Former NFL quarterback Ryan Leaf, considered to be one of the biggest busts in football history, was arrested in Montana on Monday for the second time in three days for burglary, theft, and criminal possession of dangerous drugs.

Leaf, the former No. 2 draft pick by the San Diego Chargers, was arrested on Friday after a month long investigation that determined he was robbing homes for prescription pills. After posting $76,000 bail on Friday, Leaf allegedly went out on Saturday afternoon for another burglary run with intent to acquire prescription pills.

Bail has been set at $101,000 for the most recent charges, but due to a probation violation he cannot be released from jail, a police spokesman told the Associated Press. He was arrested in 2009 for stealing nearly 1,000 prescription pills from Texas pharmacies and agreed to 10 years of probation in a plea agreement.

The latest charges represent a new rock bottom for a player that had claimed he had turned the corner for the better just a short time ago. After the plea agreement in 2009, Leaf claimed that therapy helped him get past his failed career as a NFL player and prepared him well for the future.

He underwent surgery last year to remove a benign brain tumor, but it apparently did not deter him from returning to a life of crime.