Twenty-five-year-old Victor Gerena was to be married on September 16, 1983, but he had taken flight four days before he was to walk down the aisle. He had not become overcome with cold feet about tying the knot nor had he left his would-be bride for another woman; he had instead absconded with over $7 million after committing what was, at the time, the largest single-handed armed robbery in American history and the second-largest total armed heist.

Gerena’s avoiding apprehension has earned him a dubious distinction among those deemed the baddest of the bad: he holds the record for the longest tenure on the FBI’s Ten Most Wanted List.

Victor Gerena

The eldest of five children, Victor Gerena was born in the Bronx in 1958. His family, minus his father, moved to West Hartford, Connecticut, in 1970.

In high school, Gerena achieved good grades, played football, was a star wrestler, and served as a legislative intern at the state capital. His success, however, did not follow at the now-defunct Annhurst College, in Woodstock, Connecticut (not to be confused with Massachusetts’ Amherst College). His grades plummeted and he left before completing his first year.

Gerena’s life then stagnated, both personally and professionally; he married and divorced twice, having a daughter with each wife, and blew through a series of menial jobs.

Young Victor

In May 1982, Gerena was hired as an armed car guard for the Wells Fargo Armored Services Corporation. He was paid $4.50 an hour to transfer millions of dollars in cash to and from the company’s West Hartford depot.

Knowing Gerena did not own an automobile, his boss, twenty-five-year-old Jim McKeon, was surprised when the man he called his best worker asked if he could park a car inside the building near Bay 5 when he arrived at work on September 12, 1983. Gerena conveyed the car was loaned from a friend and he was worried about it being burglarized or damaged. Employees parking their vehicles at the requested area was against company regulations, but McKeon allowed him to do so because several recent thefts had occured in the parking lot.

Gerena’s chosen venue and vehicle were suited for a much grander theft. The locale was adjacent to a vault and out-of-public view, and the car, a full-size 1973 Buick LeSabre, was equipped with a large trunk able to house ample cargo.

Gerena Becomes An Armored Car Guard

The day and evening proceeded normally, as Gerena and his partner, twenty-one-year-old Tim Girard, made their scheduled rounds in Hartford and Bridgeport, collecting more than $3 million in currency from local banks and businesses. An additional $4 million was already in the facility’s vault.

After the men returned to the terminal shortly after 9:00, Gerena offered to check in their guns. Girard handed him his weapon.  They and McKeon were the only people in the building.

As McKeon was doing paperwork at his desk, Gerena, with one hand, pointed his gun into his boss’ back as he grabbed his gun from its holster with the other. He then summoned the unarmed Girard and ordered both men onto the floor and bound their hands behind their backs, using handcuffs on McKeon and nylon twine on Girard. He then covered their mouths with duct tape, placed jackets over their heads, and injected them with a substance he said would put them to sleep, but it did not do so.

The incapacitated guards then heard Gerena opening the Bay 5 garage door and drive a vehicle into the terminal where he proceeded to load the over $7 million in cash weighing between 900-1,150 pounds into the trunk. After approximately an hour-and-a-half, he twice honked the car’s horn, likely signaling outside accomplices, and again opened the terminal bay door. Shortly thereafter, the guards heard the sound of a shotgun being loaded and Gerena and his cohorts leaving the depot.

McKeon and Girard eventually freed themselves and contacted the police.

The Armed Guard Becomes An Armed Robber

Eighteen hours later, the 1973 Buick LeSabre Gerena had asked to park at the Bay 5 door was found abandoned eight miles away in the parking lot of the Susset Chalet Inn near Hartford’s Brainerd Airport. Inside was a twelve-gauge Remington pump action shotgun and Smith & Wesson .36 revolver, but no money.

Gerena was found to have rented the vehicle from the Ugly Duckling Rent-A-Car, a non-credit locale, on August 29, fifteen days earlier. Authorities found no evidence he had bordered a flight at the airport.

