McGregor the boulevard, not the notorious fighter, packs a punch in Fort Myers history

Note to readers: This story was originally published on news-press.com on Nov. 7, 2015. and written by freelance reporter Cynthia A. Williams. We are resurfacing the story today in honor of tonight's fight between Conor McGregor and Floyd Mayweather in Las Vegas. McGregor Boulevard (no relation to Conor) in Fort Myers is one of the most historical roads in the region and this story tells you everything from who the boulevard is named after to how it has transformed in the last century.

The winding history of McGregor Boulevard

McGregor Boulevard is 100 years old this year (2015). When it was completed in 1915, it was the only hard-surfaced road in Fort Myers. It was only a pebbly macadam road, 50-feet wide, but it allowed the transport of building materials into the undeveloped land south and west from town, thus facilitating the expansion of Fort Myers during the building boom of the 1920s.

We can thank a winter resident from Ohio for this historic road. She was a stout, middle-aged woman who came down here for a fishing vacation with her son and husband and ended up buying a place. The usual scenario. Except that this was 123 years ago.

The couple from Ohio

In 1886, Editor Stout of the Fort Myers Press declared that the streets and sidewalks of Fort Myers were "a disgrace to the town." Fort Myers had, in fact, no real roads and the only sidewalk was the crushed shell that two business owners had laid in front of their store on Front (First) Street. In heavy rains, the shell washed into the street.

Six years later, Mr. and Mrs. Ambrose McGregor and their 24-year-old son, Bradford, made an excursion upriver from Punta Rassa to Fort Myers. The McGregors were on a fishing holiday at the Tarpon House and wished to see the little town on the Caloosahatchee that their host, hotel proprietor George Shultz, had told them was worth a visit.

As a close friend and business advisor to John Rockefeller, Ambrose McGregor was, as they say, "no dummy." He was shrewd enough to recognize instantly the staggering potential of Fort Myers. Perched on the bank of a broad river in one of the most salubrious spots in Florida, its growth promised to be spectacular. Mr. and Mrs. McGregor had been advised to bring their ailing son to a warm climate in winter. For practical reasons, then, as well as for investment opportunity, they prompted decided to make Fort Myers their winter home.

Ezra Gilliland's house next to the Edison's winter lodge on the river was available. Mr. McGregor snatched it up for a mere $4,000— pocket change for one of the largest shareholders in Standard Oil — and the following December, he and his wife and son returned to Fort Myers as winter residents. Astutely, McGregor began buying up huge tracts of land for citrus groves, as well as property in town — 32 properties, to be exact — for a total expenditure of $150,000.

To realize any profit from his investments, McGregor would have to encourage a bit more in the way of civic improvements. For instance, Harvie Heitman's general mercantile was a going concern, but it was not up to standard. McGregor told Mr. Heitman he ought to knock down his wood-framed store and replace it with a fine brick building. One can imagine a certain warmth rising from Mr. Heitman's collar into his face, but before he could utter the first choice words that came to mind, Mr. Standard Oil proposed to finance the project, and Heitman's color receded.

Construction of Heitman's new store, the first brick building in Fort Myers, was completed in 1898.

The indomitable Tootie McGregor

Ambrose McGregor died of cancer in 1900 at the McGregor's summer home on Long Island.

Diagnosed with Bright's (kidney) disease, son Bradford died two years later.

Though widowed and now childless, the indomitable Tootie McGregor returned to Fort Myers. Had she not, the growth of this little town, whose conservative vs. progressive factions were perennially embattled over the issue of public improvements, might have been irreversibly stunted.

Tootie understood that Fort Myers could realize its potential of becoming the leading winter resort in Southwest Florida only by cleaning itself up, trading its guns for golf clubs and building a road out of the 19th century into the 20th.

As the widow of a man worth $16 million and now indisputably one of the wealthiest women in the world, Tootie was also canny enough to know that in order to get any of the above done, she might have to pay for it herself.

Let the games begin

In 1904, either Harvie Heitman went to Mrs. McGregor or Mrs. McGregor summoned Harvie, but the result was the construction of a modern hotel at the corner of First and Hendry streets in Fort Myers. Tootie financed the project with only one provision —that the hotel be named after Bradford.

