Key West police and city code officers arrested multiple people Wednesday night on Duval Street for not wearing masks, then obstructing justice by refusing to sign the citation or striking the officer.

When the Keys Weekly requested arrest information for all mask violations from Wednesday evening, Key West police spokeswoman Alyson Crean provided information about two female suspects who were taken to jail after their encounters with officers about masks escalated. However, further investigation by Keys Weekly revealed at least one additional arrest that also stemmed from a mask violation. 

“Officers can’t take people to jail just for not wearing a mask,” Crean told Keys Weekly on Thursday. “The officer warns them, then offers them a mask, and if they still refuse to wear one, they’re cited. When people refuse to sign or accept the citation, or when the situation escalates somehow, that’s when a person is arrested.”

Crean said officers took two women to jail Wednesday night for mask violations in separate incidents that had escalated. The female suspects are facing charges of battery for allegedly striking a code compliance officer in the shoulder as well as obstruction of justice for refusing to accept the citation.

Further investigation revealed a fire commissioner from Palm Harbor, Florida was arrested near the intersection of Duval and Caroline streets in an incident that started with a mask warning.

James Dalrymple, 64, is seen in a friend’s YouTube video being arrested for obstruction of justice. A Key West police officer is heard telling the man that he had refused to wear a mask. When Dalrymple said he didn’t have a mask, the officer says he offered him a mask and Dalrymple refused to wear it. The officer then says that Dalrymple was under arrest for obstruction of justice by refusing to identify himself to a law enforcement officer. Dalrymple then told the officer that his wife had his ID.

Dalrymple’s friend, Kim Adams, who filmed and posted the video, is heard repeatedly saying, “But we’re outside. You’re getting arrested for not wearing a mask outside?”

“He is sitting in a jail cell right now and all he was doing was walking outside without a mask on,” Adams wrote in the video description on YouTube.

A fourth arrest early Thursday morning may also have been mask-related, but Keys Weekly is awaiting confirmation from the sheriff’s office or police department.

When asked whether the city’s increased enforcement of its mask mandate was related to heightened COVID sensitivities surrounding the passing of Cheryl Cates early on Wednesday, Dec. 2, Crean said the two were unrelated.

“This was not related to the passing of Cheryl Cates,” Crean said. “As we’ve gotten busier, we’ve stepped up enforcement. Officers handed out 20 masks [Wednesday] night and issued several citations that did not end in arrest. If someone refuses to accept the citation, that’s an arrestable offense.” 

Editor’s Note: Out of respect to the Cates family and their privacy, this is the Keys Weekly’s first reference to the tragic passing of Cheryl Cates. This decision was only made after the Cates family issued an official statement earlier on Thursday,  Dec. 3. Any additional Keys Weekly coverage relating to the Cates family will continue to be based solely on official statements or releases from the family.

Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.