By Terrence McCoy
By Allie Conti
By Chuck Strouse
By Scott Fishman
By Terrence McCoy
By Ryan Yousefi
By Ciara LaVelle, Kat Bein, Carolina Del Busto, and Liz Tracy
By Pepe Billete
7. Now it's time for some R&R and a cool one, not unlike those hard-working Company men who, after a tough day at the office plotting Fidel's downfall, needed a place to unwind -- somewhere they could loosen their skinny ties and not have to worry about whether their shoulder holsters were showing, where they could toss back a few and shoot the bull without fear of spilling secrets into the wrong ear. Drinking -- with other CIA people, of course, for security's sake -- was one of the only social safety valves available to those sealed off in the high-pressure world of JM/WAVE, and certain bars were adopted as unofficial Agency hangouts. The Stuft Shirt Lounge in the former Holiday Inn on Brickell was one, as was Alabama Jack's on Card Sound Road, with its raffish clientele and convenient location on the way back from paramilitary bases in the Keys. But the greatest of all the spy dives may have been the Big Daddy's at SW 27th Avenue and Bird Avenue, widely known from its location as the "27 Birds." Agents liked the bar's cool, secret-code-sounding nickname, and they appreciated its anonymity and darkness-at-noon atmosphere. "It had no windows and it was pitch black inside, and they had live rock and roll," remembers Jimmy Flanigan, son of original "Big Daddy" Joe Flanigan and the man responsible for its current kinder, gentler incarnation as Flanigan's Laughing Loggerhead Seafood Bar and Grill. "There were these purple velvet couches -- people used to sink down in them. It was where the Grove-ites met the motorcycle gangs and the DEA met the smugglers. And somehow everybody got along." Flanigan's memories of the old 27 Birds come from his childhood, a few years after Miami's Sixties spook heyday; in his mind, the bar's CIA pioneers have ascended to the status of legend, up there with "the really notorious bad guys [who] are all dead now." His place is probably too respectable for them today -- unless, of course, they happen to be looking for somewhere to bring their grandchildren.
8. Next stop is Brickell Avenue near downtown. The building that once stood at 600 Brickell housed the offices of Paul Helliwell, a prominent Miami attorney and veteran of the OSS, the CIA's World War II predecessor. Helliwell's place of business was also where the phone rang if anyone dialed the number for "Red Sunset Enterprises" -- an Agency front company set up to recruit frogmen and other boom-and-bang experts for Operation Mongoose. Red Sunset was typical of the more than 50 dummy corporations created by the CIA in Dade to conceal its anti-Castro activities. "What the CIA did, in many cases, they would cut a deal with an attorney who would essentially serve as a point to receive phone calls and also mail drops," says Soldier of Fortune magazine editor Robert K. Brown, a sardonic observer of South Florida's early-Sixties cloak-and-dagger scene. "If some of their personnel got in trouble, there was an address they could give, and there would be a dedicated phone line so that if you called in on this number, the number would be answered with the corporate name of the cover." Brown and his buddy Marty Casey hung around the edges of the paramilitary circus, gathering material for a never-to-be-published book called Ripped Cloak, Rusted Dagger. Their research tended toward the mischievous, including a nighttime foray into the JM/WAVE compound and weekend raids on the trash cans of CIA front companies. One day, just for grins, they decided to check out Red Sunset. Walking into Helliwell's posh office suite without calling ahead, they announced that they were former members of a navy underwater demolition team looking for work. Without batting an eye, the receptionist handed them employment applications, which they proceeded to fill out using false identities. Casey remembers that Brown used the name "Ernst Blofeld" -- the fictional nemesis of superspy James Bond.
9. Walk a couple of blocks up the street to the Brickell Bridge and behold the murky Miami River. Not long after he started work at the Merrill Stevens boat yard in 1960, Fred Kirtland noticed a dramatic and unusual sales trend. "Almost any kind of vessel that was near seaworthy was being purchased by the Cubans with a hell of a lot of CIA money to go down there [to Cuba]," says Kirtland, who would later become president of Merrill Stevens. The months leading up to the Bay of Pigs marked the beginning of a wild and heady time for everybody along the Miami River, as obviously warlike craft with powerful engines, gun mounts, mysterious antennae, and battleship-gray paint proliferated. The crew of one patrol boat didn't even bother to conceal the 50-caliber machine guns mounted on its stern when they tied up under the Flagler Street bridge; reportedly, it and other vessels of the "Cuban Revolutionary Navy" were regularly pointed out to tourists on sightseeing boats. The Agency itself was constantly patrolling the downtown area with two radio-eavesdropping boats, the Dart and the Barb, in an effort to intercept signals from Castro agents in Miami. Meanwhile, according to Kirtland, riverside boat yards were experiencing a war boom. "To the best of my knowledge, any work done on any of the boats that they used was done by existing yards on the Miami River," he says. "There was Miami Ship, Tommy's Boatyard, Merrill Stevens, Jones Boatyard.... A lot of these yacht places that do some commercial work were involved." According to Kirtland, after the Bay of Pigs disaster, the CIA's operational presence along the river became much less visible but continued nonetheless. He remembers hearing about work being done for a company called Transworld Marine, linked to a man named Gordon Campbell. (Campbell was JM/WAVE's maritime operations chief and lived, appropriately enough, on a boat at the Dinner Key Marina.) "I think it was fairly common knowledge when you'd find people out to buy fast boats, what it was for," he says. "Transworld Marine purchased boats, new construction out of New Orleans, that were used for follow-up operations. Gordon Campbell, if my memory serves me correctly, purchased one out of New Orleans. Name of the boat was Cutlass. That boat stayed around well after the Bay of Pigs."