In 1906, Tootie donated 40 acres of the land out in east Fort Myers for a country club. The Fort Myers Yacht and Country Club opened in 1908, but the proposed golf course was never completed. Because bond issues for roads continued to be defeated, it took club members an hour of wallowing through sand to get out there, so they finally shrugged off the effort.

In 1907, Tootie proposed to the town council the construction of a sea wall, suggesting that they build it 200 feet out from shore and, on the fill, construct a 75-foot-wide waterfront walkway from Billy Bowlegs Creek to Monroe Street. This pedestrian boulevard would transform the sewage stinking, garbage dump of the river's edge into a flowered promenade.

Predictably, the public walkway proposition failed, but the seawall was approved and on April 10, 1908, Tootie swung the mallet to the first piling with a vengeance.

Also in 1907, Tootie bought the grand Royal Palm Hotel. The latest owner of the hotel had not the means to open it, and to save this great resort, Tootie bought it, spent a small fortune on improvements, and re-opened it with a glittering social event.

Tootie triumphs

In February, 1912, Tootie called a meeting of the town council and the county commissioners. The gentlemen convened, perhaps nervously. Tootie's proposal, the construction of a hard-surfaced road from Monroe Street to Whiskey Creek, was met with stunned silence.

Since the turn of the century, every effort to get a bond issue approved for road construction had failed. The only "road" in Fort Myers was still nothing but a narrow strip of graded, crushed shell down the middle of First Street.

Let's imagine, then, that at her proposal, the town councilmen laced their fingers tightly across their vests and that Tootie, with amused eyes, added that if they would build the road to Whiskey Creek, she would take it from Whiskey Creek all the way to Punta Rassa.

Tootie had offered Fort Myers the equivalent today of $200-300 million to build its first real highway. We can imagine this generous woman waiting with a quiet smile as the realization of the enormity of her offer gradually dawned upon the town council.

Her one provision, of course, was that the road be named McGregor Boulevard.

An honorable man

Only six months later, on August 17, Tootie died at her summer home at Mamaroneck-on-the-Hudson in New York. She was not alone when she died. With her was her second husband, Dr. Marshall Orlando Terry.

Tootie and Dr. Terry had married one month to the day of the grand opening of the imposing Bradford Hotel in Fort Myers. Born in Utica, New York, Dr. Terry was an eminent New York physician. Among his many honors, Dr. Terry had been Surgeon-in-Chief of the Utica Homeopathic Hospital, president of the Homeopathic Medical Society of the State of New York, and president of the Association of Military Surgeons of the National Guard.

Dr. Terry was also on the Board of Directors of the A. M. McGregor Home, a residence for elderly ladies in East Cleveland. Dr. Terry and Tootie, together with Tootie's sister Sophia and her husband, James McCrosky, had conceived and incorporated this institution in 1904. Tootie, of course, had financed the project.

Almost certainly, Mrs. McGregor and Dr. Terry had moved in the same social circles in Cleveland and New York long before they married. Probably, they were old friends. (In popular legend, they were "childhood sweet hearts," and although Dr. Terry did attend medical school in Cleveland when Tootie was a young woman, this writer has found no documented evidence to support a youthful romantic involvement between them.)

In any case, when Tootie died, Dr. Terry, an honorable man, buried her with her husband, Ambrose, and their son in East Cleveland's Lake View Cemetery, and four months later, he notified the Fort Myers City Council and the Lee County Board of Commissioners to proceed with the McGregor Boulevard project.

McGregor Boulevard was completed, with bridges and culverts, in 1915. The benefit to Fort Myers of this road cannot be overestimated. Tootie and Dr. Terry had laid the infrastructure for the expansion of Fort Myers, channeling out of its political stagnation a free flow of growth from the Caloosahatchee River to the Gulf of Mexico.

A monument to the woman who is responsible for possibly the greatest civic improvement in the early history of Fort Myers stands today, appropriately, in front of the Fort Myers Country Club on McGregor Boulevard. Commissioned by Dr. Terry in honor of his wife, it is a pink granite palm tree, with bronze palm fronds, weighing 24 tons. The inscription on its base quotes Tootie:

"I only hope the little I have done may be an incentive to others to do more."