Walt Ryba:

Good Sport & Good Business

Fellow students at Ridgefield High School knew that Walt Ryba would be a future leader. After all, the recently arrived Ridgefielder  had, by his graduation in 1959, been president of his sophomore, junior and senior classes, and co-captain of the football, baseball and basketball teams.

In fact, the Class Will gave “Walt Ryba’s many abilities and class leadership to future senior class presidents.”

It also gave his “oinky Studebaker to anyone who doesn’t like fast cars.”

His abilities and class leadership — not car choices — led to a lot more, and 40 years later, Dr. Walter George Ryba Jr., was dean of the School of Business at Fairfield University, where he was also professor of business law. 

Dr. Ryba (pronounced Ree-ba) was born in Stamford in 1941. His family moved to Craigmoor Road when he was a freshman. Learning that he had been active in youth sports in Stamford, RHS Principal Kip Holleran quickly signed up Ryba  for the baseball, football and basketball teams. He played end on the school’s first 11-man football team, was a basketball forward known for his “stylistic jump shot,” and as catcher for baseball, was “a mainstay of the team.” He was a leading hitter in the Housatonic League and named the high school's MVP in 1959.

Ryba went on to Dartmouth where he played baseball and football until a severe injury ended his college athletic career, but not his educational pursuits. After graduating from Dartmouth in 1963, he earned a master’s degree in economics at Trinity College in Hartford in 1971 and a law degree from the University of Connecticut in 1975.

Dr. Ryba began teaching at Fairfield University in 1982. He specialized in business law and regulation, focusing on antitrust regulated environments and international regulation, and his research appeared in many professional journals.

In 1994, what had been an academic department at the university became a separate school, offering a master of business administration (MBA) program. Three years later Ryba was named acting dean and the following year, dean.

He and his wife, the former Geraldine Pannozza — his high school sweetheart from the Class of ’59 — had been living in Lyme for two decades. As Ryba’s workload increased, the commute to Fairfield — as much as three hours coming home — became too much and the couple bought a house on New Street in their old home town.

At the school, now called Charles F. Dolan School of Business, Dr. Ryba made many changes. Under his leadership, the university added concentrations to the MBA in e-business and health care management, introduced a master’s in management of technology — offered jointly with the School of Engineering — and joined a consortium of Jesuit universities offering an MBA program at Peking University in China. He opened sites for MBA courses in Greenwich and Stamford and  added an “Executive MBA in Community Banking,” the first of its kind in the nation.

Dr. Ryba also oversaw the school’s final approval of accreditation and its move to the former campus Conference Center, which was completely renovated to accommodate the school’s expanding programs.

All the time, he continued to teach at least one course a year to maintain close contact with the students. 

“His door was always open to students and faculty,” said his wife. “As a result, he brought home a lot of work. He used to stay up till 1 o’clock in the morning doing work. But he loved it, he absolutely loved it. And he had so many plans.”

Dr. Ryba’s energetic leadership was tragically cut short. In August of 2000, he was stricken ill at his home and died shortly afterward at Danbury Hospital. He was only 59.

 “Walt Ryba was honest, straightforward and always used good judgment,” said Dr. Orin Grossman, academic vice president of the university at the time of his death. “His contributions to Fairfield University and particularly the School of Business will have a lasting impact.”

A year later, the Walter G. Ryba, Jr. Scholarship was established   to honor him by benefiting  multicultural students who have shown significant leadership in academics, student activities and athletics in high school. The same year, the Ridgefield Old Timers Association honored him posthumously for his excellence in athletics and education.

While much of his life was devoted to work in education, Walt Ryba also had more than a passing interest in rock and roll music. He particularly enjoyed Creedence Clearwater Revival, Fleetwood Mac, and Buddy Holly — he saw productions of “Buddy” in London and on several stages in the United States.

He had also never lost his interest in athletics, and was Fairfield University’s faculty representative to the NCAA.

Charlotte Wakeman, 

The First Superintendent

As of 2019, Ridgefield has had 19 school superintendents. Only three were women, but among those was the very first superintendent: Charlotte Wakeman. After she left in 1921, it was 85 years before Ridgefield hired another woman for the job.

An impressive person who was said to be close to six feet tall, “Biddy” Wakeman was remembered not only as a leader in bringing modern education to Ridgefield, but also as a disciplinarian and one who had a fondness for huge hats.

A native of  Copake, N.Y., Charlotte J. Wakeman was born in 1877 and grew up in Danbury. She came to Ridgefield in 1906 to be principal of and a teacher at the Center School on Bailey Avenue. 

