Jasinski pleaded guilty to possession of oxycodone with attempt to distribute and failing to file a tax return for 2008 (the year he competed on Big Brother and won the ninth season's $500,000 grand prize) in U.S. District Court in Boston on Monday, The Associated Press reported.
Jasinski was immediately handcuffed and taken into custody, however his sentencing will reportedly not take place until January 11.
While Judge William Young said Jasinski faces up to 14 years in prison for the drug charge and a maximum of one year for the misdemeanor tax charge, it is not clear what sentence prosecutors will recommend. Valerie Carter, Jasinski's lawyer, reportedly said she plans to request a house arrest sentence.
Carter also requested Jasinski be allowed to remain free on bail until his sentencing, however Young ordered he be taken into custody.
Jasinski, a 32-year-old from Delray Beach, FL, was arrested in October 2009 after he flew into Boston and attempted to sell 2,000 oxycodone pills to a Drug Enforcement Administration witness.
According to prosecutors, the witness -- who had made a prior buy of 2,000 oxycodone pills from Jasinski in February but been arrested earlier in October -- met Jasinski at Logan International Airport on October 17 and then drove to a North Reading, MA strip mall where DEA agents arrested Jasinski after he pulled the pills from a sock stuffed in his pants.
The witness set up the drug buy via an October 8 phone call to Jasinski, according to a DEA affidavit filed at the time of the Big Brother winner's arrest.
After his arrest, Jasinski allegedly told DEA agents he had used his Big Brother cash prize to bankroll his drug dealing and boasted he had been "obtaining thousands of pills of oxycodone" which he'd sold "to customers all along the East Coast."
Jasinski subsequently pleaded not guilty and challenged the DEA claims, saying he had no memory of making the statements after his arrest -- which his lawyer alleged involved "entrapment and outrageous government conduct."
He then remained in jail until mid-December, when he was sent to an Westboro, MA substance abuse treatment center after being released on $200,000 bond which was secured by his parents' home and three Florida properties.
Jasinski remained at the in-patient center for four months, when he moved to an out-patient treatment center near his parents' home in New Jersey, according to Carter.
Shortly thereafter, prosecutors also indictedMatt McDonald -- a Charlestown, MA resident who had been a close ally of Jasinski's on Big Brother's ninth season -- on a conspiracy to distribute oxycodone charge for allegedly being part of Jasinski's drug ring.
Prior to entering his guilty pleas on Monday, Jasinski reportedly told Young he is being treated for drug addiction and bipolar disorder.
"I'm actually seeing results," he said, according to The AP.