Michael Frank Simon has had numerous run-ins with police for breaking into places. But it's his breakout that people will remember most.

Simon apparently busted through a window on an upper floor of the Hennepin County jail in downtown Minneapolis before sunrise Wednesday, landed on a lower-level rooftop then ran across the top of a skyway to a parking ramp. Officers searched the ramp and surrounding areas but failed to find Simon, who was wearing an orange jail jumpsuit and blue jacket.

Simon, 57, of Hopkins, made his way to the St. Paul suburb of Little Canada, where he was arrested by federal authorities three hours later.

The details of how Simon pulled off his brief escape and then made it all the way to Little Canada, some 12 miles away, were still a mystery late Wednesday, with Hennepin County Sheriff's officials declining to comment or reveal how they managed to nab Simon.

But a broken window on one of the jail's upper floors was boarded up soon after Simon got away, and a source close to the case said that he had fled through that opening.

A repairman replaced the window by early afternoon.

Michael Frank Simon

Simon's escape was the first at the Hennepin County Public Safety Facility, across the street from City Hall and kitty-corner from the Government Center, since the building opened in 2001, said Jon Collins, a spokesman for the Sheriff's Office.

Simon's criminal history spans nearly all his adult life and includes at least 15 convictions for burglaries committed around the Twin Cities area. He was booked into the jail on Sept. 25 on suspicion of financial transaction card fraud, according to the Sheriff's Office.

His breakout Wednesday occurred about 7 a.m., officials said.

A witness reported seeing "somebody running across the top of the skyway from the jail toward the Haaf [parking] ramp."

A surveillance camera spotted Simon heading southeast on S. 3rd Street, and emergency dispatch audio said that the escapee was wearing an orange jail jumpsuit and dark blue jacket at the time he fled.

Another officer said a witness reported that officers searched the nearby Haaf and Gateway parking ramps as well as an area south of downtown along the Mississippi River. A spokeswoman for the Gateway ramp confirmed it was briefly closed but declined to say more.

Collins said that Simon was caught about 10 a.m. in Little Canada, and was being held not at the jail but at the far more secure Oak Park Heights state prison for violating terms of his supervised release in connection with a 2016 burglary conviction.

Sheriff-elect Dave Hutchinson told the Star Tribune that Simon was in the custody of the U.S. Marshals Service.

Simon had pleaded guilty to two counts of burglary and was expected to receive a sentence of 2½ years on Dec. 19. The Hennepin County Attorney's Office said that his brief escape won't affect the terms of his plea deal.

Simon left prison six months ago, with permission, and went on supervised release stemming from a 2015 burglary conviction in Hennepin County. He broke into an office complex in Bloomington and made off with two big-screen TVs and other electronics, $23 in cash and a bottle of whiskey.

In the case for which he was most recently booked, Simon allegedly broke into the Institute for Orthopedics and Chiropractic in Edina on Sept. 15 and stole a credit card from a desk.

He also allegedly broke into another office in the same building and stole four laptop computers and numerous medals from the Minnesota Golf Association.

He allegedly used the credit card numerous times into the next day at several gas stations, and approached two strangers to put gas in their vehicles with the card while accepting a lesser amount from them in cash.

When he was arrested at a McDonald's in Minneapolis, police found burglary tools in his vehicle.

Simon also has been convicted twice for theft, twice for forging checks and once each for receiving stolen goods, property damage, assault and drug possession.

Star Tribune staff writer Rochelle Olson contributed to this report.

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