ON A MILD SPRING DAY IN LATE MAY 1987, military analyst John Pike was at the U.S. embassy in Moscow on business when he looked out the window and saw a small airplane circling over Red Square. Gee, that’s peculiar, thought Pike. There’s no private aviation in the Soviet Union. Hell, there’s no private anything.

The aircraft belonged to West German teenager Mathias Rust—or, more accurately, to Rust’s flying club. In a daring attempt to ease cold war tensions, the 19-year-old amateur pilot had flown a single-engine Cessna nearly 550 miles from Helsinki to the center of Moscow—probably the most heavily defended city on the planet—and parked it at the base of St. Basil’s Cathedral, within spitting distance of Lenin’s tomb. Newspapers dubbed the pilot “the new Red Baron” and the “Don Quixote of the skies.” The stunt became one of the most talked-about aviation feats in history. But it was politics, not fame, that motivated Rust.

There is nothing in Rust’s neat two-bedroom apartment outside Berlin—no mementos, no photographs, no framed newspaper headlines—nothing at all to indicate that for a few short weeks 18 years ago he was the most famous pilot in the world. But the memory of the flight has stayed fresh. “It seems like it happened yesterday,” says Rust, now 36. “It’s alive in me.”

As a child in Hamburg, Rust had been preoccupied by two things: flying and nuclear Armageddon. Belligerence and distrust marked East-West relations of the time. U.S. President Ronald Reagan seemed to be on a personal crusade against the Soviet Union. Many Germans were on edge. “There was a real sense of fear,” Rust says, “because if there was a conflict, we all knew we would be the first to be hit.”

To many Europeans, Mikhail Gorbachev’s ascendancy to the Soviet leadership in 1985 offered a glimmer of hope. Glasnost, his policy of transparency in government, and perestroika, economic reforms at home, were radical departures from the policies of his predecessors. So when the U.S.-Soviet summit in Reykjavik, Iceland, in October 1986 ended without an arms reduction deal, Rust felt despair. He was particularly angered by Reagan’s reflexive mistrust of the Soviet Union, which Rust felt had blinded the president to the historic opportunity Gorbachev presented.

Rust decided he must do something—something big. He settled on the idea of building an “imaginary bridge” by flying to Moscow. If he could reach the Soviet capital, if he could “pass through the Iron Curtain without being intercepted, it would show that Gorbachev was serious about new relations with the West,” says Rust. “How would Reagan continue to say it was the ‘Empire of Evil’ if me, in a small aircraft, can go straight there and be unharmed?” Rust also prepared a 20-page manifesto he planned to deliver to Gorbachev on how to advance world peace.

Rust had taken his first flying lessons only a couple of years before his decision to fly to Moscow. A data processor at a mail-order trinket company, he spent all of his money (and some of his parents’) flying. But by the spring of 1987, he had barely 50 hours of licensed flight time, and had completed just a handful of cross-country trips.

“I thought my chances of actually getting to Moscow were about 50-50,” Rust says, noting that in 1983, the Soviets blew Korean Airlines flight 007 out of the sky after it strayed into Soviet airspace near the Kamchatka Peninsula; all 269 persons aboard were killed. “But I was convinced I was doing the right thing—I just had to dare to do it.”

To prepare himself for his mission, he planned a practice flight to Reykjavik, the site of the doomed arms talks. It would be “a long time flying over open water with very little navigation aids,” says Rust. “I figured if I succeeded, I would be able to cope with the pressure of flying to Moscow.”

Rust meticulously planned his route and signed out a 1980 Cessna Skyhawk 172 from his flying club for three weeks. The four-seat airplane was equipped with auxiliary fuel tanks that boosted the aircraft’s range by 175 nautical miles to 750 nautical miles—range he would need in order to safely reach Reykjavik, and later Moscow. The club didn’t ask him where he was going, and Rust didn’t say. He packed a small suitcase, a satchel with maps and flight planning supplies, a sleeping bag, 15 quarts of engine oil, and a life vest. As a final precaution, Rust packed a motorcycle crash helmet. The helmet was for his final leg to Moscow, “because I didn’t know what [the Soviets] would do, and if I was forced down it would give me extra protection [in case of a crash].”

On May 13, 1987, Rust took off from Uetersen Airfield, outside Hamburg, and flew for five hours across the Baltic and North seas before reaching the Shetland Islands. The next day he flew to Vagar, on Denmark’s Faröe Islands, in the middle of the north Atlantic. On May 15 he flew to Reykjavik.

