On Tuesday, February 18, 2025, the Daily Montanan reported that a Montana bail bondsman, John Looney, Sr., initiated a new lawsuit in state court against two judges from the Bozeman Municipal Court. This legal action comes despite an ongoing federal lawsuit where Looney alleges that the judges have unfairly targeted his business by refusing to recognize his company’s bonds.
Looney operates Bad Boy Bail Bonds, a company that he acquired under its current name after the original business, which remained in Helena, was owned by Willoughby Insurance. The conflict began when Looney received two notices from the Bozeman Municipal Court demanding payment for bail bonds that had been forfeited due to clients failing to appear for their court hearings. However, Looney contends that he was not involved with the business at the time the bonds were issued, as he purchased the business name only in December 2022, well after the bonds were executed.
In a previous legal confrontation, Looney challenged the court’s demand for the payment of a different forfeited bond from last year. He has consistently submitted documentation proving that he was not an owner of the original business or involved in issuing any of the bonds. Despite this, judges Karolina Tierney and J. Colleen Herrington ordered county officials to refuse acceptance of any bail bonds from Looney and even filed a complaint aimed at revoking his bail bonding license, which ultimately did not occur.
Amidst these challenges, Looney filed a complaint with the Judicial Standards Commission, tasked with overseeing judicial conduct. Following this complaint, the judges indicated they would not honor Looney’s bonds until he withdrew his grievance, according to court documents. In response, Looney escalated the matter to federal court, where he is still pursuing a case against the judges.
On October 25, 2024, federal Judge Donald W. Molloy ruled that the Bozeman Municipal Court must immediately restore Looney’s bonding privileges. However, Looney’s recent state court filing indicates ongoing issues, with the judges allegedly continuing retaliatory actions against him despite the federal injunction.
The latest case involves two specific bail bonds issued by Bad Boy Bail Bonds while it was still owned by Willoughby Insurance. The first bond was for $1,420, issued on October 28, 2018, to Kevin Flores by bail agent Verda Shingleton. The second was a $1,060 bond executed on April 16, 2020, for Gabriel Lopez, who faced a general contempt charge. When Lopez failed to appear in court, the court issued a forfeiture notice on September 22, 2021.
Looney did not acquire the business name until over a year after these bonds were issued, and according to court documents, he only purchased the name and a phone number, not the original business or its assets. Recently, on January 23, 2025, Looney received letters from the Bozeman Municipal Court demanding payment for the forfeited bonds, with deadlines of 30 and 20 days respectively.
Looney’s attorney, Matthew Monforton, expressed concern that a judgment against Looney could jeopardize his ability to write bail bonds or lead to asset seizures. He characterized the actions of the judges as an obsession with holding Looney accountable for forfeitures tied to the previous bail bondsmen, suggesting that their motivations are more personal than judicial.
Source: Daily Montanan
