He closed the door behind him, pocketed the key, and walked off whistling. Jailers these days were so cocky, thinking that a set of modern steel bars gave them an almost carefree power over their prisoners. Steve knew better. And he was going to show them just how little bars actually mean to a master.
The first escape was simplicity itself. Steve had come in with a perfect long wire woven into his shaggy hair. A quick lock-pick and he was out. The lone guard, Marsden according to his nametag, was dozing. A Midwestern town holed up from the rain, didn't notice a shaggy man stashing an orange jumpsuit in the outside dumpster.
The next day, around noon, Steve strolled into the county jail, dressed in a fine wool suit, smoking a nice Cuban and clean shaven. He'd had some rather profitable times the night before; his prison boots had left muddy prints at every house on Main Street, it seemed. As Steve casually stripped down to his boxers and changed into the orange jumpsuit that they'd provided, he joked with an astonished Marsden. "I needed a shower and a shave, you know how it is. The rain was a welcome relief, until I got wet." He whistled as they led him to his cell.
A few weeks later, they'd gotten a new warden. A little while after that, on a warm Wednesday night, Steve was ready to make his second break. With a carefully secreted rock from the exercise yard and five years of experience pitching in little league, Steve tripped the alarm system. The jail was one of those newfangled electrical deals that double locked all the cells as soon as the alarm was tripped. One part of his excursion a month earlier was to switch a couple wires. His cell door clicked unlocked within an instant and he slipped out. Jackson came running, yelling for him to stop, reaching for his gun. It didn't help that he should have been wearing pants. Wednesday nights, as pretty much everyone in the jail knew, Jackson's lady friend, Samantha, came over. Steve had waited until her squealing had reached that particularly high note before pulling his little stunt and his timing had paid off splendidly. As Jackson turned a fantastic shade of red, Steve waltzed out, switched off the alarm, blew a kiss to a gasping Samantha, and liberated a few bills from the confines of a convenient wallet. Jackson resigned the next day. He was thoroughly embarrassed, while Steve changed into yet another orange jumpsuit, making obscenely suggestive gestures indicating a certain short length on camera.
Steve was under maximum security now. The county wasn't about to be a national laughing stock for a third time in a row. At the same time, they weren't going to bow in and send him over to the state prison. Instead, there was a 24 hour security detail pretty much right outside his cell and these new guys looked business. They just hadn't anticipated a little outside help. As Steve escaped through a freshly gaping hole in the prison's plaster roof, a single yellow note came fluttering down on top of the debris.
"Thanks for the jumpsuits and the housing guys. I hope you had as much fun as I did. PS. Please learn a new song to whistle other than I'm a little teapot." The postscript had been hastily scribbled.
Currently grooving to: Santana - Everybody's Everything