Rust spent a week in the Icelandic capital. He visited Hofdi House, the white villa that was the site of the Reagan-Gorbachev summit. “It was locked,” Rust says, “but I felt I got in touch with the spirit of the place. I was so emotionally involved then and was so disappointed with the failure of the summit and my failure to get there the previous autumn. So it gave me motivation to continue.”

On May 22, Rust set out for Finland by way of Hofn, Iceland; the Shetlands; and Bergen, Norway. He landed at Malmi airport in Helsinki on May 25. Since leaving Hamburg, he had covered nearly 2,600 miles and had doubled his total flight time to more than 100 hours. He had proven to himself he had the flying skills he needed, but he still had doubts about his nerve. His resolve constantly wavered: Yes, it was something he had to do/No, it was crazy.

The night of May 27 was a restless one for Rust. In the morning he drove to the airport, fueled the Cessna, checked the weather, and filed a flight plan for Stockholm (“My alternate if I chickened out,” he says), a two-hour trip to the southwest.

At about 12:21 p.m., Rust took off. Controllers at Malmi had him turn west toward Stockholm, asking him to keep the airplane low to avoid traffic. Although the Cessna was equipped with a transponder, a device that transmits a response to radar interrogation and thus helps to identify an aircraft, Helsinki controllers didn’t assign him a setting, so he turned the device off—the controllers would track Rust’s airplane by the reflection of radar signals off its metal skin. Rust held course for about 20 minutes, at which point controllers radioed to say he was leaving their control area. Rust thanked them and said goodbye.

He continued toward Stockholm for several minutes; then, as he closed in on his first waypoint, near the Finnish town of Nummela, he chose. “All of a sudden, I just turned the airplane to the left [toward Moscow],” he says. “It wasn’t really even a decision…. I wasn’t nervous. I wasn’t excited. It was almost like the airplane was on autopilot. I just turned and headed straight across [the Gulf of Finland] to the border.”

At the Tampere air traffic control facility in Finland, controllers noticed Rust’s near-180-degree change of course. As the radar blip headed south and then east across the water, passing through restricted Finnish military airspace, controllers tried to contact him and failed. At about 1 p.m., Rust’s airplane disappeared from radar screens. Fifteen minutes later, a helicopter pilot radioed that he spotted an oil slick and some debris on the water near where Rust’s airplane was last detected. A search-and-rescue operation was activated—only to be called off when news of Rust’s landing reached Finland. (Years later Finnish aviation authorities investigated a series of incidents in which airliners mysteriously disappeared from Tampere radar screens while in the same area.)

Meanwhile, at a radar station in Skrunda, now in the independent state of Latvia, Soviet military personnel were also tracking Rust. All foreign aircraft flying into the Soviet Union were required to get a permit and to fly along designated corridors, and Rust’s was not an approved flight. As the unidentified aircraft neared the coastline at around 2:10 p.m. Moscow time (an hour ahead of Helsinki), three missile units were put on alert.

From Helsinki, Rust’s flight plan was simple: Turn to a heading of 117 degrees and hold course. As he crossed his first waypoint, the Sillamyae radio beacon near Kohtla-Jarve, on the coast of the now-independent state of Estonia, he climbed to 2,500 feet above sea level, a standard altitude for cross-country flight, which would keep him about 1,000 feet above the ground for the entire route. He trimmed the airplane out and flew straight and level. He also put on his crash helmet. “The whole time I was just sitting in the aircraft, focusing on the dials,” says Rust. “It felt like I wasn’t really doing it.”

Soviet controllers continued to monitor the unidentified airplane’s progress. Now that it was well inland, army units in the area were put on high alert and two fighter-interceptors at nearby Tapa air base were scrambled to investigate. Peering through a hole in the low clouds, one of the pilots reported seeing an airplane that looked similar to a Yak-12, a single-engine, high-wing Soviet sports airplane that from a distance looks very similar to a Cessna. The fighter pilot, or his commander on the ground, perhaps thinking the airplane must have had permission to be there, or didn’t pose any threat, decided the airplane did not require a closer inspection.

Not long after being seen by the Soviet fighter pilot, Rust descended in order to avoid some low clouds and icing. For a brief period, his blip disappeared from Soviet radar screens. Once the weather cleared, Rust climbed back to 2,500 feet, and an image of the unidentified airplane appeared on the radar screen in a new sector, one whose commander ordered two more fighter-interceptors to investigate.

