First, his company, Tamarack Resort, filed for bankruptcy protection earlier this year after it announced it was more than $300 million in debt and a planned $118 million loan from French bank Societe Generale fell through.
The move was an attempt to dodge Credit Suisse, to which Tamarack owes more than $262 million. The bank has since asked that the courts allow them to foreclose the resort to recoup their money.
Then, there's the March 28 arrest for allegedly hitting a parked car in Boise and leaving the scene of the accident without reporting it.
The hit and run happened in September 2007 in downtown, when witnesses reportedly saw Boespflug check out the damage to his car and then took off.
Boespflug bonded out of jail in Cascade with $300 cash, but we're guessing he'll be spending some more quality time in the courtroom soon.