From that, he went to stripping tobacco, but he found time to attend school and also to enroll at a business college.
He spent several years in Cincinnati learning the clothing business and then came to Chicago where he was employed as a retail salesman by the Barbe Bros. clothing house. In 1880 he embarked on the clothing business on his own account with his brothers at 183 W. Madison Street in Chicago.
In 1896 he opened his establishment at 160 S. State Street. His brothers Benjamin, Edward, and Harry took employment at Woolf's Clothing Store.
Isaac Woolf decided it was time to give something back. He decided to provide a full Thanksgiving dinner with all the trimmings for any and all newsboys in Chicago who wanted to attend.
The tradition began in 1882 when owner Isaac Woolf invited about a hundred newsboys to join him for Thanksgiving dinner. Called “newsies,” the boys were employed as the main distributors of newspapers to the general public. Typically earning about thirty cents a day, they were wretchedly poor, often sleeping on the streets.
Having been a penniless newsboy himself, Woolf understood their plight and that of others who were impoverished. Paying for the meals out of his own pocket, the kind-hearted retailer expanded his annual dinner to include other poverty-stricken families and destitute elderly couples, as the ranks of the poor swelled during the severe economic depression called the Panic of 1893.
On March 17, 1898, Isaac Woolf opened his grandest store yet at the southwest corner of State and Monroe, Chicago. He billed his store as "The store with a horseshoe over the door and the Palmer House over the way."
For twenty-four years Woolf, president of Woolf's Clothing Store closed early on the day before Thanksgiving, as it had done for years, in order to get ready to serve a holiday dinner for the poor of Chicago.
Woolf died after 2 days of sickness on October 21, 1906. Woolf Clothing Company was in trouble without Isaac at the helm. Within two years, Woolf Clothing Company filed for bankruptcy.
Compiled by Dr. Neil Gale, Ph.D.