St. Augustine brags that it's the oldest city in America, but Pensacola is older. Spanish explorers settled there in 1559, six years before St. Augustine was founded.
But in 1561 a hurricane blew Pensacola off the map. The survivors were so discouraged they went home, and no one settled there again for a century.
The havoc wrought early Thursday by Hurricane Ivan marks another milestone in Pensacola's turbulent history, times marked by political shenanigans, repeated bloodshed and the frequent need to rebuild the town.
On a map, Florida resembles a handgun, with Pensacola at the end of the barrel. Its homegrown celebrities include boxer Roy Jones Jr. and football stars Emmitt Smith and Derrick Brooks. The economy depends largely on tourism and the Pensacola Naval Air Station.
Pensacola's nickname is "the City of Five Flags," because for 200 years the Spanish, French and British armies fought over it until Andrew Jackson unfurled the Stars and Stripes over the town (the fifth flag belongs to the Confederacy).
In 1719, a French expert reported that it was the only place in the Gulf of Mexico "in which ships can be safe from all winds."
As various armies battled to possess this treasure, they either razed or blew up the settlement. At one point, when the Spanish tried building a new fort on the beach, a hurricane wiped them out.
After Jackson invaded Pensacola and booted out the Spanish, he briefly served as territorial governor before moving on to the White House. His wife despised living in what she called a "heathen town."
Pensacola still offers plenty of sleaze - just ask former University of Alabama football coach Mike Price, fired last year amid reports he spent hundreds of dollars at a topless bar.
But what has put Pensacola on the map in recent years has been a mix of violence and religious zeal, starting in 1984. That's when four devout teenagers bombed three abortion clinics on Christmas Day as a "birthday gift for Jesus."
Then, in 1993, an antiabortion activist named Michael Griffin gunned down a Pensacola doctor who performed abortions.
The city's volatile politics spawned a string of high-profile political figures, including straight-arrow Reubin Askew.
No politician was more colorful than the wily W.D. Childers, nicknamed the "Banty Rooster," who while a state senator got funding for a football stadium for the University of West Florida even though the school has no team.
Childers survived repeated grand jury investigations, but last year he was convicted of bribing a fellow county commissioner by handing him a cookpot stuffed with cash.
Times researcher Carolyn Edds contributed to this report.