In 1915, Ridgefield’s school system was considerably modernized with the addition of the Benjamin Franklin Grammar School, to which her classes were moved, and the opening of Alexander Hamilton High School at what had been the Center School. A year later, the district modernized even further with the creation of the job of school superintendent to oversee all the teachers and other staff. Wakeman held the position and at the same time continued to serve as a teacher. 

Wakeman was one of a number of Ridgefielders — educators, parents and “summer people” — who were leaders in modernizing the schools and moving the curriculum into the 20th Century. When she arrived here, the town had no high school. After Hamilton High opened, Wakeman then focused efforts on making it better. Even students chipped in: The girls in the home economics class under a Mrs. Myer created a “for a better high school” fund to raise money for the school.  

“I bought three hundred-pound bags of raw peanuts,” Wakeman recalled in 1968 when she was 90 years old. “After school the girls under the supervision of Mrs. Myer shelled those peanuts and salted them. Then they sold them at entertainments in the town hall and took orders for them. When they were finished with that, they gave the money made from sales to the Board of Education ‘for a better high school.’”

The girls also encouraged their mothers “to make cakes for several cake sales. They did many other things and gave the profits to the fund.”

Wakeman was known for keeping her classes orderly. Tabby Carboni, who had her as a teacher in 1912 and 1913, recalled that “she gave me the ruler many times!” Carboni added, however, “I wasn’t bad — there were others who got it a lot more than I did.”

She was also known for her hats. During her career in Ridgefield, Wakeman was photographed several times wearing enormous hats — in one picture, the hat appears four times the width of her head, and nearly twice as high. They were no doubt a style of the day, but she would don them indoors, too, even for group photographs where everyone else was hatless.

After World War I, the town was going through a protracted and sometimes bitter dispute about the modernization of  schools. Leading the support for a conservative approach was school

board Chairman Richard Osborn, owner of the Ridgefield Supply Company. As chairman, “he tangled repeatedly” with  Wakeman, and with Dr. William H. Allee, “her sponsor and supporter,” The Ridgefield Press later reported. (Dr. Allee, covered in a separate Who Was Who profile, was perhaps the most active worker for better education in Ridgefield early in the 20th Century.)

By 1921, Wakeman had had enough fighting and resigned. She took a job teaching English at the high school in Mount Vernon, N.Y., remaining there until her retirement in 1937. 

However, she continued to live in a small house on Main Street for some years,   commuting to Mount Vernon, and maintained contact with her former staff members over the years. In 1937, Ridgefield teachers and friends honored Wakeman on her Mount Vernon retirement, holding a tea for her at the Book Barn on Wilton Road. The attendees included a who’s who of 20th Century Ridgefield educators: Mary Regan, Mary Moylan, Marie Kilcoyne, Mary and Elizabeth Boland, Ruth Wills, Eleanor Burdick, Josephine and Alice Hearst, Margaret and Agnes Carroll, Catherine O’Hearn, Grace White, Isabel O’Shea, Linda Davies, Francis J. Bassett, Charles D. Crouchley, Levio Zandri, and Clifford Holleran.

Although she held no academic degrees, Wakeman had studied at Columbia, Yale, Dartmouth, and New York University. She was also a founder of the American Woman’s Association, a once active suffragist organization. She died in 1969 at the age of 91. 

One of the few Ridgefielders alive by the turn of the 21st Century to remember Biddy Wakeman was Mary Creagh, who recalled her as her school’s principal in 1918. “I remember I thought she was very tall and imposing, like a ship in full sail,” said Miss Creagh. “When I met her years later, she didn’t seem that tall at all.”

Perhaps she had taken off her hat.

Alice V. Rowland: 

Leader on Many Fronts

In an era when women in politics were uncommon, Alice V. Rowland stood out as a leader on many fronts. 

In 1931, she was the second woman elected a state representative from Ridgefield. Twelve years later, she became the first woman state senator from Ridgefield, was elected to three more terms, and, according to The Press, “wielded considerable influence in the Capitol … As a legislator she promoted the development of Sherwood Island State Park, larger state aid grants for schools, and the construction of state-owned technical schools.” 

Around 1950, Mrs. Rowland also became Connecticut’s first woman deputy sheriff, a job she held four years. 

A native of New York City, Alice V. MacSherry was born in 1894. While still a child, both her parents died within a few months of each other, and she was taken in by an aunt who lived in Easton.

In 1910, when she was only 16, she began teaching school in Easton, and education became a lifelong interest. 

She came to Ridgefield with her carpenter husband, Joseph, in the 1920s, immediately became immersed in the civic, political and social life of the community, and remained a major figure in many organizations over more than 40 years. 

She was active in the PTA (there was only one for all the schools), the Grange, the League of Women Voters, Republican Women’s Club, Red Cross, 4-H, American Legion Auxiliary, and many World War II home-front efforts. 

