GLENWOOD TAVERN, CHICAGO — Like many bars within the Chicago area, Glenwood Tavern has become a staple of its neighborhood. The space gained notoriety for their craft cocktails and especially for their pool table. On any given day during the week, if you were to look at the pool table, all challengers would likely be playing a single man. Local Pool Shark Cliff Finley is yet to be defeated within the walls of The Glenwood. But despite his cool and calm demeanor on the table.