Did you know Cy was in prison, not sure why

Kagavi

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Came across this shirt graphic today, probably from the 1970s-80s. It seems to show Cy breaking out of prison, but the more I look at it, maybe he's breaking INTO prison to take revenge. Trying to think of scenarios. Anyone seen this design before?

bafkreie5hafmxl7cbxvniei5ig25wbvjobczv2i4hqtrq726g6od34hufi@jpeg
 
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Also found this...looks to be from the 50s. And maybe drawn by my little sister. (If I had had one)

Postcard-Iowa-State-University-Cyclone-Mascot-pic-1A-2048-8bfa6de3-f.webp
 
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Came across this shirt graphic today, probably from the 1970s-80s. It seems to show Cy breaking out of prison, but the more I look at it, maybe he's breaking INTO prison to take revenge. Trying to think of scenarios. Anyone seen this design before?

bafkreie5hafmxl7cbxvniei5ig25wbvjobczv2i4hqtrq726g6od34hufi@jpeg
This looks like Cy breaking out of a basement bar or apartment or academic building.
 
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Looks most likely it has something to do with a "Breakout Season" in something.
 
Yeah. I think he got off for being “forced” by some bigger dude. Too lazy to look it up but he got lucky
Bigger dude was an ISU FB player. Levin White had a .22 rifle and Mack had a knife. The Mack the Knife jokes wrote themselves.

They cops got them because one BK employee jumped out the drivethrough window - before the rest of the employees were locked in the walk in cooler - and went over to the doughnut shop and found some cops. The cops in the doughnut shop jokes also wrote themselves.