She was also active at St. Mary’s where she was a member of the Rosary Society for 40 years, many as its president, and was active in the National Council of Catholic Women.

In 1943, Gov. Raymond E. Baldwin appointed her to a six-year term on the state Board of Education. She was also a vice president of the Connecticut PTA.

She served a term on the Republican State Central Committee and, in 1954, party leaders asked her to run for secretary of the state; after eight ballots at the convention, she lost to another woman whom party leaders decided had a better chance of winning. 

Mrs. Rowland retired from politics in 1964 and eventually moved to Florida where she died in 1971 at the age of 75. 

Rowland Lane, off East Ridge, was named for her and her husband.

The Shapleys of the School 

Of the many private schools that operated in Ridgefield during the 20th Century, none was quite like the Shapley School. It was a place where wealthy families sent gifted but sometimes undirected children to a estate-like environment that featured tiny classes, sophisticated courses and nightly dinners by candlelight.

Founded by Carl and Virginia Shapley, the sixth-through-12th grade school operated from 1962 until 1967 on the 26-acre grounds of the old Outpost Inn  — now Fox Hill condominiums.

However, its small size and large overhead doomed the operation. And the news that  undercover police found students using drugs did not help efforts to rescue the school.

Carl Betz Shapley was born in 1927 in Cambridge, Mass., a son of the famous Harvard astronomer, Harlow Shapley (who became a member of Shapley School’s board of directors). Carl’s

brother was 2012 Nobel Prize-winning economist Lloyd Shapley. 

Shapley grew up in the intellectual atmosphere of Cambridge where his family’s friends included the likes of Albert Einstein. 

He attended private schools in Cambridge and in Litchfield, Conn., and studied at Harvard and at Principia, a Christian Science college near St. Louis. Considered a gifted musician, he studied in Paris and Vienna before the war for a career as a conductor. However, he wound up after the war working with the National Gallery of Art on identifying and cataloguing rescued works of art that had been stolen by the Nazis. 

After more studies in Europe, including at the Louvre, he turned to teaching, and was an instructor at private schools in Connecticut before establishing The Shapley School with help of wife, Virginia Thayer Shapley, who had been a big-band singer in the 1940s. Mrs. Shapley’s grandmother was one of the founders of Sweet Briar College in Virginia and her mother was the very first student there.

The Shapleys began operating a school in 1962 in New Canaan, where their administrative

offices were. In 1963 they leased and soon purchased the recently closed Outpost Inn on Danbury Road in Ridgefield to establish their campus.

It was no ordinary private school. Shapley featured:

• A student to teacher ratio of 4 to 1.
  
• Availability of instruction in Greek, Latin, French, Chinese, Italian, Russian, Spanish, and German from seventh grade on.
  
• Courses in space biology,  Greek philosophy and drama, geology, Far Eastern history, classical ballet, play production, piano composition, and many other subjects ordinarily found at college level. Students also took Bible classes.
  
• Dinner each night by candlelight in what was once the dining room of an inn where celebrities like Eleanor Roosevelt were served.
  
• A manor in England, ski lodge in Vermont, and a campus in Florence where students could spend vacations or summers in special learning and/or recreation programs. Shapley field trips included two weeks in Greece.
  

 “A 12-year-old can think real thoughts and the point is to create an atmosphere in which he

will produce,” Shapley said in a 1965 interview with the Ridgefield Press. 

He told the Danbury News-Times: “The talent is here in America, but it is wasted and neglected in the mass majority system of education.”

Shapley felt that teaching the Bible along with the many academic and arts-related courses would help establish a “nonsectarian self-discovery of those qualities and principles of respect and love underlying a constructive and dynamic environment.”

A  promotional brochure included among school’s many objectives: 

• “To establish in the hearts and minds of the young people of today a recognition and appreciation of the basic values inherent in a liberal education;
  
• “to re-establish the primacy of deep spiritual thinking;
  
• “to bring fresh insight into new realms for discovery;
  
• “to establish throughout the world a concept of education based upon the acknowledgement of man’s spiritual heritage and unlimited perfectibility.”
  

With a total enrollment that never exceeded 52 students spread over six grades, Shapley School had to charge a relatively high $3,000-a-year tuition — equivalent to about $27,000 today. By 1966, the school was struggling to pay not only its staff of 15 people, but its mortgage.

The school also had to deal with a serious public relations blow. On Dec. 5, 1966, while Carl Shapley was conducting a Bible class, 15 policemen descended on the campus in a drug raid, and wound up arresting two 17-year-old juniors for possessing marijuana and alleged amphetamines. The raid, which made headlines in many newspapers, was the result of an undercover investigation in which at least one especially youthful-looking police officer was posing as a student.

