This is the flag of the City of Milwaukee.
It's a cluttered mess of symbols representing the city's history, culture, industry and architecture. Among other things.
In the upper-left quadrant of the gear, we find an image of a red-skinned Native American wearing a headdress. Officially, that's there as a tribute to the tribes who first settled the region, but many have singled it out as being more a tip of the (baseball) cap to the Milwaukee Braves. There's a certain amount of sense to that, since the flag was designed in 1953 and 1954, when the Cream City was absolutely crazy about her brand-new Braves.
Makes me wonder; if the flag had been designed just a few years earlier, when the Brews were the city's beloved baseball team, might we be seeing a slightly different flag flying today?