Now nearly two hours into his flight, Rust says the sun was shining when he saw “a black shadow shooting in the sky and then disappear.” A few moments later, from out of a layer of clouds in front of him, an aircraft appeared. “It was coming at me very fast, and dead-on,” Rust recalls. “And it went whoosh!—right over me.

“I remember how my heart felt, beating very fast,” he continues. “This was exactly the moment when you start to ask yourself: Is this when they shoot you down?”

From below and to the left, a Soviet MiG-23 fighter-interceptor pulled up beside him. With nearly three times the wingspan and more than 10 times the weight of Rust’s Cessna, the MiG seemed huge. Designed to fly at more than twice the speed of sound, the swing-wing fighter had to be put into full landing configuration—gear and flaps extended, wings swung outward—in order to slow it enough to fly alongside the Cessna. Its nose rode high as it hovered at the edge of a stall.

“I realized because they hadn’t shot me down yet that they wanted to check on what I was doing there,” Rust says. He kept watching the Soviet airplane, “but there was no sign, no signal from the pilot for me to follow him. Nothing.” Soviet investigators later told Rust that the MiG pilot attempted to reach Rust over the radio but there was no response. Only later did Rust realize that the Soviet fighter could only communicate over high-frequency military channels.

After the two pilots had eyed each other for a minute, the Soviet pilot retracted the jet’s gear and flaps. The MiG accelerated and peeled away, only to return and draw two long arcs around the Cessna at a distance of about a half-mile. Finally, it disappeared.

From both the registration number painted on the side of the airplane (D-ECJB) and the West German flag decal on its tail, the MiG-23 crew should have been able to tell that Rust’s aircraft was neither a Yak nor Soviet. Marshall Sergei Akhromeyev, chief of staff of all the Soviet armed forces, admitted in a 1990 interview cited in Don Oberdorfer’s book From the Cold War to the New Era that the fighter pilot’s commander either did not believe the pilot’s report or did not think it was significant, so the information was never passed up the chain of command.

At 3 p.m., with the weather improving, Rust entered a Soviet air force training zone where seven to 12 aircraft—all with performance characteristics and radar signatures similar to Rust’s—were being used in training exercises such as takeoffs and landings.

Rust’s altitude probably helped him appear harmless. Had he attempted to evade radar, as many later speculated he did, the Soviets likely would have taken more aggressive action to stop him, but even in that scenario, the Soviets’ options for dealing with him were fairly limited. Since the KAL 007 tragedy, strict orders were given that no hostile action be taken against civilian aircraft unless orders originated at the very highest levels of the Soviet military, and at that moment, Defense Minister Sergei Sokolov and other top military commanders were in East Berlin with Gorbachev for a meeting of Warsaw Pact states.

As a security procedure, Soviet radar has aircraft under its control regularly reset their transponder codes at prearranged times. If a pilot failed to make the switch, his airplane’s radar signature would look “friendly” one minute and “hostile” the next, after the ground had switched over. On the day of Rust’s flight, 3 p.m. was one of those times. As Rust proceeded, a commander looking over the shoulder of a radar operator—apparently thinking Rust’s radar return was that of a student pilot who had forgotten to make the transponder switch—ordered the officer to change the Cessna’s radar signature to “friendly.” “Otherwise we might shoot some of our own,” he explained.

By 4 p.m., Rust crossed radar sectors near Lake Seliger, a popular summer retreat near the town of Kushinovo, about 230 miles from Moscow. As the radar return for the Cessna popped up on a new set of radar screens, controllers once again took note of the unidentified aircraft. Once again a pair of fighter-interceptors was launched to investigate, but according to a Russian report on Rust’s flight, commanders considered it too dangerous for the airplanes to descend through the low cloud deck, so visual contact was never made. Rust was now a little more than two and a half hours away from his destination.

About 40 miles west of the city of Torzhok, another radar controller saw the signal for Rust’s airplane and assumed it was one of two helicopters that had been performing search-and-rescue operations nearby. On his radar screen, he flagged it as such, and once again Rust’s airplane was marked as a “friendly.”

Rust flew on, leaving the Leningrad military district and entering that of Moscow. In the handoff report, the Leningrad commander related to his Moscow counterpart that his controllers had been tracking a Soviet airplane flying without its transponder turned on. But the report said nothing about tracking an unidentified airplane from the Gulf of Finland, nothing about fighter-interceptors intercepting a West German aircraft, and nothing about an unidentified aircraft on a steady course to Moscow. As such, the report set off no alarms.

