The Amagansett Press lawsuit trail run by YouTuber Jason Gutterman includes one paid settlement in Silverthorne, Colorado; an active federal civil rights case in the Northern District of Florida arising from a 2021 arrest in Bay County; and a pre-suit demand sent to the City of Sedona, Arizona in May 2026. As of mid-2026, only one of the three has produced money, and only one claim against one officer remains alive in the Florida litigation.
Silverthorne, Colorado: $9,500 Paid
The Silverthorne matter is the only resolved case with a payout. After a February 24, 2020 confrontation at the town’s post office, where Gutterman filmed P.O. boxes and bulletin boards and police eventually ordered him to leave, he threatened suit. The town paid $9,500 rather than defend a federal case.1Summit Daily News. Silverthorne Pays $9,500 Settlement to First Amendment Auditor Following Incident at Post Office
Silverthorne Police Chief John Minor said the settlement was purely an economic decision and not an admission of wrongdoing, and that his department stood behind its officers. He told reporters that litigating at the federal level would have been “much costlier” than the payout.2Free Speech Project, Georgetown University. Colorado Town Pays $9,500 to First Amendment Auditor Following Post Office Confrontation
Bay County, Florida: Active Federal Case
The Florida lawsuit is the one still in court. On November 9, 2021, Bay County Sheriff’s Office Sgt. Ralph Grainger arrested Gutterman outside the UPS Customer Center on Minnesota Avenue in Lynn Haven, across from Mosley High School. The cited charge was Florida Statute 810.0975, which restricts being within 500 feet of a school without a “legitimate purpose.” His 17-year-old son was handcuffed but never booked. Gutterman spent two days in jail, and a Bay County judge dismissed the charge on November 12, 2021.3Panama City News Herald. Bay County Florida Sheriffs Deputies Arrest Journalist
Sheriff Tommy Ford defended the arrest in a news release and said the deputies involved would receive additional training on constitutional policing.3Panama City News Herald. Bay County Florida Sheriffs Deputies Arrest Journalist Attorney Kevin Alvarez sent a formal notice of intent to sue in April 2022, alleging battery, false imprisonment, false arrest, malicious prosecution, First Amendment retaliation, defamation, and deliberate indifference against the sheriff’s office, the City of Lynn Haven, and the Florida Department of Financial Services.4myPanhandle.com. YouTuber Files Lawsuit Notice With Bay Co. Sheriff
What Was Filed
Jason and Benjamin Gutterman filed Gutterman et al v. City of Lynn Haven Florida et al, Case No. 5:25-cv-00230, in the Northern District of Florida on September 1, 2025, under 42 U.S.C. § 1983. The individual defendants were:
- From the Bay County Sheriff’s Office: Sgt. Ralph Grainger and deputies Austin Crosby, Michael Ruthven, and Derrick Swann.
- From the Lynn Haven Police Department: officers Josh Newsom and John Sumerall.
Sheriff Tommy Ford and the City of Lynn Haven were also named initially. Both were terminated from the case on February 26, 2026, with no recorded monetary settlement tied to their removal.5PACER Monitor. Gutterman et al v. City of Lynn Haven Florida et al
Where It Stands
On June 3, 2026, Chief Judge Allen C. Winsor ruled on a group of motions to dismiss. The court dismissed the claims against Newsom, Ruthven, Crosby, Swann, and Sumerall. It granted in part and denied in part the motion filed by Sgt. Grainger, leaving at least one claim alive against the deputy who initiated the arrest. Grainger was ordered to answer the surviving claim by June 17, 2026, and the case remains in active litigation.5PACER Monitor. Gutterman et al v. City of Lynn Haven Florida et al
Sedona, Arizona: Pre-Suit Demand
Sedona is not yet a lawsuit. On April 8, 2026, Jason and Ben Gutterman were filming storefronts from a public sidewalk along State Route 89A in Uptown Sedona when Jesse Alexander, described as COO of the adjacent Sinagua Plaza, told them to leave. Sedona Officer Steven Willadsen, after a brief phone conversation with Police Chief Stephanie Foley, issued a formal trespass warning. According to the Guttermans’ attorney, Willadsen attributed the theory that the sidewalk was private property to Deputy City Manager J. Andy Dickey.6Sedona Red Rock News. Pre-Suit Demand and Notice of Intent to File
On May 1, 2026, San Antonio attorney Brandon J. Grable sent the City of Sedona a pre-suit demand letter seeking $25,000 for each client, a written apology, revocation of the trespass warning, and mandatory third-party First Amendment training for city employees. The letter warned that if the city did not respond substantively within 45 days, the Guttermans would file suit under 42 U.S.C. § 1983 in the U.S. District Court for the District of Arizona. The city said the claim was under review with the City Attorney’s Office, and no lawsuit had been filed as of early May 2026.7Sedona Red Rock News. Lawyer Alleges Constitutional Violation for Uptown Incident on April 8, Demands $50K
Why These Cases Tend to Settle
First Amendment auditors across the country routinely file civil rights suits under Section 1983 after being arrested or told to stop filming, and many end in settlements or dismissed charges. Federal appeals courts have recognized a right to record officials performing public duties, though the U.S. Supreme Court has not ruled directly on the question.8UNC School of Government. First Amendment Audits
For small-town governments, the math often favors payment. The Silverthorne outcome is the clearest example: officials publicly maintained their officers had done nothing wrong, then wrote a $9,500 check because federal defense costs would run higher. That economic pressure gives auditors leverage independent of how the underlying legal questions would be resolved at trial.9DuPage County Bar Association. First Amendment Audits