Car Recovered

In November, two months after the theft, letters confirmed to have been written by Gerena were mailed to his mother, Gloria; his fiancée, Ana Soto; and her lawyer, Michael Graham. They were postmarked from Buffalo, New York, four-hundred miles west of West Hartford, Connecticut.

A search of Gerena’s apartment uncovered nothing relating to the robbery. His passport was found and seized.

Upon binding his coworkers, Gerena had apologized, saying he had nothing against them, but that he was “tired of working for someone else.” Acquaintances said he dreamed of living lavishly, something tough to do when making only slightly more than the minimum wage and being sued by both former wives for child support. At the time of the theft, he owed them approximately $3,000 and the amount rose with each passing month he did not pay them.

It appeared that Gerena had sought a short cut to the good life. Authorities initially believed he and one or a couple of other similarly disgruntled accomplices had orchestrated the theft.

The following year, however, the caper was learned to have involved multiple nefarious players having greater illicit intentions, and that Victor Gerena, despite doing all of the physical labor, was the low man in what the press dubbed “The Big Sleep Heist.”

Gerena Hoped To Live The High Life

A week-and-a-half after the robbery, a West Hartford detective was told it had been orchestrated by the Puerto Rican terrorist organization Ejército Popular Boricua (“Boricua Popular/People’s Army,)” more commonly known as Los Macheteros, (loosely translated as “Machete Wielders” or “Cane Cutters.” An extremist faction of the broader movement seeking the Commonwealth’s independence from the United States, the militant insurgent group established in 1976 had carried out several attacks against American personnel in Puerto Rico in the late 1970s and early ‘80s, including the December 1979 ambushing of a bus carrying eighteen Navy seaman, in which two were killed and ten were wounded, and the January 1981 bombing and destroying of eleven Puerto Rican National Guard jets valued at $45 million.

The claim of Macheteros involvement in the Big Sleep Heist was initially dismissed because Gerena, though of Puerto Rican dissent, had never expressed an opinion on any political issue, Puerto Rican-related or otherwise. In listening to authorized wiretaps in Macheteros safe houses in Puerto Rico and America over the following year, however, the FBI came to believe the tip was legitimate as they heard group members talking of acquiring over $7 million in cash.

Confirmation came nearly a year after the armed robbery.

A Los Macheteros Logo

On September 9, 1984, the Hartford Courant received a postcard signed Victor Manuel Gerena Ortiz in which the now FBI Ten Most Wanted fugitive confirmed his affiliation to the Macheteros and conveyed that an explanation of what happened to the stolen money would soon be forthcoming. The card featured the Statue of Liberty as a symbol for Puerto Rican independence.

Over the following month, the San Juan, Puerto Rico, headquarters of the Associated Press and Agencia EFE, the major Spanish-language international news agency, received three similar postcards criticizing United States intervention in Latin America. Postmarked September 9 from New York City, one had a similar image of the Statue of Liberty, one showed another shot from the Big Apple, and another had a scene from New Hampshire.

Handwriting analysis confirmed these letters were also written by Gerena. All were mailed in envelopes postmarked New York City.

One Of Gerena’s Letters

On October 20, five weeks later, the San Juan UPI (United Press International) office received an anonymous phone call saying a Los Macheteros letter was at a specified bus stop in San Juan. Beneath piles of leaves and trash was a typewritten letter having Macheteros letterhead and dated the day before. The group, specifically the Los Tainos cell, boasted of committing the Wells Fargo robbery, saying it was one of several “military economic operative[s]” they had carried out against the company and by extension, the American economy and Imperialism.

The Macheteros also stated the money was in a state of maximum security and that “Comrade Gerena” was one of their members whom they had trained for the robbery for over a year before the occurrence.

Seven months later, additional Macheteros letters mailed from New York City were received by the Hartford Courant and two San Juan newspapers. Dated April 1, 1985, the group criticized a Hartford federal grand jury that had recently subpoenaed local Puerto Rican independence advocates in the robbery investigation.

