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Clearwater picks home-grown police chief in Tony Holloway

CLEARWATER — This city's next police chief first made a name for himself by selling crack cocaine on street corners while dressed in a sweat suit, sneakers and gaudy gold jewelry.

During the crack boom of the late 1980s, residents of Clearwater's rough-and-tumble North Greenwood area complained that cops were busting the black dealers but not the mostly white buyers who were cruising into their neighborhood.

So Officer Tony Holloway worked nights undercover, busting buyers with reverse stings. The neighbors could have sandbagged him by pointing out he was a cop, but instead they dragged lawn chairs onto their porches to watch him work.

"It was crazy," he once recalled.

Holloway, 47, was named Clearwater's next police chief Monday. He will succeed Sid Klein, a semi-legendary figure who retires next month after nearly three decades as chief.

During his nearly 22-year career in Clearwater, Holloway rose through the ranks to become the city's first black police captain. He left in 2007 to become chief in Somerville, Mass., an ethnically diverse city outside Boston. Its population is 77,000, compared with Clearwater's roughly 108,000.

City Manager Bill Horne, who picked Holloway from a field of more than 100 applicants, felt he was the most qualified and that his knowledge of the city was a significant advantage.

"We need a chief who is personable and approachable, but who can make the tough decision," Horne said Monday. "I think he will bring fresh ideas and make whatever changes are appropriate to build upon what Sid Klein has created."

Holloway started out as a Clearwater patrol officer in 1986. He worked the suburban streets of Countryside and the tourist hot spot of Clearwater Beach before being assigned to fight drugs in North Greenwood.

Around that time, a group of black officers met with Klein to talk about promotion opportunities. They felt they weren't part of a clique of officers who got promoted. Klein told them to go back to school to boost their qualifications.

"He wasn't going to lower the bar," Holloway recalled.

As Holloway climbed the ranks, he worked in every division except internal affairs. He was part of a community policing program. Then he supervised theft and fraud detectives. Then he oversaw all the patrol officers on the city's west side.

Colleagues and community leaders praised him for his calm demeanor and his problem-solving approach to police work.

He earned a business management degree from Eckerd College and later got his MBA. Klein saw potential in him and assigned him to work on budgets and other pencil-pushing administrative duties to broaden his understanding of law enforcement.

Now, as Clearwater's chief, Holloway will earn $119,000 a year plus benefits. The city wants him in place by the time Klein retires Feb. 26.

Holloway couldn't be reached Monday evening because he was traveling.

Holloway is married to Clearwater lawyer Andra Dreyfus. They have no children. Dreyfus remained in Clearwater when Holloway moved to Massachusetts, so the couple made do with a lot of weekend visits.

As Clearwater narrowed down its search for a chief over the past few months, political observers had considered Holloway the front-runner to get the job.

"I knew people would see him as a 'favorite son' candidate," Horne said. "But I have tried to be open-minded all the way though this."

Holloway impressed residents at a public forum last month. And City Council members expressed support for the pick Monday.

"I think Tony has a lot of corporate knowledge of Clearwater. He knows all the players, so I think that will be a real benefit to him," Mayor Frank Hibbard said. "He's gained some good experience up in Massachusetts, so I look forward to seeing how he's going to do in filling Chief Klein's shoes."

Growing up in Tampa, Holloway nearly became a firefighter or joined the military.

But there was this police officer he kept running into. The officer worked off-duty on weekends at a McDonald's where Holloway and his friends hung out.

The officer was always friendly. He listened to the young men and gave them advice. He'd ask if their plans for the night would land them in trouble.

That's what inspired Holloway to give police work a try.

"Does race play an important part of it? No, not really," Holloway once said of his ascension to the top.

"We all wear the same uniform, and the color is blue."

Mike Brassfield can be reached at or (727) 445-4160.

Clearwater picks home-grown police chief in Tony Holloway 01/11/10 [Last modified: Monday, January 11, 2010 11:14pm]
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