MAN ALERTS TO PRESENCE OF UNDERCOVER OFFICERS BRADENTON - Jeffrey Gutierrez just couldn't keep quiet one evening when he saw undercover police hanging around in his neighborhood. "That's the police! That's the police!" Gutierrez yelled, pointing to the plainclothes officers in a truck. He was right, and the police were not amused. Officers in a marked police car showed up a few minutes later and hauled Gutierrez to jail on the misdemeanor charge of obstruction of justice. But state prosecutors dropped the case within weeks, saying the Bradenton man had a free speech right to tell the whole neighborhood about the presence of the undercover officers, so long as the man wasn't a lookout for the drug dealers on the corner or otherwise conspiring with them. He wasn't. The case highlights the long-standing clash between free speech rights and the clandestine nature of some police investigations. Undercover narcotics detectives are supposed to be the most invisible officers on the force. They wear black hoods when they make an arrest. Unlike other officers, their names and job descriptions are not public record. Blowing an officer's cover could ruin a case and potentially get him killed. But prosecutors and Florida appellate courts say that free speech includes the right to disclose an undercover officer's identity. Bradenton Police Chief Michael Radzilowski said in an interview that his department will continue to arrest residents who interfere and therefore jeopardize an undercover officer's investigation. "That's obstruction," Radzilowski said after a reporter read details from the Gutierrez case. "To say it's not is absurd." Prosecutors sympathize with the police, but say their hands are tied. The state isn't going to take to trial a case it can't win. "It's frustrating for the police, sure," said assistant state attorney Donald Hartery Jr., a misdemeanor case supervisor in Manatee County who is familiar with the Gutierrez case. "If cops were never allowed to disguise themselves as not cops, you'd never be able to make vice busts." Police know the Gutierrez name. Manatee County court records show that Jeffrey Gutierrez, 25, was arrested in October 2002 on obstruction charges after he chased a police cruiser on his bike and yelled at two officers. When he refused to get out of the road, an officer yanked him off the bike, put him on the ground and handcuffed him. Gutierrez was upset that his brother, brother, George, was being taken away for obstruction after refusing to cooperate in a domestic battery investigation. A police dog bit and injured Gutierrez's brother after he ran from the police. Jeffrey Gutierrez took a plea deal in that obstruction case. A year later, he was sentenced to six months of probation for marijuana possession. On March 18, Jeffrey Gutierrez happened upon a typical Friday night narcotics sting. Several undercover officers were posing as street dealers and users, selling and buying crack cocaine on 10th Avenue East in Bradenton, an area marred by frequent drug sales. Their undercover truck was equipped with video and audio equipment to monitor deals, like the one going down at about 6:30 p.m. in the 400 block of 10th Avenue. An undercover detective asked a man for $20 worth of rock cocaine. The officer got what he asked for. Police arrested two people. After the bust, Gutierrez, who has lived in the neighborhood and has relatives there, pulled up behind the undercover truck. He honked his horn, pointed at the vehicle and shouted to people on the street. "That's the police!" he shouted at least twice. When Gutierrez pulled away, an officer in a marked car stopped him. He was charged with obstruction of justice. A police lieutenant said the man's shouting scared off suspected narcotics dealers. But 10 people were charged that night with drug possession and sale crimes, a sweep that suggests Gutierrez's words didn't destroy the planned narcotics operation. Police put out a news release March 19. That morning, a judge said at a court hearing that there was no probable cause to justify the Gutierrez arrest - at least not based on the limited details of the Bradenton police report. State prosecutors dropped the case. Hartery, the prosecutor, said in a recent interview that because Gutierrez had nothing to do with the drug dealers on the evening of March 18, he did not hinder the police investigation. If he had interfered when the police were arresting a suspect, the obstruction charge would have been warranted, Hartery said. But the police were not in the middle of questioning or arresting anyone when they encountered Gutierrez. The officers were just driving around looking to buy and sell drugs. Chief Radzilowski isn't the only one who questions the obstruction law as it applies to disclosing the identity of an undercover officer. Judge Frank A. Shepherd of the Third District Court of Appeal in Miami has said free speech rights do not apply when a person tries to thwart an ongoing undercover operation. "No one yells '99 police' to signal that the ice cream is coming," Shepherd said in an opinion in an obstruction case last year. "Forecasting '99 police' is meant to alert ... so that any illegal acts can quickly come to a close, evidence can be flushed and law enforcement can be frustrated." There's a difference, the judge said, between someone who rants and raves about the presence of the police to thwart an undercover operation and the person who questions or criticizes the police. Undercover officers are asked all the time whether they are cops. "You are always going to argue with them. You play it off. 'Hey, I ain't no police,' " said a former undercover officer with the Bradenton Police Department. Sometimes, the street dealers who were busted by undercover police will later watch officers sell and buy drugs in the neighborhood without saying a word. Some dealers don't want any more trouble, so they keep their mouths shut.