In December of 1964, 5th Ward Alderman Leon Despres shared his predictions for the new year in the Hyde Park Herald. First among his predictions was this: “Jimmy’s Tavern will still be on 55th Street at the end of 1965.”¹

And indeed it was. Jimmy’s survived urban renewal, even survived Jimmy himself, and throughout its tenure has proven itself practically immovable. Jimmy’s first opened its doors in 1948, after James “Jimmy” Wilson (the bar’s namesake) decided he wanted to own his own bar after some time as a bartender at University Tap (located where Campus North Residential Commons is now).²

When Jimmy took over the space at 1172 E 55th Street, there was minimal renovation to be done – it was already set up as a bar, since the previous tenant had been the tavern Little Tom’s Place (named after its owner, Thomas Wallwin). Despite its convenience, however, the building had an ill-omened history: in 1944, Little Tom’s Place was the site of a murder-suicide involving the owner and bartender.³ Little Tom’s place would—understandably—sit empty for the next four years, until Jimmy came to open Woodlawn Tap. The day the bar put up “Woodlawn Tap” on its façade may well have marked the first and only time anyone called it by that name. Although Jimmy was always adamant he wanted his bar to be Woodlawn Tap, his patrons were equally adamant about calling it Jimmy’s. It was part of the magic of the place: there were countless bars lining pre-urban renewal 55th Street, but you went to Jimmy’s for the man himself.

What may have ultimately saved Jimmy’s from the otherwise nearly complete reinvention of 55th Street during the 1960s was its next-door neighbor: the Lutheran Theological Seminary. The Seminary had originally intended to build its main campus on the 5400 University-Woodlawn block,⁴ which it had acquired (Jimmy’s included), but stiff opposition by the block club caused them to build it on Greenwood-University instead – meaning there was no real reason to get rid of Jimmy’s, and really no benefit to the Seminary to do so.⁵

Jimmy’s was (and is) enough of a neighborhood institution that it beat the Liquor Control Commission on two occasions: first in 1952, the bar’s liquor license was revoked for serving alcohol to a minor. There was so much public outcry that Mayor Kennelly himself ended up reversing the decision.⁶ When Jimmy died in 1999, his sons found out their application to renew the bar’s liquor license had been denied because of Jimmy’s proximity to St. Thomas the Apostle Catholic Church.⁷ Even this couldn’t keep it down. The decision was reversed in March of 2000;⁸ Jimmy’s was open again in May.⁹