For Rust, the flight was going flawlessly. He had no problem identifying the landmarks he had chosen as waypoints, and he was confident that his goal was within reach. “I had a sense of peace,” he says. “Everything was calm and in order.” He passed the outermost belt of Moscow’s vaunted “Ring of Steel,” an elaborate network of anti-aircraft defenses that since the 1950s had been built up as a response to the threat of U.S. bombers. The rings of missile placements circled the city at distances of about 10, 25, and 45 nautical miles, but were not designed to fend off a single, slow-flying Cessna.

At just after 6 p.m., Rust reached the outskirts of Moscow. The city’s airspace was restricted, with all overflights—both military and civilian—prohibited. At about this time, Soviet investigators would later tell Rust, radar controllers realized something was terribly wrong, but it was too late for them to act.

As Rust made his way over the city, he removed his helmet and began to search for Red Square. Unlike many western cities, Moscow has no skyline of glittering office towers that Rust could see and head for. Unsure where to go, Rust headed from building to building. “As I maneuvered around, I sort of narrowed in on the core of the city,” he says. Then he saw it: the distinctive turreted wall surrounding the Kremlin. Turning toward it, Rust began to descend and look for a place to land.

“At first, I thought maybe I should land inside the Kremlin wall, but then I realized that although there was plenty of space, I wasn’t sure what the KGB might do with me,” he remembers. “If I landed inside the wall, only a few people would see me, and they could just take me away and deny the whole thing. But if I landed in the square, plenty of people would see me, and the KGB couldn’t just arrest me and lie about it. So it was for my own security that I dropped that idea.”

As he circled, Rust noticed that between the Kremlin wall and the Hotel Russia, a bridge with a road crossed the Moscow River and led into Red Square. The bridge was about six lanes wide and traffic was light. The only obstacles were wires strung over each end of the bridge and at its middle. Rust figured there was enough space to come in over the first set of wires, drop down, land, and then taxi under the other wires and into the square.

Rust came in steeply, with full flaps, his engine idling. As planned, he came in over the first set of wires, dropped down, and flared for landing. As he rolled out under the middle set of wires, Rust noticed an old Volga automobile in front of him. “I moved to the left to pass him,” Rust says, “and as I did I looked and saw this old man with this look on his face like he could not believe what he was seeing. I just hoped he wouldn’t panic and lose control of the car and hit me.”

Rust passed under the last set of wires and rolled onto the square. Slowing, he looked for a place to park. He wanted to pull the airplane into the middle of the square, in front of Lenin’s tomb. But surrounding St. Basil’s Cathedral was a small fence with a chain strung across it that blocked his way. Rust pulled up in front of the church.

He shut down the engine, then closed his eyes for a moment and sucked in a deep breath. “I remember this great feeling of relief, like I had gotten this big load off my back.” He looked at the Kremlin clock tower. It was 6:43 p.m., almost five and a half hours since he’d left Helsinki.

He got out of the Cessna. Expecting to be stormed by hordes of troops and KGB agents, Rust leaned against the aircraft and waited. The people in Red Square seemed nervous or stunned, not sure what was going on. Some thought Rust’s airplane might be Gorbachev’s private aircraft, or that it was all part of a movie production. But once the crowd realized that Rust and the Cessna were foreign—and that he’d just pulled off one of the most sensational exploits they had ever witnessed—they drew closer.

“A big crowd had formed around me,” Rust says. “People were smiling and coming up to shake my hand or ask for autographs. There was a young Russian guy who spoke English. He asked me where I came from. I told him I came from the West and wanted to talk to Gorbachev to deliver this peace message that would [help Gorbachev] convince everybody in the West that he had a new approach.”

The atmosphere was festive. One woman gave him a piece of bread as a sign of friendship. According to Rust, an army cadet told him that “he admired my initiative, but that I should have applied for a visa and made an appointment with Gorbachev—but he agreed that they most likely would not have let me.”

Rust did not notice that KGB agents were moving through the crowd, interviewing people and confiscating cameras and notebooks. More than an hour after the landing, two truckloads of armed soldiers arrived and roughly shoved the crowd away. They also put up barriers around the airplane.

Three men emerged from a black sedan and introduced themselves. The youngest, an interpreter, politely asked for Rust’s passport and whether he was carrying any weapons. They then asked to inspect the aircraft. After a few more questions, they asked Rust to get into the car. The mood, Rust says, was still very friendly, almost mirthful. The Cessna was hauled to Moscow’s Sheremetyevo International Airport and disassembled for inspection. Rust was taken to Lefortovo prison, a notorious complex the KGB used to hold political prisoners.

