumni, returning to campus, will continue to have their eyes peeled for a bony figure, perhaps sporting a Cambridge scarf, doing cartwheels in a loincloth around the bell tower at midnight.