Times Observer photo by Josh Cotton/Photo courtesy of the Warren County Historical Society Above, Windsor purchased this plot of land at Oakland Cemetery when his mother died in 1906. In addition to Windsor, his parents and an aunt are the only family members buried there, according to the Waren County Historical Society. At left, a late in life photo of Col. Windsor at what we now know was Soldiers & Sailors Park in downtown Warren.

But he couldn’t escape the aging process that we’re all subject to, and as he moved into his 60s in the 1920s, the pace of his life slowed significantly.

The Warren County Historical Society holds records that tell us about those later years.

For one, he continued living in his rooms over the bank, the same ones he moved into after his divorce with Belle decades earlier.

“A visitor in the mid-1920s described the scene. ‘In those rooms there was something of the military spirit of the Colonel himself. Far into the years when a little sag in the shoulders would have been quite excusable, he held himself erect, always a soldier. There was a prohibition law then, but that did not prevent the Colonel usually having a little something with which to exhibit the hospitality becoming an officer and a gentleman.”

Times Observer photo by Josh Cotton/Photo courtesy of the Warren County Historical Society Above, Windsor purchased this plot of land at Oakland Cemetery when his mother died in 1906. In addition to Windsor, his parents and an aunt are the only family members buried there, according to the Waren County Historical Society. At left, a late in life photo of Col. Windsor at what we now know was Soldiers & Sailors Park in downtown Warren.

It’s unsurprising that military affairs dominated the discussions.

“And as one left, there was a sort of feeling that the door should have been a tent flap and on the outside an orderly standing stiffly at attention.”

While his business interests were as varied as the man himself, he struggled financially late in life as none of the schemes he had been a part of delivered the profits he anticipated.

Per the Historical Society, he approached county officials for a job in 1927 — “sealer of weights and measures” — and told the commissioners he “could fill the position and I think I deserve it, for what I had done for this county and state when I was financially stable.”

That job didn’t come to fruition and his meager prospects were obliterated by the stock market crash in 1929.

In 1931, he moved out of his rooms above the bank into a one-story residence at 411 Third Ave.

“By the 1930s, Fred was dependent on a monthly check from his generous brother, Arthur,” according to the Historical Society. “Fred spent his days quietly at home, but evenings found him at ‘his table’ in the Elks Club, drinking a spoonful of vinegar with each shot of whiskey and re-living the Spanish-American War with anyone who dropped by. In his declining days, his loyal housekeeper, Mrs. O’Connell, saw that he ate well and was comfortable. She recalled that as he dozed, he would sometimes call out plaintively for “Belle, Belle.” Once he sat up and shouted in his sleep, “Charge! Downhill! Downhill!”

In February 1936, per the Historical Society, Windsor was admitted to Warren General Hospital where he died 16 days later “alone, and virtually penniless.

“The whole town turned out for his funeral procession from the Episcopal Church to the Windsor plot in Oakland Cemetery… As the snow gently fell, the American Legion Bugle and Drum Corps escorted the caisson bearing his flag-draped casket, joined by the massive colors of all the patriotic and military organizations in Warren. 250 veterans marched behind — some coming from Jamestown, Oil City, Franklin, Titusville, Corry, Bradford, and Kane. Company I turned out in full strength, At the graveside, tributes were given by members of the Elks, the fire department, the Spanish-American War veterans, the American Legion, and the commander of Company I.

“An eight-member squad fired a rifle salute and Taps were played by two buglers, one standing out of sight over the rise playing the echo.”

Windsor was buried at Oakland Cemetery just inside the entrance on the side of the hill on Rt. 6. He rests at the foot of a giant stone he had placed to mark the Windsor family plot.

He’s buried there, according to grave records, with his father, Jairus, who died in 1914, and his mother, Helen, who died in 1906.

Any time one writes a biography, you know your subject is going to die.

Sometimes you know how the story will end.

You know one thing for sure, though — the subject is going to die.

And, in this case, it’s possible to look at Windsor’s last years and almost view him as a sad figure, one with all the potential in the world yet also one who died “virtually penniless.”

But the eccentric elements of the man that left him penniless may have been the same characteristics that made him so eminently interesting.

Either way, I’ll stand by my suggestion at the start of this entire series.

Fred Windsor gives the Dos Equis “Most Interesting Man In The World” a run for his money.