Each letter contained one-half of a $10 bill which was confirmed, through serial numbers, to have been taken during the robbery.

The Macheteros Prove Their Involvement 

The Macheteros had taken credit for the October 30, 1983, bombing of an American federal building in San Juan, saying it was in retaliation to the American invasion of the island of Grenada, five days earlier. The intended target of an anti-tank LAWS (Light Anti-Armor Weapons System) rocket was the FBI office, but it was only minimally damaged; the suite of the United States Department of Agriculture bore the brunt of the blast. No one was injured.

American Federal Building

San Juan, Puerto Rico

The rocket was believed to have been purchased from a black market arms dealer with money obtained from the Wells Fargo heist seven weeks earlier. The serial number of the tube which had been left by the bomber showed it had been used by the United States in the Vietnam War. Following American withdrawal, it was either abandoned or captured by the North Vietnamese who had shipped it to communist ally Cuba.

he Macheteros had received subsequent arms, supplies, and training in Cuba, as well as support in their terrorist undertakings. The Cuban connection led many in the FBI to believe that infamous dictator Fidel Castro, who had long supported Puerto Rican independence from the United States, had at least partly financed the Macheteros, which many in the FBI believe to have been an extension of his Communist Cuban Intelligence Service.  

In addition, Macheteros cofounder and “First Comrade in Charge” Filiberto Ojeda Rios had trained as a communist agent in Cuba during the 1960s, before returning to Puerto Rico. After being arrested in 1970 for bombing a tourist hotel, he jumped bail and returned to Cuba.

Filiberto Ojeda Rios

In August 1985, coordinated FBI raids in Puerto Rico, Mexico, Texas, and Massachusetts resulted in the arrests of thirteen Macheteros in connection with the 1983 Wells Fargo robbery, including Filiberto Ojeda Rios and Juan (Junior) Segarra Palmer, another group founder. Four more arrests followed soon thereafter.

Three indicted Macheteros eluded apprehension: brothers Avelino and Noberto Gonzales Claudio, and Victor Gerena.

Numerous weapons were seized in the raids, ranging from M-16 rifles, .45 caliber Thompson machine guns, and Israeli-made Uzi submachine guns, along with hundreds of blasting caps, grenades, rolls of fuse, clocks rigged as detonators, bulletproof vests, and camouflage fatigues.

Some Of The Macheteros’ Arsenal 

Ojeda had fired at FBI agents as they raided his Luquillo, Puerto Rico home, wounding a member of the SWAT team in the eye, before surrendering. In August 1989, he was released on $1 million bond after the Supreme Court ruled his four year pretrial detention violated his right to a speedy trial even though it was his lawyers who had filed multiple motions delaying the proceedings.

The following year, Ojeda cut off his electronic bracelet and disappeared. Two years later, in May 1992, he was convicted in a Connecticut federal court of fourteen counts related to the Wells Fargo heist, including bank robbery and conspiracy. He was sentenced, in absentia, to fifty-five years in prison and fined $600,000.

Ojeda Flees

The Philips Academy and Harvard educated Juan Segarra Palmer, who had enlisted Victor Gerena for the robbery, was arrested without incident at the Dallas-Fort Worth International Airport while attempting to reenter the United States from Mexico City. He was sentenced to sixty years in federal prison in 1989 after being convicted of interfering with interstate commerce through robbery and seditious conspiracy.

Initially confined at the Federal Penitentiary in Atlanta, Segarra was later moved to a federal prison in Coleman, Florida.

Juan Segarra Palmer

In 1999, outgoing President Bill Clinton offered conditional clemency and/or early release to sixteen convicted Los Macheteros and those of the closely aligned FALN, the Spanish acronym for Puerto Rico’s clandestine Armed Forces for National Liberation, if they renounced terrorism in any continued efforts for Puerto Rican independence.

Segarra was among the fourteen members who accepted the offer. He was released from prison in 2004.

