Tracing the gillespie fortune from pennies to a $100m gift – stamfordadvocate

But in Stamford, a trail that starts in 1878 with pennies paid for Advocate newspapers produced by William Gillespie has led to a $100 million trust — most of which will be streamed into medical advancements at Stamford Hospital, scholarships through the local Rotary Club and programs for families overseen by the city’s First Presbyterian Church.

As Stamford launches a yearlong celebration of its 375th anniversary this week, the saga of the Gillespie dynasty reveals how the family expanded the city’s oldest existing business and helped shape the city itself. Their influence takes abrupt turns through the decades like information whizzing through pneumatic tubes at former Advocate offices.

Gillespie newspaper family leaves $70 million to Stamford nonprofits

Kingsley Gillespie, who created the trust with proceeds from the sale of The Advocate and Greenwich Time in 1977, was a one-man version of “It’s a Wonderful Life,” with the gruffness of Mr. Potter and the generosity of George Bailey. Former employees describe him as “exacting,” “a myth,” a “hard-working Yankee” and “grumpy.”

Newsboys collected a nickel for an Advocate paper when Gillespie was appointed as publisher on Jan. 1, 1942, a figure that quadrupled to 20 cents by 1977, when the family sold the business. Gillespie’s son, Kenyon, transformed his share of all that loose change into an $80 million contribution to the trust set up by his father. To those revealed last week as the recipients of Kenyon’s largesse, he was a stranger they could only characterize as a frugal recluse. Friends say that was not the case; that he was merely a private man who was “brilliant” at investing. Even as he coped with Macular Degeneration and Parkinson’s disease before his death last March, Kenyon listened to financial reports on Bloomberg Radio while walking in the sand on the other side of Long Island Sound.

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The Gillespie dynasty

1860: Journeyman printer William Gillespie responds to a job posting in the Stamford Advocate.

March 20, 1868: Gillespie takes sole ownership of paper a year after buying it with a partner.

Aug. 15, 1895: Kingsley Gillespie is born on Shippan Point.

1913: Gillespie graduates from Stamford High School as class valedictorian.

Jan. 1, 1942: Kingsley, 46, is announced as editor-in-chief and publisher of the Stamford Advocate following deaths of two brothers in the same year. He soon drops the editor title.

1942: A sailing enthusiast, Gillespie helps organize the Stamford Harbor Patrol to teach residents navigation, before entering military service. His wife, Doris, volunteers as a Red Cross Motor Corps driver. Doris is also a founder of the Stamford and Shippan Garden Clubs and an organizer of the creation of Stamford Museum.

1947: Gillespie is elected “an incorporator” of Stamford Hospital, where he was actively involved for more than 34 years, as vice president for eight years and through advisory work on the building, future planning and executive committees.

Dec. 29, 1977: Kingsley leaves his office for last time after selling both papers to Times Mirror for $20 million in stock. The 117-year family association with the paper ends.

March 23, 2015: Kingsley’s son, Kenyon, dies, triggering release of funds from the $100 million Gillespie Charitable Trust.

March 30, 2016: Officials announce the trust will be divided six ways, with half intended for Stamford Hospital and 10-percent cuts to Stamford’s Rotary Club and First Presbyterian Church.

A modest start

The family’s origins in Connecticut began in 1860, when Kingsley’s uncle, William Gillespie, arrived from Canada and joined the Stamford Advocate staff as a “printer’s devil” at age 21. Eight years later, he bought the paper.

The money came slowly from each sale of the weekly paper, which cost $2.50 for an annual subscription. Kingsley’s father, Richard, took a gamble in 1892 by turning the Advocate into a daily — despite public skepticism that Stamford wasn’t large enough to support it.

During the Great Depression, the Gillespies maintained cash flow by allowing advertisers to delay payment. Profits eventually poured in with the additional printing of everything from high school yearbooks to checks.

After becoming publisher in 1942, Kingsley tried to fend off the threat of radio news by posting hourly updates on a roller printer in the window of the Neo-Italian Renaissance style office at 258 Atlantic St. He soon eliminated the competition by buying the station that became WSTC. Over his career, he maintained a modern newspaper by investing in press upgrades and replacing typewriters with computer terminals the size of TV sets.

