Rascals and Rogues: Louis “Louie the Dip” Finkelstein

During my travels, adventures and travails in 1950’s and 1960’s Cleveland, I got to know a quite few people who fit into the categories of “Rascal” and “Rogue” very well. Let me tell you about some of the most interesting ones who could be found mostly on Short Vincent in those days.

Louie the Dip
A Jan. 10, 1964 “Time Magazine” article announced the death of Louis Finkelstein, AKA “Louie the Dip,” another regular visitor to my store:

“Died. Louis ("Louie the Dip") Finkelstein, 73, king of the nation's pickpockets, a dapper, Ukrainian born master of petty larceny who gleefully boasted of paying $8,000 a year in fines, court costs and lawyers' fees, was arrested a record 121 times in Cleveland alone, once being nabbed with his fingers in the pocket of the police chief, another time with the wallet of a reporter covering his trial, but alas, spent his last years in retirement and on relief after arthritis robbed him of his touch.  He died of a heart attack; in Cleveland.”
Louie the Dip was known as Cleveland's prince of pickpockets. His 50-year career record of more than 120 arrests and 20 prison sentences served made him the most frequently arrested pickpocket in Cleveland's history.

Born in 1891 in Odessa, Ukraine, Louie’s first arrest in Cleveland occurred in March 1909, at the age of 18, for picking a woman's purse in the Grand Theater on East 9th Street. Between 1909 and 1915, Finkelstein was arrested three times, serving terms in the Ohio Reformatory and the ClevelandWorkhouse.

Between 1915 and 1933 Finkelstein was arrested 46 times, and convicted 23 times, for numerous offenses.

The highlight of this period occurred in 1933 when he picked the Parma police chief’s pocket and once spent a Saturday night in two jails in Chardon and Cleveland.

Finkelstein picked his bail bondsman's pocket, and even that of a reporter covering one of his trials.

Sentenced to the Workhouse in 1933, Finkelstein escaped but was recaptured in New York while working the crowd at a revival meeting. Convicted of grand larceny, he was given an eight-to-10-year sentence at Sing Sing prison in Ossining, New York.

The U.S. government unsuccessfully attempted to deport Finkelstein as a habitual criminal.

Paroled in 1941, Finkelstein returned to Cleveland and the Cleveland Workhouse. A 1942 City investigation found that Finkelstein was the Workhouse “boss,” avoiding all tough jobs and arranging for money and favors for prisoners. In 1954 arthritis forced Finkelstein into early retirement. He tried gambling but failed. He died a broke man and is buried in Chesed Shel Emeth Cemetery on Ridge Road.

His obituary and adventures say it all. Although Louie the Dip was a frequent visitor to my store, mothing came up missing after he visited (that I’m aware of)!

Ralph Horner
Ralph Horner

About the Author: Ralph Horner

Ralph Horner grew up in the 1950s and 1960s on Whittier Avenue in the Central and Hough neighborhoods. In the 1960s and 1970s, at the age of 19, he managed a French Shriner shoe store on Euclid Avenue, where he got to know many of the people who hung out on Short Vincent.  A self-proclaimed juvenile delinquent living in the inner city, Horner observed the characters who were regulars in the neighborhoods he lived and worked in. Now in his 70s, Horner shares the stories of some of his more memorable experiences on Short Vincent with the FreshWater series, Rascals and Rogues I Have Known.