Dec. 16, 2025, 8:00 a.m. ET
Tootie McGregor Terry was a beloved philanthropist in early 20th-century Fort Myers.She fulfilled her first husband’s vision by turning a cow pasture into the Fort Myers Yacht and Country Club.The club, which featured Fort Myers’ first golf course, opened in 1908 but ultimately failed by 1914.Despite its failure, her contributions are considered foundational to the city’s development.
She lived in two worlds, had three different names and treasured four great loves.
To those in Cleveland, she was known as Jerusha Barber, the daughter of a middle-class judge. In Fort Myers, she was Tootie. A hearty gal, Tootie McGregor or Tootie McGregor Terry was a beloved philanthropist who seemed as comfortable with a rod and reel as she was in a full-length skirt.
She married two of the more accomplished men in the country – Ambrose McGregor and Marshall Terry – before and into the 20th century. Those Southwest Florida pioneers helped form Fort Myers into much of what it’s known by today.
One of Tootie McGregor Terry’s endeavors was turning a cow pasture into the Fort Myers Yacht and Country Club over 100 years ago.
Although short-lived, it can be said it was Fort Myers’ first golf course. The enterprise failed miserably but the residual effects resonate today.
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“I think the only woman of her equal is Mina Edison,” said artist Don Wilkins, who created a bust of Tootie McGregor in 1990. “Of the early contributors, I think she’s the most under-celebrated of them all.”
“She was the woman who made the largest contribution to Fort Myers,” author Tom Hall said. With Robin Tuthill, he co-wrote “Female Pioneers of Fort Myers: Women Who Made a Difference in the City’s Development.”
Before professional and college baseball, before local fairs, before horse racing, before the 4-H Club, Terry Park on Palm Beach Boulevard was known for something else — golf.
Tootie McGregor seemed interested in carrying on her husband’s legacy whenever possible. Golf was no exception.
Ambrose McGregor, who invested in citrus, 32 residential and commercial parcels, and bankrolled the first brick building in town, suggested they build a golf course in 1897, according to Tuthill and Hall’s book. He then donated an acre of land in east Fort Myers as the site for a country club.
“Ambrose McGregor was one of the 10 richest men in the country,” said Maryann Dominiak, who has researched the beginnings of golf in Fort Myers. “Rockefeller encouraged him to take compensation in the form of company stock.”
McGregor didn’t see his golf vision come to fruition. After battling cancer, he died on Oct. 29, 1900, at age 58.
At the time of his death, his worth would’ve been more than $12 billion today, according to measuringworth.com.
Jared Beck, acting chairman of the City of Fort Myers Public Art Committee, added, “She could’ve gone anywhere but chose to stay here. These people saw that this could be a fantastic little town.”
Dr. Marshall Terry entered Tootie McGregor’s life just at the right time.
They were both alone. He never married. She lost her husband and son within two years.
They tied the knot on Dec. 12, 1905. She was 62. He was 57.
Wanting to fulfill Ambrose’s wishes, the two worked with other residents to complete plans of turning that cow pasture into the Fort Myers Yacht and Country Club on April 26, 1906.
Tootie McGregor Terry and Marshall Terry had grandiose plans for the country club. They built a $2,500 clubhouse that included a fireplace, sky blue French doors and locker rooms with shower baths, an unusual feature in those times, according to a commemorative magazine on Terry Park in 2006. They also wanted tennis courts, a yacht landing, basketball court, croquet courts, gun traps, a baseball diamond and a grandstand seating 500 on site as well as a golf course.
Opening Day was Feb. 21, 1908.
The clubhouse was partly finished. Weather was cold and cloudy. Players tried playing on the crude, nine-hole course with little success, according to historians.
By opening day, the club was $2,000 in debt. Membership soon dwindled. World War I began in Europe in 1914.
That same year, the Fort Myers Yacht and Country Club went out of business.
Note: This is an edited excerpt from a June 4, 2016, article in the News-Press headlined “A story of loves, golf and Fort Myers history” by Craig Handel.