Rumors of the school’s possible closing worried students. “There is nowhere else I can go after this,” one student told a reporter. “This was my last chance to...to...I guess, make it.”

Desperate efforts were underway in the spring of 1967 to save the school — Shapley promised it would open in September. But despite an April fundraising art show and sale that featured works by Picasso, Utrillo and Chagall, the school continued to fall behind in its mortgage payments. A court approved a foreclosure sale at which the high bidder was David Paul, who went on to build Fox Hill condos. Paul, who was building Casagmo at the time, offered $146,500 ($1,093,000 today), far less than the $200,000 ($1.5 million) Shapley said the property was worth.

After the Ridgefield campus closed, the Shapley Schools International maintained a school in Florence for eight years.

The Shapleys then taught and traveled extensively, including in the United Kingdom, India, Greece, and Russia. Carl Shapley promoted the New World Educational Foundation, which he helped found, and was also a fellow of Royal Society of Arts in England.

 In 2005, Virginia Shapley moved to Ridgefield where, in her 80s, she became involved in the community.

“Even at 85, she was amazingly energetic, taking an active role in her new ‘hometown’ — from participating in peace walks to being an administrative assistant for life-enhancing techniques presentations to members of Founders Hall,” said her daughter, Judith Watkins of Hamilton, Mont. 

“She and Carl have had an exciting, exotic life since Ridgefield days and it was a bit ironic

for her to move back there and even to tour the condo development on the grounds of the old school, pointing out to me the preserved features from ‘the old days.’” 

Virginia Shapley died in 2007.

Carl Shapley continued his travels and humanitarian activities. He was a “peace ambassador” in the Universal Peace Federation, based in England, which said at his death, “He has been a longtime supporter of UPF and preceding organisations with the uncanny ability of turning up in the UK at the right  times to support our major activities.”

Late in life he considered himself an ontologist, one who studies the “branch of metaphysics concerned with the nature and relations of being.”

In 2012 he died at age 84 in Chisinau, Moldova, part of the former Soviet Union, where he is buried.

When the infamous drug raid occurred in 1966, most Shapley students were saddened at the harm it did to their school’s reputation. Several suggested that marijuana use was “more prevalent at the more placid-seeming Ridgefield High School,” one New York City newspaper reported.

A 17-year-old — who had earlier attended the National Cathedral School with President Lyndon Johnson’s daughter, Luci — observed: “Shapley is a trip in itself. You don’t need drugs.”

Robert W. McGlynn: 

Beloved Man

Many of us often forget the impact that teachers have had on us. Pulitzer Prize-winning writer John McPhee never forgot a Ridgefield native who had a major influence on his life.

    Robert William McGlynn was born in 1921 into a working class family who lived on Fairview Avenue. His father, J. Edward McGlynn, was a house painter who late in life became an acting postmaster of Ridgefield.

    McGlynn attended Ridgefield schools and excelled at Ridgefield High School. In his senior year he was editor of The Hilltop Dispatch, the school newspaper, which that year won high praise in the Columbia University scholastic press competition. He was ranked second in his class of 37 students  (behind Stata Norton, who went on to become an acclaimed professor of pharmacology and dean of the University of Kansas School of Health Professions).

    As #2 in his class, McGlynn became salutatorian at the 1939 graduation. His speech, called “Through the Rough,” likened life to a game of golf, in which a group of men play the 18th hole. One player gets a hole in one while others, running into obstacles with their shots, struggle to

reach the cup. The strugglers are gaining more from the game — or from life, he suggests. “It is always wisest and best to seek that goal by the more difficult pass, for with the dumps and the knocks come the care and experience demanded by the importance of the position to be attained,” he says. “Those same bumps and knocks mold the character of the individual and the more intricately molded the character, the more capable the individual.”

One sentence in his talk, describing stronger vs. weaker players, perhaps hinted at one of his own struggles: “Determination, education and competency are ready and willing to back up the weaker.” In his senior year, his physician told McGlynn his health was too fragile for him to attend college and that he might not live beyond the age of 21.

McGlynn ignored the doctor’s advice and went to Wesleyan University where, in 1942, he was chosen a member of Wesleyan’s Honors College. Early on in his college years, he had planned to become a psychologist, “an outgrowth of my profound interest in human nature and all its intricacies,” he once told Karl Nash, editor of The Ridgefield Press.

However, McGlynn apparently found literature more rewarding than psychology. After he graduated in 1943 he was immediately hired as an English instructor at Deerfield Academy in Massachusetts, where he eventually became a legend.

