John Looney, Sr., owner of Bad Boy Bail Bonds, speak to the
A Montana bail bondsman who has filed a lawsuit in federal court alleging that two Bozeman Municipal Court judges unfairly and illegally targeted his business by refusing to honor his company’s bonds has filed a new lawsuit in state court alleging that the two judges are threatening his business again, despite a federal court injunction.
In a pattern described in court documents filed in Gallatin County on Tuesday, Bad Boy Bail Bonds, a company owned and operated by John Looney, Sr., received two notices from the Bozeman Municipal Court that demand two bail bonds that have been forfeited after the clients didn’t show up for their respective court hearings. However, Looney was not a part of the business then, and only purchased the name later, but did not buy the bail bonding business, which remained in Helena.
A similar legal stand-off occurred last year when the Bozeman Municipal Court ordered Looney and his bail bonding business to pay a different forfeited bond, which he challenged. In all circumstances, Looney has brought documentation to prove that he wasn’t an owner in the original business, did not issue the bail bonds, and had only purchased the name, after all three bonds were issued by Bad Boy Bail Bonds, which was then owned by Willoughby Insurance.
Despite his defense, the two municipal court judges — Karolina Tierney and J. Colleen Herrington — ordered Gallatin County Officials not to accept any bail bonds from Looney. They also filed a complaint with the Commissioner of Securities and Industry to have his bail bonding license revoked, something that did not happen. With the threat of suspending his bail bonds at one point, Looney’s bonds were also not being honored in other counties, risking that his business would have to close.
In the meantime, Looney filed a complaint with the Judicial Standards Commission, the state’s oversight body charged with disciplining judges based on complaints. After Looney filed the complaint, the judges said they would not honor his company’s bonds until withdrawing the complaint, according to court documents.
Looney then took the matter to federal court, where a case against the judges is still being litigated. On Oct. 25, 2024, federal judge Donald W. Molloy ordered that Bozeman Municipal Court immediately reinstate Looney’s bonding privileges.
Tuesday’s court filing now means that Looney will have a state and a federal case against the two sitting judges for abusing their power.
“Despite the injunction, (the judges) have resumed their retaliatory actions and are again seeking to impose liability on Mr. Looney for forfeitures of bonds issued by other individuals — bonds that he had no involvement with and for which he has no liability,” documents in the new case state.
Two more bonds at issue
The latest case concerns two bail bonds, both issued by Bad Boy Bail Bonds when it was owned by Willoughby Insurance. The first was a $1,420 bond amount issued on Oct. 28, 2018, by bail agent Verda Shingleton to Kevin Flores.
On April 16, 2020, John Willoughby, owner of Willoughby Insurance, executed a $1,060 bond for Gabriel Lopez, on a general contempt charge. When Lopez failed to appear, the court issued a notice of forfeiture on Sept. 22, 2021.
However, Looney did not purchase the name until December 2022, more than a year later. Then, according to court documents submitted as part of the case, he was only purchasing the name and a telephone number, but not the bail business, assets or the related insurance.
But, on Jan. 23, 2025, Looney received two letters from the clerk of the Bozeman Municipal Court demanding those bond forfeitures, one of them nearly six years old, within 30 and 20 days respectively.
Looney’s attorney, Bozeman-based Matthew Monforton, said his client is concerned that if the court enters a judgment against his bonding it could result in halting his ability to write bail bonds, or they will try to seize assets.
“The Bozeman Municipal judges’ obsession with saddling Looney with forfeitures from other bail bondsmen demonstrates that they want payback, not justice,” Monforton said. “The Montana Legislature and the Judicial Standards Commission refuse to rein in the Bozeman Municipal judges, so once again, John is having to fight on his own.”