We may earn commission from links on this page, but we only recommend products we back. Why Trust Us?

The U.S. sold Iran dozens of its most capable jet—then spent decades chasing the spies and arms dealers smuggling the parts needed to keep it flying.

The F-14 ripped across the sky toward the oil fields of Khark. Ahead, the battle raged, as Saddam’s bombers targeted tankers filled with petroleum leaving the island’s port. Behind the stick was Col. Jalil Zandi, one of the most fearsome pilots ever to fly the F-14 plane. As Zandi approached the battle, no fewer than eight French-made Mirage fighters came to meet him. He pressed on, undeterred.

The F-14, known as the Tomcat, was a marvel of American aircraft engineering. Produced by Grumman Aerospace, the plane had proved, across hundreds of combat engagements, to be an exceptionally lethal aircraft. With its sophisticated radar system and Phoenix guided missiles, the F-14 could bring down a target from 100 miles away. In closer engagements, its superb maneuvering gave it the edge.

Zandi joined the fray. Throughout the 1980s, F-14 pilots had menaced Saddam’s air force, shooting down more than 100 of its jets. It was common for F-14 pilots to engage three or four Iraqi pilots at once, and the technologically outmatched Iraqis often fled. Still, eight Mirage fighters was pushing it. On that morning in 1988 over Khark, the Mirages stayed to fight. Zandi scored two hits with his close-range Sidewinder missiles before his plane was hit by returning fire. His F-14 crippled, Zandi was forced to disengage, and later eject. But he and his radio officer survived.

Two years earlier, Hollywood and Tom Cruise had elevated the F-14 and the Top Gun program to widespread fame. Zandi was the real-life Maverick. Those two hits on the Iraqi Mirages brought the total number of planes he shot down—called kills—to eight, plus another three probables, making Zandi the top air ace ever to fly the Tomcat. He was an exceptionally brave pilot and a consummate patriot, but there’s a reason you’ve never heard of him: Jalil Zandi wasn’t an American. He fought for the enemy. He fought for Iran.

The story of the Shah’s pilots remains largely hidden. While Grumman was probably delighted by the performance of its signature fighter jet, the U.S. Navy was not going to waste any breath touting the accomplishments of the enemy. Nor was the Ayatollah especially eager to promote the members of his Westernized Air Corps, who’d been trained by American military instructors. But even as this secret war wound down, another, quieter front had already opened: the battle to keep the Iranian F-14 in the air. And that second, hidden battle—a shadow war fought among smugglers, arms dealers, spies, and customs agents—continued for years.

The story of the F-14 begins in the 1960s. The U.S. Navy was looking for a plane that was fast enough to intercept the enemy, nimble enough to win in a dogfight, and light enough to land on an aircraft carrier. Grumman’s “swing wing” F-14 design, which entered service in 1972, was the answer. At subsonic speeds, the jet maintained a classic straight-wing profile, providing impressive maneuverability. As the plane accelerated, the wings could be rotated over 40 degrees aft. With its wings swept back to reduce pressure and drag, the F-14 could reach speeds above Mach 2.

The F-14’s expansive bubble canopy provided excellent visibility, and its cockpit seated two. Behind the pilot sat the radar intercept officer, who monitored a terminal that could track up to 24 targets at once, and who provided the pilot with regular updates on the evolving state of the airspace. (That’s the info Maverick wanted when he yelled, “Talk to me, Goose,” in Top Gun.) Once targets were located, the F-14 was comfortable engaging from a range of distances. It could fire up to six long-range, 1,000-pound Phoenix missiles at once. For closer engagements, the plane used midrange Sparrows and short-range Sidewinders, the latter of which used heat-seeking technology to home in on enemy engines. When all else failed, the pilot could rely on the built-in M61 Vulcan rotary cannon, a Gatling-style machine gun that fired 100 rounds per second.

Despite these lethal capabilities, the development of the F-14 was plagued by cost overruns, and at one point Congress considered canceling it. It was rescued by Mohammad Reza Pahlavi—the Shah of Iran—who at the time was an important American ally. In the mid-1970s the Shah, intent on modernizing his country’s air force, placed a $2 billion order for 80 F-14s, along with hundreds of Phoenix missiles. The deal, titled Persian King, was the largest single foreign military sale in U.S. history.