A path not chosen

As a young man, Kingsley seemed destined to play no more of role in the paper than his son would. After earning 121/2 cents an hour feeding the flatbed press as a high schooler in 1912, he got a degree in chemical engineering from Massachusetts Institute of Technology and served in the U. S. Army’s Chemical Warfare Service. During World War I, he tested nitro starch as an explosive in grenades in a New Jersey lab and toiled in a mustard gas plant in Baltimore.

As a second lieutenant in 1918, he went to the U. S. Capitol, where President Woodrow Wilson was to announce the end of the war. Lacking a pass to the ceremony, Kingsley climbed in uniform though a basement window, snuck upstairs and found himself in the gallery of the House of Representatives in time to hear Wilson’s historic speech.

Kingsley soon began working for the family’s Stamford Rubber Supply Co., where he rose to president. He became Advocate publisher at age 46 after two brothers died within the same year. For decades, he leaned on an anecdote about studying rubber molecules for 23 years, then getting yelled at by a reader 24 minutes after his first editorial hit the streets. Shortly before his death, he called it a “corny answer,” but maintained newspapers were far more exciting than molecules.

Public service

Kingsley helped form the Rotary Club of Stamford in 1923. As publisher, though, he was drawn to civic duties that filtered throughout the city: as a director at Stamford Hospital, the Chamber of Commerce, Stamford Savings Bank, Ferguson Library, the Connecticut Power Company, and other organizations.

“My cue as a publisher was to be vice president of everything and president of nothing,” he said.

As far as U. S. presidents were concerned, Kingsley maintained a Gillespie tradition of never endorsing a Democrat.

Father and son

Kingsley and Kenyon shared some personal traits. If Kingsley loomed large in his hometown, he also cherished his privacy.

“You were not going to find him out at parties,” said Robert McCullough, 87, former general manager of WSTC and Greenwich Time, which the family bought in 1957.

By the end of his career, Gillespie was “almost a legend,” who seldom appeared in the newsroom but was recognized as “all-powerful,” said Arthur Helms, who was Advocate city editor at the time.

Still, staff members learned he could be paternal, Helms recalled. He would lend money to help employees buy a car, and let them pay it back through payroll deductions.

“You were sort of afraid of him, but little by little the human side would eke out. You’d be shopping at Caldor and spot Kingsley going through the discount shoes,” Helms said.

After long work days in Stamford, Kingsley traveled to Long Island on weekends, often by boat. Kenyon preferred life across the Sound.

McCullough eventually got his real estate license and handled the sale of the Gillespie home in Shippan, where Kenyon once let him live in for several months. Proceeds went to cancer research at Cold Spring Harbor Laboratory in New York.

The payoff

After selling the newspapers, Kingsley maintained an office at WSTC, where “twice a month for a whole day, he would come in and do nothing but sit and open dividend checks,” recalled Dennis Tidrick, who worked for Gillespie at the station and The Advocate, and also lived in the empty house for a year in the 1980s.

Tidrick, manager of technology for Hearst Connecticut Media (which publishes The Advocate and Greenwich Time), said Kenyon was always focused on his portfolio.

Ward Cleary, 72, a partner at Curtis, Brinckerhoff and Barrett in Stamford, represented the estates of Kingsley and Kenyon. He said Kenyon, who earned an MBA degree at Harvard University, made “tremendous investments in the 1990s.”

Kenyon made his own investment decisions and subscribed to paper stock charts because he was not tech savvy, said Robert Vestigo, a friend of Kenyon’s for 30 years. Vestigo said he routinely picked Kenyon up at his Setauket home, and they listened to Bloomberg News reports on the radio while sipping coffee at the beach.

“There was no shroud of mystery around him; he was just private,” said Vestigo, who dismissed characterizations of Kenyon as reclusive. “He just happened to be brilliant.”

Next stop on the money trail

The Advocate editorial that appeared after Kingsley’s death in 1984 noted despite his family’s 117-year role with paper, he was never nostalgic.

“He was convinced that the new Stamford was better than the old, and he had entire confidence in its future,” the editorial reads.

Kingsley invested in that future by establishing the trust, but Kenyon ensured Stamford will yield the dividends for untold future anniversaries — all because he followed the money.

John. breunig@scni. com; twitter. com/john. breunig.