Segarra Released

On September 23, 2005, seventy-two-year-old fugitive Filiberto Ojeda Rios was tracked to a farmhouse in Hormigueros, Puerto Rico, one-hundred ten miles southwest of San Juan. Cornered again, he again began shooting. This time, he did live to tell about it.

Ojeda Killed

have fired the rocket at the Federal Building in San Juan on October 30, 1983, because his partial fingerprint was found on a nearby abandoned car. In 2008, he was found living under an alias and working as a teacher in Puerto Rico. After pleading guilty to conspiracy to commit robbery in 2010, he was sentenced to seven years in prison. He was released in February 2013 and died in July 2019.

Norberto Gonzalez Claudio was arrested on similar charges while jogging in Cayey, Puerto Rico, in 2011. The following year, he was sentenced to five years in prison followed by three years of supervised release, which he was granted in January 2015.

A third brother, Orlando, was also convicted for involvement in the robbery and has also since been released from prison.

                               

Avelino And Noberto Gonzalez Claudio

With the convictions of the Gonzalez brothers, fourteen Macheteros were found guilty on various charges in relation to the Wells Fargo robbery. One was acquitted, and the charges were dismissed against another, Anne Gassin of Boston, after she agreed to testify as a government witness against Juan Segarra, her former lover.

Only one indicted Machetero remains at large; the inside man and actual perpetrator.

Many Members Are Caught And Convicted . . .

Investigators believe the Macheteros, aided by Fidel Castro, transported, in a roundabout way, the heavily hunted Victor Gerena to Cuba where he was given sanctuary.

Through interrogations of captured Macheteros, principally Juan Segarra, information gleaned from FBI wiretaps, and interviews with Cuban agent turned defector Jorge Masetti, investigators learned that following the robbery, Ojeda and Segarra took Gerena to a West Hartford motel where they confiscated the stolen $7 million. From there, Segarra says Gerena was whisked on a Yamaha motorcycle thirty miles north to Springfield, Massachusetts, and then moved by car ninety miles northeast to Boston, where he and $2.024 million of the pilfered loot were packed into a used motor home Segarra and Ojeda had purchased with money provided by Castro.

The motor home was driven approximately 2,200 miles to Laredo, Texas, where the trio successfully crossed into Mexico, and then, escorted by Masetti and other Cuban espionage agents, driven another seven hundred miles south to Mexico City where Gerena was disguised, put up in an apartment, and given a phony Argentinian passport and papers. He and the money were then flown on Cubana de Aviacion to Cuba with the rest of the loot transported in the same manner shortly thereafter.

. . . But Gerena Is Still At Large

The letters and postcards written by Gerena and mailed from Buffalo and New York City respectively in the months after the theft appear to have been a successful attempt to throw authorities off his track, as search efforts were originally focused in the northeast as they believed Gerena was trying to cross into Canada.

Many believe the propaganda messages were written and signed by Gerena, but dictated by Ojeda and Segarra, and mailed by other Macheteros.

No, It Appears He Was Not

The substance Gerena had injected into coworkers Jim McKeon and Tim Girard was ultimately determined to have been a solution of aspirin and water. He had told them the shots would make them feel drowsy before putting them to sleep, but they had not done so. This was likely because the amount was meant for only one person.

Gerena had probably expected Girard to go home after they had completed their nightly rounds, but he had done so because several construction projects were delaying his time to and from work. The building had a small television set and he wanted to watch the Monday Night Football game between the San Diego Chargers and Kansas City Chiefs. His lingering had likely forced Gerena to dilute the dosages, causing them to fail to take effect.

(The Chargers won the game, 17-14.)

Tim Girard

The West Hartford, Connecticut, branch of the Wells Fargo Armored Services Corporation depot closed after the Big Sleep Heist.

The Robbery Led To The Depot’s Demise

At the time of the 1983 Los Macheteros-orchestrated Wells Fargo robbery, West Hartford, had a large Puerto Rican population and was a hotbed of the island’s culture and politics.

