This most epic mug shot fail (or win): Former Big Dig boss Matt Amorello

Former Big Dig boss Matt Amorello has stretched out a really bad day over four years, culminating in one of the most humiliating mug shots ever taken.

In 2006 Amorello stepped down as Massachusetts Turnpike Authority chairman over major problems with the grand Central Artery rerouting project, or Big Dig, in Boston. Since then his marriage has disintegrated, he lost his house, and couldn’t find a job.

Things got even worse this Friday night / early Saturday when the 52-year-old former chief was so plastered he was alledgedly urinating on himself in public. Later that same night he got behind the wheel and smashed into two parked cars. Police saw this happens and caught up with him in a Dairy Queen parking lot, where they had to pepper spray him to get him out of the car.

Later, when he was booked he passed out and officers had to physically hold his head up to get the booking shots. A warrant was issued for his arrest when he failed to show up in court Monday, but his family sent the police a statement that he’s being hospitalized, even though no hospital record currently exists for him.