The U.S. also agreed to train Iranian fighter pilots. Beginning in 1974, Iranian military aviators traveled to the Miramar naval base in San Diego to train with Navy instructors. The F-14 Tomcat repeatedly proved its superiority, besting the rival F-15 Eagle and F-4 Phantom units in simulated dogfights. “At low level, and at low or supersonic speeds, with pilots of equal skill, the F-14A always wins against the F-15A,” one Iranian pilot told the military historian Tom Cooper.

The pilots returned to Iran as the vanguard of their country’s air force, but in 1979 the Shah was overthrown. Ruhollah Khomeini, known as the Ayatollah, then took control. Nothing in the 20th century could have prepared the world for the resulting theocratic state. The Islamic Republic of Iran terrorized its population with strict religious edicts, severely curtailed the rights of women, and seized the U.S. Embassy in Tehran, holding 52 embassy staffers hostage for more than a year. In speeches, Khomeini described the U.S. as “the Great Satan.” The F-14s were now in the hands of the enemy.

Initially, the Ayatollah ordered the F-14s grounded and jailed many of the pilots. But then a second strange and terrible event occurred: In September 1980, Saddam Hussein, the dictator of neighboring Iraq, invaded Iran, sending six divisions of troops across the border. Saddam also staged an air invasion, and Soviet-made aircraft began pummeling positions across the country. The Iranian clerics realized that the Shah’s pilots were too valuable to languish in jail.

A frantic effort began to put the F-14s back in the sky. While Grumman had given the Iranian ground crews hundreds of hours of training on F-14 maintenance, the manufacturer had deliberately withheld some information. “The Americans wouldn’t teach our technical staff anything sensitive about the Tomcat’s avionics, and they wouldn’t let us do anything alone,” one pilot recalls. Following the revolution, many ground crewmen had defected, and American technicians sabotaged some of the Phoenix missiles on their way out. But within a few days of the invasion, the Iranian Tomcats were in the air again.

The first-ever combat kill in an F-14 was scored on September 7, 1980, when a Tomcat pilot downed an Iraqi Mil Mi-25 helicopter with 400 rounds from its Vulcan gun. The kills mounted throughout late 1980, as the Iraqis’ Soviet-made MiG-21 and MiG-23 aircraft proved helpless against the Tomcat’s high-tech weapons platform. The war continued to 1988, ending in a stalemate. In 2015, military analyst John Stillion called the conflict “the largest air war fought anywhere in the world in the past 50 years.”

Over the course of 34 years of service, from 1972 to 2006, American F-14 pilots shot down five enemy aircraft. During that same time, several Iranian pilots claimed that many kills individually. Working from interviews, news reports, and public records, authors Tom Cooper and Farzad Bishop estimated that during the eight years of the Iran-Iraq war, the Iranian F-14 pilots scored 159 total kills—and that was coming from a depleted regime, under heavy sanctions, flying no more than a few dozen planes provided by the Great Satan himself.

Isolated from Western parts and technology, and desperately needing to keep its fleet of F-14s flying, Iran resorted to a network of spies, smugglers, and black-market profiteers. The Iranian quest for American components brought the enemy inside U.S. borders and sparked a decades-long cat-and-mouse game with the Federal agents assigned to shut them down. That clandestine contest continues to this day.

The thoroughbred F-14 was a finicky aircraft; Cooper estimated that every hour an F-14 spent airborne required at least 40 hours of ground-crew maintenance. Everything on the plane seemed to require continuous replacement: actuators for the wings, electronics for the radar, grease for the gun, and spares for the tires. Worst of all were the F-14’s twin Pratt & Whitney TF30 turbofan engines, which were a frequent source of accidents. The engines had been designed for the F111 bomber and weren’t appropriate for the aerial acrobatics of a fighter jet. Assuming a high angle of attack, or making an abrupt adjustment to the throttle, might cause one engine compressor to stall; nine feet away, the other engine would continue thrusting, throwing the plane into an unrecoverable spin. More than 40 U.S. planes were lost due to engine trouble. “The TF30 is just a terrible engine,” former United States Secretary of the Navy John Lehman once told Congress. “I guess the good news is that all the Iranian F-14s have the TF30, too.”

Lack of spares led to many grounded planes. “​​‘During the war, we tried to maintain 60 F-14s in operational condition,” one pilot told Cooper and Bishop. “At first, we more or less managed that, but on average we usually kept between 40 and 45 Tomcats combat ready.” As the war of attrition dragged on, the need grew acute. In 1982, Iran declared a “self-sufficiency jihad,” recruiting engineers and technicians to build simpler parts like brake discs and tires. But the F-14 also required complex computer and avionics components that the self-sufficiency jihadists couldn’t easily replicate. For those parts, the only place to turn was the United States.