Victor Gerena’s mother Gloria was Hartford’s leading member of the Puerto Rican Socialist Party (PSSP) seeking the Commonwealth’s independence. As an “indepentista” she was aligned with Los Macheteros.Since her eldest child was little, Gloria had dragged him to numerous PSSP meetings, but he never expressed any interest in the politics.

Gloria Gerena died in 2022 at age eighty-four.

Gloria Gerena

Gerena’s fiancée, Ana Soto, also supported Puerto Rican independence. Following the robbery, she was arrested and charged with withholding information, hindering prosecution, and making false statements about the theft, specifically that she had lied about the rented Buick and several long-distance telephone calls made by her beau. All of the charges, however, were ultimately dropped after investigators concluded she had no inkling of her sweetheart’s plans to commit the robbery.

Ana received a letter from her would-be groom shortly after he is believed to have been successfully smuggled into Cuba, expressing his hope she could soon join him. The fugitive’s request to be reunited with his love was reportedly supported by Segarra but overruled by Ojeda who deemed an attempt to sneak her into the country as too risky.

Devastated by the decision, Ana, studying to be a beautician, instead turned to drugs and was imprisoned for a time.

Ana Soto

The Macheteros refer to the Big Sleep Heist as “Águila Blanca” (“White Eagle,”) the nickname of Puerto Rican revolutionary Jose Maldanado Roman, who had fought with the Cuban Liberation Army toward the end of the nineteenth century in Cuba’s quest for independence from Spain. Their code name for the heist was Pitirre III, named for a small bird known to attack larger animals.

The approximately $7.017 million stolen in the robbery is equivalent to roughly $23 million today. Approximately $80,000 believed to have been obtained from the heist was seized by the FBI during the 1985 raids in Puerto Rico and Boston. Government officials believe the Macheteros spent approximately $1 million, moved over $2 million to Cuba, and hid $4 million in safe deposit boxes, certificates of deposit, and savings accounts.

The Macheteros contend part of the money was given to Puerto Rican poor communities to provide clothing, food, and toys for children, and to fund education and housing. On January 6, 1985, sixteen months after the robbery, in an effort to promote their revolutionary cause, three Macheteros commandos gave presents to the children in the heavily-populated Puerto Rican West Hartford neighborhood where Victor Gerena had lived.

Later claiming parallels to the Boston Tea Party, the Macheteros called the Wells Fargo robbery “an act of retaliative expropriation against a federal government that had benefited from the Puerto Rican resources since displacing local farmers during the implantation of the sugar cane industry.”

The Macheteros’ sentiments are not shared by most Puerto Ricans.

The Macheteros Claim They Are

 The Puerto Rican Robin Hoods

When the statehood or independence issues are put on the Boricua ballot, they generally receive only about 5% support; the San Juan Daily Star says the highest amount either measure has gained is 11.8%.

The vast majority of Puerto Ricans fear American separation would plummet their home into a vast dreary wasteland . . . such as Cuba.

Most Puerto Ricans Are Happy

As A Commonwealth

Many American fugitives who have fled to Cuba have reported being imprisoned or forced to live on the street after having their money, home, and possessions confiscated by the government.  Others have lived a life of forced labor on the farms for little or no compensation. A fortunate few were provided little more than the basic necessities of food, running water, and intermittent electricity.

Victor Gerena, similarly, is unlikely to have basked in the good life. He appears to have personally pocketed very little, if any, of the money he had stolen; most, if not all, appears to have gone to the Macheteros or to the Cuban government.

Gerena’s desire for a life of luxury and his ignorance of Cuban history and politics may have made him the perfect pawn for the Macheteros and, by extension, Castro’s Cuba. The wide-eyed security guard turned armed robber probably rues the day he signed on with the Macheteros and set foot on Cuban soil.

