Teddy Roosevelt’s Near-Death Experience in Western Mass.

I recently read Paulo Coelho’s The Alchemist. In it there’s a brief exchange between a young shepherd who’s wrestling with the idea of pursuing his life dream, and a wise old man who eggs him on.

The exchange goes like this:

“What’s the world’s greatest lie?” the boy asked, completely surprised.

“It’s this: that at a certain point in our lives, we lose control of what’s happening to us, and our lives become controlled by fate. That’s the world’s greatest lie.”

The idea of fate as a catalyst in American history is peculiar. For decades following the country’s founding, the American experiment was largely considered to be by design. In some eras, perhaps even today, it was thought to be sanctioned by God. Conversely, Americans can feel uncomfortable with the idea that their country and their national history are not driven explicitly by them, the people; fate takes control out of their hands and leaves the future up to chance—it’s unsettling to have no autonomy over your life and its direction.

But we’re hard pressed to consider the presence of fate when it comes to some of America’s most notable figures. Imagine if George Washington had not dodged at least four bullets in the French and Indian War, more than 30 years before he became the first president? Where would we be today had he not defied death?

Since Washington, no other president has looked death in the face and lived to tell the tale more often than Theodore Roosevelt. (In 1912, Roosevelt famously delivered a 50-page speech more than an hour long after he was shot in the chest with a .38-caliber revolver.) Can we really say fate was not at play when he nearly died in Pittsfield, Massachusetts?

Fate, it seems, breathed life into Roosevelt. He could’ve died from chronic asthma as a child, he could’ve succumbed to despair when his wife and mother died on the same day. At the turn of the century, he ascended to the presidency after an assassin’s bullet cut down incumbent William McKinley in Buffalo, NY. Roosevelt’s climb up the ladder of governance was both improbable and inevitable. It was as if the laws of nature were bent to provide him his high station in history; Roosevelt himself was a force of nature.

Roosevelt was less than a year on the job as President of the United States when he departed his home at Oyster Bay, NY for an almost two-week tour of New England. The tour was supposed to mark a new beginning, a fresh start to put the nation’s mind at ease following the murder of McKinley—the third president assassinated in just over 30 years. As such, the train car Roosevelt rode to New Hampshire to kick start the tour was appropriately called Mayflower.

He and his security detail rode the rails to New Hampshire, Maine, and Massachusetts.  From here he was to depart for Connecticut, cross Long Island Sound, and arrive safely home at Oyster Bay.

Wednesday, September 3, 1902

7:45 a.m.

In the Western Massachusetts town of Dalton, Roosevelt met up with Governor Winthrop Crane. In Dalton, the manufacturer Crane & Co. (namesake of the governor) produced the cotton-based paper used for American currency. Here Roosevelt, Crane, Treasury Secretary George Cortelyou, and Roosevelt’s personal secret service agent William Craig boarded a carriage for nearby Pittsfield, a small yet thriving industrial city. Mckinley had made multiple visits to Pittsfield during his tenure in office.

The weather was pleasant and fair. Pittsfield was abuzz with excitement and anticipation. The center of town was decorated for the occasion. Factories and mills blared bells and whistles when the president crossed into city limits. Locals gathered en masse to hear the celebrity-politician speak, to witness his famous energy; Roosevelt delivered a familiar stump speech. He and his companions then started for the Pittsfield Country Club for a round of glad handing before stopping in nearby Lenox and Stockbridge.

They never made it.

Roosevelt’s landau carriage/ Theodore Roosevelt Collection, Houghton Library, Harvard University

8:20 a.m.

Pittsfield Mayor Daniel England notified the city council that he had requested the Pittsfield Electric Street Railway to discontinue operations on North and South Streets until the departure of the president. All motorcars were restricted from operating within an assigned, roped-off area downtown. Police officers were asked to keep an eye out for motormen who might drive against these instructions, and to remove them as necessary. These rules were all made verbally and no written record was kept.

At the request of the director of the Pittsfield Country Club, the railway superintendent allowed the South Street motorcar to run below the roped-off area. The superintendent did not notify security of this concession.

8:30 a.m. – 9:30 a.m.

Mayor England asked local business to suspend operations, and for those residing along the president’s route to decorate their storefronts and to display the American flag; and whoop “three cheers for Theodore Roosevelt!”

9:15 a.m.

Roosevelt finished his speech and he and his entourage made way from downtown Pittsfield to the country club, stopping briefly to call upon former senator Henry Dawes. Their vehicle was a four-horse landau, a luxury carriage. The driver, D.J. Pratt of Dalton, sat in the front-right. To his left was Craig, the secret service agent. In the backseat, Roosevelt sat on the right behind the driver. To his left was Governor Crane. Secretary Cortelyou sat opposite them, his back to Pratt and Craig in the front seat. Pratt and Crane were well acquainted. Crane always called on Pratt to drive for events like these. Pratt owned the landau and the horses, and knew how to handle them.

