BANGOR, Maine — Jack Dempsey Bailey II was convicted Monday for the second time of sexually assaulting two friends of his daughter’s in Bangor between 2003 and 2005.
Bailey, originally convicted a year ago, was granted a new trial in March by the Maine Supreme Judicial Court. Instead, he chose to plead guilty and take his case to the state’s high court again.
His plea, entered Monday at the Penobscot Judicial Center, is conditional and would allow Bailey, 48, of Bangor to appeal the denial of a motion to suppress evidence to the Maine Supreme Judicial Court again while he remains incarcerated.
If Bailey were to win the second appeal, the charges against him would be dismissed. If the state’s high court were to reject the appeal, a plea agreement with the Penobscot County District Attorney’s Office calls for Bailey to be sentenced to 20 years in prison with all but eight years suspended — two years less than the current sentence he is serving at the Maine State Prison in Warren.
Bailey, the former owner of a Bangor restaurant, first was convicted in January 2009 after a jury-waived trial on 10 counts of gross sexual assault, one count of sexual exploitation of a minor and two counts of unlawful sexual contact.
A month later, Superior Court Justice William Anderson sentenced Bailey to 20 years in prison with 10 years suspended for repeatedly having sex with one girl when she was between the ages of 11 and 13, inappropriately touching a second girl, and videotaping a victim exposing herself to the camera.
In March, the Maine Supreme Judicial Court unanimously overturned that conviction because evidence was obtained illegally. The case was sent back to Penobscot County.
Last month, Anderson threw out evidence illegally obtained from Bailey’s computer and the videotapes of Bailey’s victims found as a result of the computer search. Anderson, however, ruled that the victims could testify.
Defense attorney F. David Walker IV of Bangor said Monday that he would appeal that decision and argue that the identity of the victims is “fruit of the poisonous tree,” meaning it should be excluded because police would not have been able to identify them except for the illegal search of Bailey’s computer.
Michael Roberts, deputy district attorney for Penobscot County, said he does not believe the appeal will be successful because the victims could have come forward on their own without the search of Bailey’s computer.
As part of the second plea agreement, the sexual exploitation charge was dismissed Monday. Bailey pleaded guilty to the other 12 charges.