At Deerfield, around 1948, McGlynn met a new student named John McPhee, who had transferred for a post-graduate senior year after completing Princeton High School and before entering Princeton University. Though McPhee never actually had him as a classroom teacher, McGlynn became both a mentor and a lifelong friend. 

In a 1996 essay McPhee recalled one of his first encounters with McGlynn — on a football practice field.

 “Attendance was taken exactly 17 times a day,” McPhee wrote, remarking on how closely

Deerfield students were watched. “In fall, attendance was taken on the Lower Level by Robert McGlynn with a clipboard. Relying on recognition alone, he checked off names. In the ranks and files of lightweight football calisthenics, he failed to see me. He walked around behind my jumping and flapping teammates, and found me lying on the ground looking at the sky. He liked that. He checked me off. In the extended indolence on the grass, he recognized essence of writer.”

    McPhee biographer Norman Sims describes McGlynn as “a voracious reader with an Irish background and a babbling, fluid way of talking.” He got McPhee excited about literature in a way his classroom teachers never had. One day he’d hand McPhee a book and later McPhee would go back and discuss it with him. “He was willing to talk about them, that was the thing,” McPhee said. “Like the students, he lived there the whole time and the school was his life.” 

And talk he did. McGlynn was famous for his amazing outpourings. As McPhee put it in 1984, his words “come in cloudbursts, in flooded rivers, braided cataracts, foaming white cascades. Kick him in the leg and words pour out his ears.”

In the foreword to McGlynn’s only novel, Ten Trial Street, McPhee wrote that McGlynn “became, among other things, a student of his students, exposing their innards with rays of humor that went to the bone but cut nothing. He led us up the hill to Joyce and Conrad, and down the other side to meet ourselves. He was prodigal with his talent — that brook he was babbling wherever he might be. It was for anyone. It was for me. As a writer now, I am forever grateful to him. And, as it happens, I was never in his class.”

McPhee biographer Michael Pearson put it simply: “McGlynn sparked in McPhee a deeper love of reading than he had ever experienced.”

During his years at Deerfield, McGlynn became widely known for inspiring many young writers and teachers, and for his interest in the literature of Ireland, birthplace of his grandmother and his great-great grandfather. He brought several Irish poets to the campus to speak and work with with students — one, Peter Fallon, spent a year at Deerfield. These visits helped spark McGlynn’s interest in publishing the works of Fallon and others by creating the Deerfield Press, a publishing house

described in its day as “important in the worlds of letters and small presses.”

In 1984, the year he retired, Deerfield Press published the small book, The Little Brown House: A Garland for Robert McGlynn. Among its contributors were poets Seamus Heaney and Robert Creeley. And, of course, John McPhee.

Three years later, alumni and friends donated $850,000 toward establishing the Robert W. McGlynn Chair in the Humanities at Deerfield Academy.

After his retirement Bob McGlynn moved to a log cabin in Warrenton, Va. He read  four to five books a week, gave readings of Irish poetry in the area and maintained a sizable correspondence with former students around the world. (More than two dozen of those students became school, college or university English teachers.)

McGlynn also eschewed technology of almost any kind. “I know nothing of faxes, word processors and computers,” he told a friend around 1990. “I don’t even own a telephone.”

He was only 72 when he died in 1993 — but he was long past 21. His ashes are buried in St. Mary’s Cemetery. 

Among the new friends he made in Virginia was newspaper publisher Arthur Arundel, who greatly admired the retired teacher. “There are so few like McGlynn who so completely earn and define the appellation of ‘Beloved Man,’” Arundel wrote after McGlynn’s death.  

George B. Leeman Sr.: 

Music for Kids and Stars

When George B. Leeman was only two years old, he astonished family members by picking out tunes on a piano. “By the time his fourth birthday rolled around,” The Ridgefield Press reported in 1962, “he was ready for a recital.” 

Born in 1907, the Oklahoma native studied music at the University of Oklahoma and went from there to RKO studios in Hollywood where he worked on RKO’s “Hollywood on the Air” radio show. 

However, he soon wound up in New York, working CBS radio and later television as a composer and arranger for the likes of Frank Sinatra, Perry Como, Dick Haymes, Paul Whiteman, Andre Kostelanetz, Archie Bleyer, and, for 12 years, with Arthur Godfrey. 

For Godfrey, Leeman prepared music for the daily show, as well as Godfrey’s weekly Talent Scout program. He served on the audition committee for the latter, and was involved in the auditions of many future stars, including Eddie Fisher, Wally Cox, and the McGuire Sisters.

A Ridgefielder since 1942, Leeman was instrumental in the founding of the Ridgefield Symphonette in 1964, and aided its growth into the Ridgefield Symphony Orchestra, one of the top small orchestras in the country. (His son, George Jr., has also been a leader in the orchestra, and wrote the program notes for many years.)  When it gave its first concert in April 1965, the symphonette consisted of 24 musicians, 13 of them residents and only seven of them professionals.