Fortunately for Iran, the market for military aircraft parts was surprisingly unregulated. This was true even for F-14 parts, despite the fact that the plane was only ever operated by the U.S. Navy and the Iranian Air Force. With just two potential customers—sworn enemies, no less—a brisk trade developed. And although the U.S. retired the plane in 2006, somehow, nearly 50 years on, the Iranian Air Force has kept the F-14 aloft.

Some of the earliest suppliers to the Iranian Air Force were Israelis. This was certainly odd, as the Iranian regime had cut off all ties with Israel in 1980 and publicly referred to Israel as the “Zionist entity.” Still, in the early 1980s, independent Israeli arms brokers were able to flip F-14 parts they’d secured from American dealers at high prices to Iranian customers. But Iran was also sponsoring Hezbollah, a fundamentalist militia based in Lebanon, and when Hezbollah began firing rockets inside Israel’s borders, the Israeli channel closed.

Iran was also able to secure spare parts from an even stranger source: the Reagan Administration. Readers of a certain age may remember the Iran-Contra affair, one of the more complex political scandals in American history. In 1981, Ronald Reagan had begun secretly negotiating with the Iranian regime, offering to trade arms for several American hostages being held by Hezbollah in Lebanon. In 1985, Col. Oliver North, a decorated Marine Corps veteran working for the Reagan administration, began diverting some of the money from the Iranian arms sales to fund a secret (and illegal) effort to overthrow the government of Nicaragua. The revelation of North’s activities led to his dismissal—and months of congressional hearings. In 1987, Reagan appeared on national television and admitted that he’d repeatedly authorized sales of arms to Iran in exchange for cash and the release of hostages. Some of those arms sales included F-14 components.

After the scandal, the U.S. did not directly supply Iran with parts. But neither did it do a very good job of securing the large number of spares it manufactured for the Navy. In fact, for a long time, responsibility for enforcing the U.S. aircraft-parts embargo fell mostly to two individuals, operating on their own initiative out of a federal office in San Diego. Their names are David Pinchetti and Wendy Duarte, and together they were the Mulder and Scully of the Iran embargo.

Pinchetti had begun his law enforcement career as a watchdog with the Defense Criminal Investigative Service, rooting out corrupt defense contractors who were defrauding U.S. taxpayers. After a number of successful bribery and bid-rigging convictions, he turned to busting smugglers in the late 1990s. Duarte, a U.S. Customs agent, joined him on a two-person task force. From the beginning, Pinchetti was astonished by the stupidity of the U.S. military surplus disposal approach. Most parts were disposed of through public auctions, run by an obscure federal agency called the Defense Reutilization and Marketing Service. “The Navy had all these very expensive components. They’re not really flying the aircraft anymore, but they still put them into the system,” he said. “And the only country that was still flying one of these things was Iran!”

Duarte and Pinchetti’s first major case was that of Saeed Homayouni, an Iranian-born petroleum engineer based in Bakersfield, California. Homayouni, a Canadian citizen, worked a quiet job at the local oil company, lived in a modest apartment, and had no obvious romantic or social life. In his spare time, he’d fax requests to aircraft-parts brokers, seeking price quotes for military components. (While such parts were subject to export controls, at the time there were few restrictions on domestic trade.) When the parts arrived, Homayouni would sign for them using the alias Sid Hamilton.

Pinchetti and Duarte’s investigation into Homayouni began in 1999, when a concerned vendor sent the two a tip. After a little digging, Pinchetti and Duarte came to suspect that Homayouni’s brother Soroosh, based in London, was shuttling money between Bakersfield and Tehran, using a front company called Multicore Ltd. Soroosh was clumsy, and he had been investigated by U.S. Customs before. In Bakersfield, Saeed Homayouni had been more careful, and may have been operating the scheme for years.

For months, Duarte and Pinchetti watched as FedEx and UPS delivered a stream of F-14 and other aircraft components to Homayouni’s apartment. These included F-14 air-duct intake seals, a harness for an F-14 fuel indicator, components for an ejector seat, and even a portion of an F-14 cockpit canopy. The deliveries often came with an official federal warning that the part was under export control. Still, Pinchetti was surprised that such sensitive parts could be ordered by the public at all. “He was buying electron tubes, and magnetron tubes, and some of those things were, like, $20,000!” Pinchetti said.

