Directly across from the park, at Nicollet and Second Street, one employment agency formed what was left of the city's day labor headquarters: the "slave market.'' By the 1950s, most men on skid row were too old to work. But out of habit or tradition, employers still backed their trucks up to the curb at Gateway Park when they wanted to hire casual laborers, and for the pensioners, watching these transactions offered a favorite form of entertainment.

A number of businesses unrelated to the daily lives of skid row residents also operated in the area, either because they had been established earlier, or because they were attracted by low rents. Estimates of the actual number of businesses on skid row at the outset of redevelopment vary. One study puts the number at roughly 300, another at 408, and a third at 527. In 1955, before any concrete redevelopment plan for the neighborhood had been adopted, the city directory contained nearly a thousand listings for the blocks the Gateway district comprised (including the site of the public library, which was cleared just prior to the federal slum clearance project). These listings show an astonishing diversity of uses. In addition to roughly sixty hotels, fifty bars, twenty liquor stores, sixty cafes or restaurants, and fifteen pawnshops, the area contained some eighty wholesale distribution and supply companies (moving inventories that included novelties, fruits and vegetables, and drugs; and specialized equipment for laundries, funeral homes, and photographers), forty manufacturers (of items including plastics, springs, overcoats, hearing aids, envelopes, and clothing), and close to 350 service businesses (including lawyers, accountants, surveyors, artists, travel agents, stenographers, barbers, watch repairers, knife sharpeners, and detectives). More than one hundred retail shops in the neighborhood sold jewelry, furs, clothing, lamp shades, antiques, cigars, tents, furniture, artificial limbs, or books. Some two dozen clubs and associations kept their headquarters in the Gateway, including half a dozen labor unions, the Kiwanis and Rotary clubs, the Moose Lodge, the Eagles, and associations of writers, readers, porters and waiters, and co-op elevator operators.

Despite this broad array, skid row vice, dereliction, and drunkenness drew the most attention in the early fifties. These had been a feature of the neighborhood for decades, but had been more or less tolerated so long as the district also served as the migrant-labor headquarters of the Upper Midwest, offering a ready supply of cheap labor to the most important industries of the age. But after the war, the commercial nature of the city shifted and, with it, attitudes toward skid row.