“The reason for our existence is to provide the best possible entertainment for the people of Ridgefield who enjoy music of this calibre,” Leeman said in a 1972 letter to The Press.

After his retirement from CBS in 1959, Leeman gave private piano lessons to Ridgefield youngsters.  He also composed and arranged many songs and musical programs that were performed by children in the Ridgefield elementary schools, where his wife, Evelyn, taught for many years.

“Music,” he said, “is a therapy. Most children find something in music that relaxes them.” 

Leeman died in 1978 at the age of 70. Two weeks after his death, the Board of Education named the auditorium at Scotland School “the Leeman Room” in his honor.

Clifford A. Holleran:
Beloved Principal

For 36 years,  Kip Holleran was principal of Ridgefield High School and over all that time, he could knew each and every student by name. 

“Whenever a graduate would return to the halls of his secondary school learning, he or she would first stop at Mr. Holleran’s office, not because he had to, but  because he wanted to,” The Ridgefield Press said in an editorial about the principal. 

Born in 1895,  Clifford Ambrose Holleran grew up in Watertown, Conn., and graduated from Bucknell in 1920. A year later, he was hired as both a principal and a teacher at Hamilton High School, the original Ridgefield High School, then located on Bailey Avenue. 

The late Dick Venus, town historian, told this story of Holleran’s first day in a classroom in Ridgefield: 

“He wanted the names of each of his pupils. He asked that each one arise and give his or her last name as they were called on. 

“My brother Joe sat in one of the front seats and when Mr. Holleran pointed to him, Joe dutifully arose and said his name was Venus. The new principal blinked at the rather unusual name and then called on the next student, who declared his name was Romeo (probably Fred Romeo). 

“With that, Mr. Holleran called a halt to the proceedings as he had a feeling that he was being taken advantage of. In a loud voice, he said, ‘Some of you think you are pretty smart but if the next one who gets up tells me his name is Juliet, there will be trouble.’ 

“When the two boys were able to prove that their names were actually Venus and Romeo, Mr. Holleran had a big laugh over it.”

In his early years, he spent more time teaching than principaling — he taught geometry, trigonometry, science, chemistry, physics, and mechanical drawing. 

When he arrived at the school, there were no organized athletic teams, and he created baseball and basketball squads. For 20 years, he coached both, transporting them to out-of-town games, running magazine drives to pay for them, and sometimes winning championships.

Occasionally he’d even referee the games — because of his reputation for fairness, opposing teams didn't mind. 

After World War II, when the school grew large enough to hire an athletic director to take over, football was finally added and Holleran became a full-time principal — and twice was acting superintendent of schools.

“Mr. Holleran [was] a very kindly man,”  Elsa Hartmann, longtime teacher of history and German at RHS, recalled in 1983. “Even so, he was a strict disciplinarian and woe betide any student who got out of line. 

“On one occasion he heard a noise in the hallway and opened the door to see what was going on. Jim Sullivan had been sent to a window at the rear of the hall to clap the chalk dust out of some blackboard erasers. Lawrence Brundage opened a door at the other  end of the hallway and Jim promptly threw an eraser at him. Of course, the eraser was returned with gusto and soon the air was flying erasers. 

“As the door between the two combatants opened, a balding head appeared and caught the full force of an airborne eraser. When Jim saw what he had done, he clambered out the window and ran as fast as his legs could carry him.”

Holleran retired in 1957, but like many educators of the first half of the 20th Century, he lived here, was active in the non-school community, and remained so in retirement. 

He was a founder and the first president of the Rotary Club, served on the Ration Board during the war, and was a director of the Boys Club for 14 years. He loved golf, and his favorite partner was Tabby Carboni. 

In 1947, he married his longtime sweetheart, Grace C. White, after her retirement following 44 years of teaching here. She died in 1963 at the age of 79, he in 1971, age 78. 

Sereno Jacob:
Fighter Pilot, Playhouse Fighter

A pilot who won the Croix de Guerre for shooting down German fighters in World War I and who was among the earliest to fly commercial airliners may have been largely responsible for the venue that is now the Ridgefield Playhouse.

Born in Brooklyn in 1896, Sereno Thorpe Jacob grew up in Westport. He became a carpenter, but soon ran away from home and joined the Merchant Marine.

Early in World War I, he volunteered as an ambulance driver for the American Field Service in France. While there he became interested in aviation, trained as a pilot, and wound up joining the Lafayette Flying Corps, a group of American volunteer pilots who flew in the French Air Force before the U.S. entered the war. 