The Spoils Did Not Go To Victor

While the Cuban government has let some of its sheltered American fugitives speak to journalists and has even allowed a few to write books, nothing has been learned of Victor Gerena after over forty years. Some believe this suggests Castro may have had him executed shortly upon his arriving on the island or perhaps several years after because he could link the dictator to the Wells Fargo robbery, which the evidence shows he helped plan and finance. This theory may be bolstered by no news of Gerena surfacing even following Castro’s 2016 death.

The FBI, however, says nothing on any of the Macheteros wiretaps or any subsequent evidence suggests Gerena is dead. Some agents instead believe that once he realized his precarious predicament, he, like many other disgruntled islanders, hopped a boat ride to Florida. If he has returned to America to live under a new identity, he has completely stayed off the radar, as he has never contacted any family member or friends.

One of Gerena’s relatives, however, went to great lengths to try to make contact with him.

Was Gerena A Pawn?

In 2001, eighteen years after the Wells Fargo robbery, Gerena’s cousin, Vietnam veteran Francisco Jimenez Gerena, and Hartford Courant journalist Edmund Mahoney traveled to Cuba in an attempt to locate the long-sought fugitive or at least learn what kind of life he was living. Most of their inquiries were met with silence; the few people who said information would soon be forthcoming ultimately clammed up as well.

Francisco Jimenez Gerena

The United States and Cuba have had an extradition treaty since 1904, two years after American military occupation of the island ended following the Spanish-American War. A supplementing 1926 treaty expanded the list of extraditable crimes of fugitives who have fled from one country to the other. Since Castro’s coming to power in 1959, however, the strained relations between the countries with conflicting political ideologies has more often than not resulted in both nations’ noncompliance in returning fugitives.

Although Cuba and the United States restored diplomatic relations in 2015 after fifty-four years, relations remain tepid in large part due to disagreements of fugitive extradition. In recent years, Cuba has returned more absconders requested by the American government, but it still grants asylum to those who are deemed political fugitives, including the West Hartford, Connecticut armored car guard turned perhaps reluctant revolutionary.

The Countries Continue To Clash

Victor Manuel Gerena is wanted for Bank Robbery, Theft From Interstate Shipment, and the Aggravated Robbery of Federal Insured Bank Funds. When last seen in 1983 he stood five-feet-six-inches tall and weighed between one-hundred-sixty to one-hundred-seventy pounds. He was stocky, had a dark complexion, brown hair, and a mole and one-inch scar on his right shoulder blade. His most notable physical feature were his green eyes. In addition to working as a security guard, he had been a machinist, delivery driver, special education teacher’s aide, and peer counselor.

The now sixty-seven-year-old Gerena is probably bald or near balding. Most in the FBI believe he is still in Cuba, living as one of the perhaps upwards of seventy-to-one-hundred American fugitives being sheltered by the island country’s government.

           

Computer-Aged Images Of Victor Gerena

Victor Gerena was placed on the FBI’s Ten Most Wanted List on May 14, 1984, eight months after fleeing with over $7 million.

Since its 1950 inception, four-hundred-ninety-eight of the five-hundred-thirty-seven fugitives, or 93%, of those deemed “the baddest of the bad” have been captured or their remains have been identified. Gerena is one of the failures, having been removed from the list on December 15, 2016, even though he had not been apprehended or confirmed deceased. His tenure as a “top tenner” totaled a record thirty-two years, seven months, and one day.

Although he is no longer on the Ten Most Wanted List, Victor Gerena is still very much wanted. The FBI’s offering up to a $1 million reward for his capture remains active, but as long as the Cuban government continues to grant political asylum, they are unlikely to get their hands on him, and Gerena’s fate, dead or alive, is likely to remain in limbo.

The Longest Top-Ten Tenure

SOURCES:

• America’s Most Wanted
• Connecticut History
• Connecticut Post
• Boston Globe
• FBI
• The FBI Files
• FBI’s Ten Most Wanted by Dary Matera
• Hartford Courant
• Los Macheteros: The Wells Fargo Robbery and the Violent Struggle for Puerto Rican Independence, by Ronald Fernandez
• Unsolved Mysteries