Why, yes, the tale of Ryan Leaf can get sadder. For proof, here is his latest mugshot, snapped yesterday before he was released from a Montana prison. Leaf, once the man with the arm that could not fail (except it did), now kinda looks like a sad dad. A really sad dad. Oh boy, this is sad.

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His prison stint started in June 2012 following guilty pleas in a case that the Los Angeles Times reported stemmed from accusations he broke into two homes to steal prescription pills. It wasn't the smoothest stay. Leaf was in a drug treatment center but got kicked out and returned to traditional prison after violating the conditions of his placement, including, according to an administrator, "threatening a staff member."

And while he was in prison in Montana, he also got in trouble in Texas because the arrest violated his probation there. In Texas, he had pleaded guilty to seven counts of obtaining a controlled substance by fraud after a mess that included accusations he broke into a player's home while he coached at West Texas A&M and used an incomplete medical history to get nearly 1,000 pain pills, the Associated Press reported. A Texas judge sentenced Leaf to five years in prison—but he isn't expected to go to serve it there because of credit for his time served back in Montana.

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So after all that mess Leaf is free, although out on parole.

Image via Montana Department of Corrections