He piloted Nieuport 27 and SPAD S.XIII fighters against the Germans from October 1916 through January 1918. He earned the Croix de Guerre with Palm for exceptional bravery after a battle in which he and another pilot shot down a German observation balloon and were then attacked by five German planes. “The American aviators succeeded in sending two of the German planes to earth and drove off the three others,” said a contemporary account.

A record of his service in France reported that “most pilots are glad of an occasional rest from flying, but Jacob, according to his comrades, was always ‘gonfle’ [“pumped up”] — three patrols a day were nothing out of the ordinary for him. The habits of the local Boches [Germans] formed a study of never-failing interest; it was his delight to lie in wait for the wary Rumpler [a German plane] which so often made its photographic reconnaissance at noon, heralded by tracery of white shrapnel puffs across the sky. Though he has three official victories to his credit, Jacob had had bad luck in getting confirmation, and among the chalky hills of the Champagne, ... there are without doubt several fast-disappearing heaps of wreckage which are rightfully his.”

Jacob later served briefly in the U.S. Army at the end of the war..

When the conflict was over, Jacob worked for a while for an American automobile company selling Cadillacs in Belgium, but returned to the states in 1921, when he married Marion Couch Wakeman of Westport. Soon after, the couple moved to Ridgefield to a house on the corner of High Ridge and Barry Avenue (behind the big stone wall built by Joe Knoche) that had belonged to Jacob’s grandfather, Sereno Allen. Their arrival was almost legendary. 

“My father’s greatest public relations coup was arriving in Ridgefield with his beautiful bride, wearing two raccoon coats, in a Stutz Bearcat,” son Merritt Jacob said.  “People were always ready to tell me about their ride in the Stutz — which had an exhaust cutout so that the roar of the engine could be heard miles off.”

For a brief period Jacob flew Ford Trimotors for a regional airline providing service to such cities as Bridgeport, Newark, N.J., Albany, N.Y., and Springfield, Mass., but he left around 1930 when the airline lost its mail contract and went belly-up. Capt. Eddie Rickenbacker, a World War I flying ace who founded Eastern Airlines in 1926, knew him, hired him and Jacob flew Eastern’s Curtiss Condor airliners for seven years.

“He was a very early member of the airline pilots union and wrote a paper defending the union, which did not please Captain Eddie,” said Merritt Jacob. “And so they parted ways.”

Jacob’s new career was very land-based: real estate. He worked with Harold E. Finch, a prominent oldtimer and owner of what became Squash’s New Store and is now Ridgefield Office Supply.  However, though he wasn’t flying, he often spoke to clubs and organizations about his years as a pilot, both in World War I and with the airlines. The challenges were many and the instruments few. “Flying blind is like walking a tightrope in a dark closet blindfolded,” he told a First Congregational Church club in 1938 about piloting a plane in overcast weather.

Jacob served three years as chairman of the Board of Assessors and, according to The Press, “devoted his talents to putting that office on a more business-like basis.”

He also served on the building committee that expanded the “old high school” on East Ridge in the late 1930s. Merritt Jacob reports that, “according to my mother, he fought very hard for a separate gym and auditorium — which put Ridgefield way ahead of any of the neighboring towns facilitywise and gave us the auditorium that is still in use” — the Ridgefield Playhouse. “I myself got to see Toscanini conduct in that auditorium. My father could be very forward-looking.”  

During World War II, Jacob was chairman of the Ridgefield Defense Council and worked to bring about greater public appreciation of the danger of the war reaching this country. He was not always successful. In March 1942, he asked the town for $25,000 for civilian defense projects; the Town Meeting later authorized $2,500. 

He was a member of the Republican Town Committee, the Lions Club, and the American Legion. He also belonged to the Last Man’s Club, a group of World War I veterans who met annually to remember their comrades  until the last man died. When Jacob died in 1947 at the age of 51, he was only the second of 31 members to pass away. 

Sereno Jacob loved traveling not only on land and in the air, but also on the sea. He was an expert yachtsman, and had owned 40 and 50 foot sailing vessels that took part in many major racing events. But he also loved a good ride in that Stutz.

One day he was parked in front of town hall when Joe Zwierlein happened by. (A local house painter, Zwierlein was well-known in town; he was a volunteer fireman for 60 years and dog warden for 30.)

“My father asked Joe if he wanted to go for a ride,” Merritt Jacob said. “Well, Joe jumped at the chance. After about 30 minutes of driving, Joe asked my father where they were headed, and my father said, ‘Montreal.’”

It took Zwierlein a bit of time to recover from the shock and figure out what he would tell his wife. 