Following Roosevelt’s landau were additional carriages full of his staff, including his physician Dr. Lung.


Euclid “Luke” Madden, motorman of the 60-horsepower No. 29 Morningside car (without air brakes), was operating between the country club and the Stanley Works factory along South Street. He was aware of the president’s visit and the disruption it would cause. Madden was due at the country club at 9:45 a.m. and as far as he knew, his trolley was under no special orders to delay or reroute. He continued on per usual, picking up passengers along the way.

His route crossed two hills, between which was a culvert spanned by a railroad bridge. Madden descended the first hill and crossed the bridge, claiming to have applied the air brakes and exercised all caution. By his estimates, the trolley was moving no faster than 8 m.p.h. His view was partially obstructed by the carriages of the president’s staff and the swarm of spectators lining the road.

At this point, the caravan of carriages and the trolley were all proceeding in southward direction. That put the carriages on the right side of the road and the trolley down the center. Still ahead of the trolley, the landau approached the same culvert. Here the road crosses over the railroad tracks.

Pratt’s gaze was also obscured by the escort carriages. He was under the impression that he had the right of way, given the restrictions on streetcars that day, and was unaware of any permissions granted to the South Street motorcar.

It’s unclear if Madden really did apply the trolley’s brakes. He quickly passed the escort carriages and caught up to the president’s. Madden did, however, sound an alarm bell on the trolley that alerted passengers to impending danger. The commotion perked the ears of agent Craig, who stood up to inspect the situation. Secretary Cortelyou likewise stood up. Roosevelt claimed to have heard the gong as well. Craig, Cortelyou, and Governor Crane all caught sight of the trolley at the last second and tried to wave it off. Then…

Roosevelt’s landau carriage/ Theodore Roosevelt Collection, Houghton Library, Harvard University


Pratt turned his horses left to cross the tracks. The trolley struck the landau at a 45-degree angle. The force of the impact was so powerful it smashed and splintered the landau. At least one horse perished. Roosevelt, Pratt, and Cortelyou were all hurled from the carriage; Roosevelt was tossed some 30–40 feet away. Crane was fortunate and emerged unscathed.

Pratt was hospitalized. Cortelyou smashed his nose on the door of the carriage. Roosevelt landed on his face and tore open his leg. His clothes were shredded, his hat crumpled, his spectacles shattered.

Craig was not so lucky. This would mark the first time a secret service agent died on the job. His death was particularly gruesome. The collision flung him onto the track in front of the trolley. His skull and upper torso were crushed beneath the wheels of the motorcar.


Madden, the motorman, was arrested along with the conductor of the motorcar. The president of the railway posted $7,500 bail for the two men (almost $220,000 in today’s currency when adjusted for inflation). Charges against the conductor were eventually dropped but Madden was found guilty of manslaughter and sentenced to six months in a house of corrections and a $500 fine (almost $15,000 today). He paid the fine and only had to spend his days doing prison laundry; he was allowed to spend his nights at home.

Roosevelt tried to conceal his injuries from the public, typical Roosevelt machismo. Despite assuring everyone of his health, including King Edward VII, a bacterial infection set into the wound on Roosevelt’s leg. On September 23, he underwent surgery to treat a buildup of fluid beneath the scar tissue. A week later, there was more buildup and this time he came down with a fever. He required a second surgery.

Roosevelt carried these injuries with him the rest of his life. In letters written years later, he’d remark on the affect the accident left on his overall health. During his expedition to the Amazon, where he and a large party explored the River of Doubt, he gashed his leg and came down with an infection. His old Western Mass. injury echoed in the tremendous pain he now suffered.

In 1905 Roosevelt paid a second visit to Pittsfield. His successor, William Howard Taft, visited Pittsfield and delivered a speech on the city’s 150th anniversary  in 1911.

Roosevelt died in 1919 at the age of 60.

But imagine how different the world would be if he hadn’t survived that fateful day in Pittsfield. When he took over after McKinley, Roosevelt did not appoint a vice president. If he perished in Pittsfield, per the line of succession Speaker of the House David B. Henderson of Iowa would have assumed the presidency. Who was Henderson? Exactly. We don’t remember his name today. But perhaps we would have if fate hadn’t intervened in September 1902. Henderson ultimately stepped down from the speakership in 1903; would he have stepped down from the oval office had he been elevated to occupy it? And Roosevelt, widely regarded as one of the most popular presidents of all time, may have been a mere holdover between two administrations, a footnote on the pages of American history.

Boltwood, Edward, “The History of Pittsfield, Massachusetts: From the Year 1876 to the Year 1916” Eagle Printing and Binding Co. [City of Pittsfield; Pittsfield, MA] 1916.
Boston Daily Globe (1872-1922) ; Boston, Mass. [Boston, Mass] 04 Sep 1902
Vermilyea, Peter C.; DeMazza,  Michael S, “A Damnable Outrage’: Theodore Roosevelt’s 1902 Streetcar Accident.”  American History. August 2005.

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