After securing a part, Homayouni would scrub off any labeling that would identify its military origins, then place it in a storage locker. Using a rented mailbox, he’d then ship the part to Singapore, while filing a false customs declaration, claiming the parts were either low-value civilian aviation components or simple consumer electronics. From there, the parts made their way to Iran, with the assistance of Soroosh’s Singapore-based girlfriend.

Pinchetti and Duarte arrested Homayouni in December 2000, after watching him for almost two years. The evidence against him included discarded faxes that Duarte had retrieved from his trash. At the time of his arrest, Homayouni had two storage lockers that were full of aircraft components; a subpoena of his bank records showed that over the course of a single 13-month period, he’d ordered more than $2 million worth of military aircraft parts. Another bank account had $1.4 million stashed inside. “That was pure profit,” Pinchetti said.

Homayouni served two years in prison and was subsequently deported, but Pinchetti was never able to determine whether he was a spy, or merely a profiteer. The high margins on F-14 parts attracted opportunists, even flamboyant ones. One such player was Arif Durrani, a garrulous Pakistani arms dealer—and consummate bullshit artist—who was twice convicted of violating the U.S. arms embargo on Iran.

Durrani was first convicted of selling missile parts to Iran in 1986. (He claimed the sale was authorized by Oliver North.) Following his imprisonment and deportation, Durrani moved to Mexico, immediately south of the U.S. border, and opened a restaurant. Frequently wearing a bomber jacket and aviator sunglasses, Durrani began recruiting Americans to act as fronts, who would purchase aircraft parts on his behalf—including a retired Department of Defense intelligence officer.

Unlike the patient Homayouni, Durrani was essentially improvising arms deals on the fly. “There’s a tremendous network of brokers who never have the part at all,” William Cole, the former U.S. prosecutor who brought the second case against Durrani, told me. “They just get the order, and they go find it somewhere else.” Durrani was skilled at this. “He needed some nozzles for F-14 engines,” Cole said. “So they find them in a shop in New Jersey, and they need refurbishing. They find some other shop to do that, and they sell it for a huge multiple.” Cole estimated Durrani made about 20 times profit on the deal, without ever leaving his restaurant in Mexico.

Durrani’s luck ran out in 2005, when he was caught in an unrelated immigration dragnet run by Mexican authorities and ordered back to Pakistan. U.S. authorities convinced the Mexican government to route Durrani’s flight home through LAX. He was arrested at the airport by U.S. Customs agents and charged with conspiracy, one of the few smuggling cases that made it to trial. “The name of his firm was Aerospace Logistics,” Cole said. “On the stand, he tried to tell the jury it was a furniture business.” Durrani was found guilty and sentenced to 12 years.

By the mid-2000s, enforcing the Iran embargo had grown to a dedicated law enforcement beat. Pinchetti and Duarte’s small office expanded to a team of around a dozen agents, including intelligence analysts and liaisons with the CIA. But even with such resources, Pinchetti still felt that the government wasn’t taking the smuggling seriously. At the resolution of the Homayouni case, the Feds had seized his lockers full of aircraft parts. Then, in an unforgettable flourish of bureaucratic incompetence, another branch of the government had auctioned the seized parts back to the public. “The government sold it off again!” Pinchetti told me, still in disbelief. “I’d be on search warrants where we’d find the stuff someplace else. Some of the old evidence tags were still on it!”

To what degree the smuggling networks were coordinated by Iranian intelligence was something Pinchetti was never able to completely determine. Sometimes he felt like he was chasing an organized spy network. Other times he felt like he was prosecuting junkyard hustlers. He was given a clue, though, in 2006, on the last big case of his career. Airplane parts were one thing, but this case involved the resale of high-grade accelerometers from the manufacturer Hamilton Sundstrand. “They’re like a small computer chip with these little wires, and they cost about $110,000 apiece,” Pinchetti said of the accelerometers. “These things are spec’d out to incredible g-forces. Basically, they can go into space. And the Iranians wanted them really, really bad—probably to make ICBMs.”

Using two informants from a previous case, Pinchetti ran a sting on the buyer, who turned out to be Jamshid Ghassemi, a colonel in the Iranian military whom Pinchetti believed was targeting American military surplus sales networks. Ghassemi, operating out of Bangkok, was too smart to set foot in the United States, but after Pinchetti’s informants convinced him to wire $70,000 to an American bank account as a down payment, he was arrested by Thai authorities and thrown in prison.