Dr. William Allee:
‘Father’ of Ridgefield High

Few individuals have affected the quality of Ridgefield schools a century ago as much as William Hanford Allee, a name all but forgotten today, but renowned and respected early in the 20th Century. 

“Dr. Allee may properly be called the father of Ridgefield High School,” The Ridgefield Press said at his death in April 1927. “He saw the need of such an institution in town. Although he met with strong opposition, he well knew the justice of the cause. Patiently he worked and finally triumphed.” 

A native of Brooklyn, N.Y., Dr. Allee was born in 1872, graduated from Brooklyn Polytech and Columbia Medical School, and opened a practice in Wilton around 1905. He and his wife, Laura Curie Allee, came to town in 1906, buying the former Hurlbutt place still standing at Main and Market Streets. 

Dr. Allee was elected to the school board in 1912, serving many years. “He was the guiding hand that created and developed the Hamilton High School (Ridgefield High’s original name) and saw it gradually advance into one of the best small town high schools in the state,” The Press said.

He also led the effort to secure land on East Ridge for a new grammar school and ball field – the Benjamin Franklin Grammar School later became Ridgefield High School. 

He was a true activist for education. 

“When we came to Ridgefield, the town did not provide free textbooks for school children,” his wife, later Laura Curie Allee Shields, wrote in her autobiography, “Memories.” “One day, one of his patients, a poor widow with five or six children, came to see him to ask if something could be done about free books, as it was simply impossible for her to buy books for all her children, either new or second hand. 

“Doctor went to see our town attorney, Judge Light, who, by the way, was a good suffragist, and he told him that Connecticut had two suffrage laws giving votes to women, one on all school questions and the other on libraries.” (This was eight years before the 19th Amendment was ratified.)

Allee decided to employ the little-used right of women to vote on school issues, but also learned that the previous time it was exercised, Ridgefield town officials had “lost” a voting list that contained names of women who officially wanted to be able to vote.

“Dr. Allee spoke before our Equal Franchise League and agitated the question with every woman with whom  he came in contact. Two hundred and six women gave their names to him to be made voters. Doctor made the list in duplicate.” The list was submitted to the town’s registrars of voters and they accepted it.

“The day came for the registrars to meet, and the women went to the town hall to be made voters. Doctor was there, and I will never forget the amazement and confusion of the men that so many women came up to the scratch. The men fumbled around at their desks and whispered and conferred with each other, and finally we were told that the list had been mislaid. 

“Doctor was all ready for them and handed in the duplicate list.” Because the original of the list had been properly received and acknowledged, they were forced to accept the copy.

“Cheers went up. The room was full, as well as the hall outside.  Well, we were all ‘made’ and I assure you it was a sacred rite.” 

A  town meeting Oct. 10, 1912, included, down on the bottom of the agenda, the question of free text books. The meeting began at 3:30 in a packed, standing-room-only town hall — about half of the attendees were women. However, most of those women had family obligations and “the men arranged it that the school business came up last. At 5 o’clock we were still there. Many mothers felt they ought to go home, but didn’t. It was almost 6 before the school business was reached. 

“Dr. Allee moved that the vote be taken by roll call, which was passed. Some women whose names were down toward the end of the list, went home and came back; some whose names came first, voted and then left to take care of the homes of those down at the end of the list. 

“Of course we won. I think if we had ever needed any more convincing arguments for woman suffrage, we had them that day.” 

“Memories” also describes how Dr. Allee went around, drumming up money to buy the East Ridge land for the new grammar school, part of the package that included creating Hamilton High School. Education advocates had agreed to buy the property to help convince the voters to build the town’s first modern school. 

Allee approached book publisher E.P. Dutton of High Ridge for a contribution, explaining the need for a modern school in Ridgefield. 

“Mr. Dutton was most enthusiastic and sympathetic, and he turned to Doctor and said, ‘Suppose we take it to the Lord.’ Doctor told me he knelt down by the couch and made a most beautiful prayer for direction and wisdom. Rising from his knees, he went to his desk and made out a check for $1,000 and, giving it to Doctor, told him, ‘Here, my boy, go to it!” ($1,000 then was worth nearly $25,000 in today’s dollars.) 

“Dr. Allee never rested, but day after day he went to see people from house to house until he had the whole $16,000” needed for the land. The town approved the schools project and both the grammar school and high school opened in 1915. And it was Dr. Allee who suggested the names for both; Hamilton and Franklin were two of his heroes from history.

Though a physician, Allee helped establish and was first president of the Fairfield County Farm Bureau. He was an official of the local, regional and state organizations of the Congregational Church, and his special interest was in youth groups. 

“His love of justice and fair play led him to champion many causes of importance in church and community,” The Press said.

Dr. Allee was 55 when he died in 1927.