History is full of presidential anomalies: James Buchanan is the only president to remain a bachelor for his entire term. Woodrow Wilson is the only president to have a doctorate. Gerald Ford is the only president to hold a prom in the White House. And George W. Bush is the only one to have run a marathon. Then, there’s Grover Cleveland—the only U.S. president to have served as an executioner.

“Big Steve,” as he was known back then, took the lives of two criminals when he was the Erie County Sheriff, a position he was elected to in 1870. The first to meet the hangman’s noose under Cleveland was 28-year-old Patrick Morrissey, who had been convicted of murdering his mother with a bread knife during a drunken disagreement about money.

Knowing that Sheriff Cleveland had been wrestling with doing the deed, Deputy Richard Harris volunteered to do it for him. “Big Steve” had the right to appoint a surrogate executioner for $10, but Cleveland declined in the end, feeling he should hand down the punishment himself.

On September 6, 1872, the future president pressed the lever that released the trapdoor under Morrissey. “... this little tragedy made Mr. Cleveland a sick man for several days thereafter,” The New York Times [PDF] later reported—and, unfortunately, he had another one looming.

The second execution went even worse. John Gaffney had been convicted of fatally shooting a man in the head while playing cards at a saloon. As with Morrissey, Gaffney was sentenced to die by hanging. Once again, Cleveland insisted on carrying out the punishment himself. Unfortunately, when the sheriff pulled the lever, the 5-foot drop broke Gaffney’s neck but didn't kill him. It took the man 23 minutes to die.

Cleveland held the job for just one term before returning to his career in law, but he couldn’t leave the executions behind entirely—when he ran for president, his opponents dubbed him the “Buffalo Hangman.”

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