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We don't know what was happening during the creation of these monstrosities, but we can still imagine.
Milwaukee, Wisconsin

Flag Designer: "I'm sorry sir I can't incorporate wheat, the skyline, a boat, 1846, a smaller flag, a knight, three swords and a gear into one flag"
Mayor: "Well why not?"
Flag Designer: "Well here's a draft and as you can see there is just too mu-"
Mayor: "That's perfect! Way to go, I'm going to give you a huge bonus"
Flag Designer: "B-but... thank you?"
Philadelphia, Pennsylvania

City Official: Okay things look great, love the colors, love the diversity love the, wait? IS THAT A SEVERED HUMAN ARM!"
Clearly High Flag Designer: "I know right? I can't believe the mayor approved this hahaha"
San Francisco, California

Mayor: "Looking back on it, I really regret doing a citizen submitted flag design right when Clip Art came out in 1998'"
Woodbury, Minnesota

Flag Designer: "Oh shit, you guys are an actual city? I thought that was just some weird name for a tech company."
Mayor: "Well we've already spent two million dollars on you so I guess this is our new flag"
Montgomery, Alabama

Mayor: "Just to make things clear, as close to the confederate flag as you can make without actually being a confederate flag"
Designer: "So just add gray, take away one blue bar and rotate it a few degrees"
Mayor: "Perfect"
Provo, Utah

Mayor: "I said we would use your vitamins in our cities medical clinics, I never said you could redesign our fucking flag"
President of Centrum Silver Vitamins: "You know we've already printed two thousand flags, it's a little too late to go back on this"
Mayor: "Sigh, fuck it we'll keep it."

Jimmy Rippert is co-founder/Co-CEO/Unpaid intern of Delusional Suspects. Follow him on twitter @Fishboyjim or don't, but please do.