Given the level of planning put into the flight, as well as the number of obstacles that had apparently been overcome, the Soviets could not believe that this was the work of one man, much less an idealistic boy. Investigators believed Rust’s journey was part of a much larger plot. Take the date itself, May 28. It was Border Guards Day. Many speculated Rust chose that day thinking the border would be more lightly defended, or perhaps to maximize the embarrassment the flight would cause the military. “I didn’t know about it,” Rust says. “I said, ‘I’m a West German. How should I know about your holidays?’ It was just a lucky circumstance.” His interrogators also accused him of obtaining maps from the CIA or the German military, but when the Soviet consul general in Hamburg was able to obtain the same maps from a mail order company, as Rust had, the interrogators relented.

Rust’s investigators showed him photographs of the bridge he’d landed on. In the photos, many sets of wires stretched across the bridge, each about six feet apart. They asked Rust how he could possibly land with so many wires in his way. Perplexed himself, Rust explained that when he landed he could see only three sets of wires. Upon further investigation, the Soviets learned that the morning of the day Rust landed, a public works crew had removed most of the wires for maintenance; they were replaced the next day. “They said I must have been born with a shirt”—a Russian expression meaning born lucky.

One German periodical published a story saying Rust did the stunt on a bet. Another reported that he did it to impress a girl. Yet another said he did it in order to drop leaflets seeking to free nonagenarian Rudolf Hess, Hitler’s lieutenant, from jail. The Communist newspaper Pravda accused Rust of being a patsy in an international plot in which he was supposed to have been shot down and killed in order to provoke an international incident. However ridiculous the rumors were, the Soviets methodically looked into every allegation.

On June 23, 1987, the Soviets completed their investigation. Shortly afterward, prosecutors charged Rust with illegal entry, violation of flight laws, and “malicious hooliganism.” Rust pleaded guilty to all but the last charge. There was, he argued, nothing malicious in his intentions.

On September 4, after a three-day trial, a panel of three judges found Rust guilty of all charges and sentenced him to four years at Lefortovo. The prison, though starker and more restrictive than a labor camp, ensured Rust’s safety. He spent his time there quietly and was afforded special privileges: He was allowed to work in the garden and receive visits by his parents every two months.

On August 3, 1988, two months after Reagan and Gorbachev agreed to a treaty to eliminate intermediate-range nuclear weapons in Europe, the Supreme Soviet, in what Tass described as a “goodwill gesture,” ordered Rust released from prison.

According to William E. Odom, former director of the National Security Agency and author of The Collapse of the Soviet Military, Rust’s flight damaged the reputation of the vast Soviet military and enabled Gorbachev to remove the staunchest opponents to his reforms. Within days of Rust’s landing, the Soviet defense minister and the Soviet air defense chief were sacked. In a matter of weeks, hundreds of other officers were fired or replaced—from the country’s most revered war heroes to scores of lesser officers. It was the biggest turnover in the Soviet military command since Stalin’s bloody purges of the 1930s.

More important than the replacement of specific individuals, analyst John Pike says, was the change Rust’s flight precipitated in the public’s perception of the military. The myth of Soviet military superiority had been punctured, and with it the almost religious reverence the public had held for its armed forces.

For decades, Soviet citizens had been led to believe “the West was poised to destroy them…that if they let their guard down for an instant that they would be obliterated,” says Pike. It was this thinking that helped perpetuate the cold war. Rust’s flight proved otherwise: The Soviet Union could suffer a breach without being destroyed by external forces. Ultimately, of course, it would be internal forces that would do the job.

The flying club’s Cessna changed hands several times (in 1988, it was listed for sale in Trade-A-Plane) before ending up with a Japanese developer who intended to make it an attraction at an amusement park. That project went bankrupt and the airplane disappeared.

Rust never piloted an airplane again. In fact, he spent many years trying to distance himself from his famous flight. In 2002 he founded a mediation service designed to “fight violence by providing proper redress,” for which he has spent a lot of time in the Middle East, mostly in Palestinian territories, but to help pay the bills Rust also works for a London-based investment firm.

Though frustrated that he never got to meet Gorbachev, he takes satisfaction in having had a small but important impact on relations between the superpowers. Four years after his “mission,” the forces that his flight helped to strengthen dissolved the Soviet Union, and the cold war ended.