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The undersheriff in office when Cleveland took over was William L. G. Smith, a Democratic lawyer who had earned a national reputation as the author of Life at the South, or “Uncle Tom’s Cabin” as It Is, a pro-slavery plantation novel published in 1852 as a “refutation” of Harriet Beecher Stowe’s famous book. In Smith’s work, slaves were loyal and content and their masters benign. The villain was an abolitionist from the North who worms his way into the confidence of Tom the black slave and convinces him to escape to Canada. Tom realizes the error of his ways and returns to “good Old Virginia.” Somehow Cleveland was able to look beyond Smith’s politics and see an able, if fussy, administrator who could keep the sheriff ’s office running like an efficient machine. “You could set your watch by the time he arrived and departed from the office,” went one depiction of Smith—“precise in every word and action.” So exacting were his daily routines that it was said Smith would never deviate from the number of steps it took him to get from his house to the office. It was the same every day—“without clipping off an inch.”

Cleveland reappointed Smith, and it may have been a shrewd thing too, because Cleveland seemed to have very little interest in the routine duties of the sheriff. He delegated most of the day-to-day administration to the under-sheriff; meanwhile, he played. Weather permitting, he would go hunting or fishing with a buddy, usually Oscar Folsom, a young lawyer he came to feel as close to as a brother. If Folsom was busy, Cleveland rounded up Louis Goetz, owner of a Buffalo pub known as the Dutchman’s. Goetz’s saloon was located behind City Hall, at 194 Pearl Street, in the heart of the county office buildings and across the street from Democratic Party headquarters. The geography made the Dutchman’s a favorite hangout for Democrats.

Goetz served steak at the saloon, but the specialty of the house was bluefish when it was in season, sent directly from the Fulton Fish Market in New York City. Sometimes, after Cleveland and Goetz went fishing, they would return to the saloon, and Cleveland’s catch would be served for dinner.

Goetz worshipped the new sheriff and called him what sounded like “Grofer” in his German accent. He even hung a full-length portrait of Cleveland in the saloon, directly above the grill. During Cleveland’s tenure the Dutchman’s became a kind of annex of the Erie County Sheriff’s Office. In the back room, Cleveland’s cronies would gather for ale and song, and Cleveland himself, using a stein as a baton, would lead the chorus. In his rich baritone, he would begin, “There’s a hole . . .”

“There’s a hole,” the choir answered.

“There’s a hole,” sang Cleveland.

“There’s a hole,” responded the choir.

“There’s a hole in the bottom of the sea,” went Cleveland.

They could go on for hours like this. And the song would not end until everyone had emptied their steins.

The legal closing hour in Buffalo was 1:00 a.m., but rank had its privileges, and for Cleveland, Goetz’s would remain open until the wee hours. Soon, so would the other saloons where Sheriff Cleveland took his ale. He was playing cards at Blume’s saloon with Oscar Folsom and two other lawyers when the proprietor pointed to the clock. It was two in the morning.

“Now, boys,” Blume said, “take one more drink—on the house. I have got to close up, or the police’ll be after me.”

Cleveland, as the chief law enforcement officer in Erie County, had a good laugh over that one. Then he raised his mug and started singing—what else!—“There’s a hole in the bottom of the sea.” They had the next round on the house, and several more after that.

Sometimes, Louis Goetz failed to appreciate Cleveland’s brand of humor. One time, around midnight, Cleveland dropped by the Dutchman’s and found Goetz asleep. No one else was there. It was almost too good to be true. First, Cleveland set the clock ahead two full hours. Next, he found two Buffalo cops