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Chicago Tribune
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Around 9 p.m., Matthias Schaffer, the watchman on duty in the Courthouse tower, was scanning the Chicago skyline when he spotted flames on the city’s Southwest Side. Peering through his spyglass, he mistakenly guessed the fire to be near Canalport Avenue and Halsted Street. Schaffer called down through the voice tube to William J. Brown, night operator at the central alarm telegraph office on the Courthouse’s first floor. Schaffer told Brown to strike Box 342, which was more than a mile away from the O’Leary barn and in a different fire district.

Brown sounded the alarm, and seconds later the Courthouse bell was ringing out 3-4-2. Schaffer scanned the skies again and quickly realized his error. He called Brown once more and told him to strike Box 319, which was much closer to the fire and in the correct district. Brown refused, saying a second alarm would only confuse the firemen and that they would pass the actual fire on their way to Box 342. Because of Brown’s actions, two well-equipped steam engines in the O’Leary’s district ignored the alarm and remained in their company houses.

Meanwhile, John Dorsey, foreman of the America fire hose cart company, was at the fire house at 31 Blue Island Ave. when he spotted the flames from the O’Leary fire. Dorsey and Dave Manwell, the company’s hoseman, hitched up the horses and headed toward De Koven Street. The America was the first fire company to arrive at the O’Leary blaze.

On Maxwell Street, six blocks south of the fire, Joseph Lauf was on watch in the tower of the Little Giant Company No. 6. He sighted the O’Leary fire and notified his foreman, William H. Musham. As the company was preparing to pull out, the alarm for Box 342 sounded inside the fire house, but Musham was not fooled. They headed straight for the O’Leary barn.

When the Little Giant arrived, a half-dozen houses and barns on De Koven Street were in flames. Within an hour, seven other companies found their way to the fire. The firemen lined up their equipment to contain the growing flames, but an increasingly strong wind from the southwest blew burning embers over their heads, starting new fires behind them.

Musham tried to contain the destruction to the O’Leary block, but looking upward he saw a sky full of flaming debris falling like fiery snowflakes all over the neighborhood. The swirling sparks were spreading the fire to the north, consuming house after house until the flames roared out of De Koven Street and reached the north side of Taylor Street.

Fire Marshal Robert A. Williams arrived at the scene and assessed the situation. The fire was still not out of control, but his men and equipment were being stretched thin. Williams wanted to head off the flames to the north, but he knew there was a danger that the fire would double back against the wind and move farther south, so he stayed in position.

The fire, however, kept advancing northward. It reached Ewing Street before Williams decided to send a company to get in front of the flames and stop its progress.

While his forces were split, the marshal’s fears were realized. The fire fought against the wind and marched even farther south. Although it was not yet as large as the Saturday Night Fire, the O’Leary blaze was now big enough that it required the entire fire department to subdue it.

From his home at 574 Halsted St., former Chicago Alderman James H. Hildreth heard the alarms and rushed out toward the O’Leary barn to see the flames. Hildreth thought that the situation was getting out of control and suggested blowing up a line of buildings in the fire’s path to halt its advancement.

Williams told the meddlesome ex-politician that the fire department had neither the authority nor the explosives to destroy people’s homes. Undeterred, Hildreth found some explosive powder on his own and spent the next 24 hours bombing buildings, but his efforts to stop the fire were unsuccessful.

Meanwhile, Gustavus English, a police reporter for the Chicago Tribune, was leaving work when he heard the alarms and spotted the fire from across the Chicago River. He caught a cab and observed the flames rapidly devouring the West Side. He returned to the Tribune building and found the city editor, Sam Medill. Medill wanted to know where the fire was.

“Everywhere,” English said.

“Write it up,” Medill replied.