Most of Pinchetti’s targets pleaded guilty quickly and cooperated in exchange for leniency. But Ghassemi didn’t crack. He spent almost two years in a Thai jail as Iran and the U.S. fought a heated legal battle over his extradition. In 2008, with his own father dying, Pinchetti delayed his retirement so he could travel to Thailand and lay eyes on his adversary. In court, Pinchetti saw a tall man in his 50s—roughly Pinchetti’s own age—who had not a word to say. Was this the architect? “He was pretty hard-core,” Pinchetti said. “A true believer in the Iranian revolution.” In September 2008, the American extradition request was denied, and Ghassemi returned to Tehran. The independent monitor Iran Watch later reported his promotion to general.

In June 2007, on a military base on the outskirts of Tucson, Arizona, a giant metal claw grabbed the fuselage of an F-14 and began tearing it into scrap. A year earlier, the Navy had retired all remaining Tomcats, after their commendable 34-year run. But rather than place the surplus aircraft in a museum or sell them to private collectors, the military had ordered them destroyed. The revelation that the public could buy fighter jet parts—and ICBM components!—from military surplus dealers was a bit much, even for Congress. At last, the government was taking the parts trade seriously, if perhaps a little heavy-handedly.

Over the next two weeks, dozens more F-14s would be shredded. “There were things getting to the bad guys, so to speak,” Tim Shocklee, who managed the demolition, told reporters at the time. “And one of the ways to make sure that no one will ever use an F-14 again is to cut them into little 2-by-2-foot bits.” Similar scenes of destruction played out across the country that year, as authorities seized F-14s from museums and private collectors and tore out any sensitive components. In a gesture more symbolic than practical, every single part of the plane was destroyed, including the plane’s heavily reinforced landing gear, which braced the F-14 when it slammed onto the deck of an aircraft carrier. Strong enough to withstand the power of the claw, the gear was cut in half with a demolition torch.

Since the 2007 lockdown, Iran has pivoted from fighter jets to killer drones. The embargo remains in place; so, apparently, do the smuggling networks. Teardowns of Iranian suicide drones used by Russia in Ukraine have found embargoed American components, including semiconductors and weapons-grade inertial measurement units. “In three UAV models, we saw more than 500 different components,” said Damien Spleeters, of Conflict Armament Research, who conducted the teardowns. “About 82 percent of these components were made in the U.S.”

But even as Iran projects power abroad, it struggles at home. Fed up with decades of repression, economic deprivation, and abuse, Iranian protesters are staging increasingly bold actions against the regime. Over the past 18 months, thousands have taken to the street to demand reforms; the mullahs have responded with lethal force, torture, and public executions. In November, protesters set fire to the Ayatollah’s boyhood home. Several days later, at the World Cup, the players of the Iranian national soccer team declined to sing their country’s national anthem.

Facing such civil unrest at home, the Iranian Air Force has kept the F-14 flying. The military value of the aircraft in the modern era is questionable, but, as Tom Cruise can attest, its propaganda value is unparalleled. In 2015, an Iranian news agency released photographs of the overhauled F-14s, revealing that the self-sufficiency jihad was by this point quite advanced. The Iranian engineers had managed to recreate the long-range Phoenix missile, rebranding it “the Fakour.” The sensitive avionics and computer components seemed to have been mostly re-engineered. Over Syria that year, two F-14s had accompanied a Russian-made Tu-95 on a bombing run. Video showed the planes, the last known survivors of their species, racing against a clear blue sky.

Ukraine Is Getting Bridge-Laying Patton Tanks

Why the U.S. Is Evaluating Two Ukrainian Pilots

Russian Cargo Plane Explodes During Pressure Test

Watch Opposition Group Land Drone on Russian Jet

Pentagon's Mysterious Aircraft Won't Need a Runway

Report: Pilot Error Ruined a $112 Million F-35 Jet

Air Force Grounds Jets: Their Tails May Fall Off

The Messy Battle to Build the F-35's Next Engine

The Super Hornet Is Going to Die

F-14 Fighters, Treasure Hunts, and More

The Rumored U-2/Spy Balloon Selfie is Real

Why the Air Force Wants a Stealthy Tanker by 2040

A Part of Hearst Digital Media

Gear-obsessed editors choose every product we review. We may earn commission if you buy from a link.

©Hearst Magazine Media, Inc. All Rights Reserved.