For several days in May 2013, the Hollywood sting operation surveilled the grandfather at the condominium he sometimes shared with his ex-wife in the tony San Diego district of Bankers Hill. A $30,000-a-week private security group, armed because they deemed their subject a hostile threat, watched his movements aboard the 45-foot cruiser Poverty Sucks, docked nearby. They tracked him at his boat shop, Coronado Precision Marine. And they followed him to his local P.O. box. When they felt confident that they'd clocked his routine, they sent in Tom Colbert, the veteran newsman who'd hired them. He wore a wire and a hidden camera in his glasses.
They'd opted for an ambush after their target, a decorated Vietnam veteran whose extensive training included psy ops, didn't bite on Colbert's original cover plan: to lure him with the offer of consultant work on a fictitious TV show about a group of mercenaries, in the vein of The A-Team or The Expendables. "I'd thought, 'Why don't we try to do our own Argo?'" he recalls. Colbert had grown convinced that this old U.S. Army soldier with a distinctive criminal record, Robert W. Rackstraw, was in fact D.B. Cooper, who in 1971 skyjacked a Boeing 727 and then — with $200,000 in ransom money — parachuted from the plane into the Pacific Northwest night and enduring American myth.
At the boat shop, Colbert got straight to it, rolling out a chart the size of a table, which drew links between Rackstraw and the ransom. "Why are you in the middle of this, Bob?" Colbert said, before switching gears to a sales pitch, offering a pair of $10,000 cashier's checks made out in Rackstraw's name if he'd sign over his story rights for a planned documentary and accompanying book. Colbert, a figure with a long history in Hollywood's true stories business, explained that he already had enough material for his project to make it viable, but he'd much prefer Rackstraw's participation. There'd be further paydays when the movie and book were released. The catch: "I wanted him to come clean," says Colbert. "Several attorneys told me the most he was going to get was two to three years. I told him he might get time served and probation. He'd wear an ankle bracelet and never have to buy a beer again the rest of his life."
Rackstraw wouldn't commit. So Colbert later emailed with a harder sell, advising that if he didn't get on board, he and everyone who knows him would be hounded forever. But if Rackstraw gave in, Colbert would "work to keep your neighborhood media-free and peaceful. Sign away and I'll make it all happen."
Instead, Rackstraw turned his attorney on Colbert. This exchange would be the only direct contact between the symbiotic pair. But their spiraling feud over Rackstraw's alleged identity, and the possible fame and fortune to be gotten in the telling, would persist for another six years. Only Rackstraw's passing in July — of a heart condition, at 75 — would change their deadlocked calculus.
The ballad of Rackstraw and Colbert is a lesson in the lures and dangers of chasing the truth while also chasing a Hollywood deal.
Decades before today's true-crime boom and the neo-vigilantism of The Jinx and Serial, there was D.B. Cooper. The mystery — who was he and what happened to him? — has been a pop culture obsession ever since. It's been referenced in song lyrics (everyone from Kid Rock to MF Doom) and been the subject of feature films — Treat Williams played Cooper and Robert Duvall an insurance investigator chasing him in 1981's crime thriller The Pursuit of D.B. Cooper; a camping trip in search of the Cooper cash was at the center of 2004's Without a Paddle. Kyle MacLachlan's protagonist in Pacific Northwest drama Twin Peaks is perhaps not coincidentally named Dale Bartholomew Cooper, and during Mad Men the theory that Don Draper had been the skyjacker became so noisy that showrunner Matthew Weiner had to debunk it.
The skyjacking occurred Nov. 24, 1971. Once the plane was in the air, a man wearing dark sunglasses who'd purchased a ticket at Portland's airport under the alias Dan Cooper — later misreported as D.B. Cooper — told a flight attendant he had a bomb. He demanded that the ransom money and four parachutes be delivered to him when the plane landed in Seattle.
The passengers were exchanged for the ransom. After refueling, Cooper signaled a course for Mexico at the minimum possible speed, opened the aft door and plunged into the wilderness. (The plane then landed safely in Reno.)
Cooper skyjacked in an unrecognizable America, when planes were still tantamount to ocean liners with wings and passengers still smoked onboard with abandon. The following year the FAA issued emergency rules requiring the screening of passengers and their carry-on baggage. His escapade, along with a spike in copycat skyjackings the following year — some by military veterans with parachuting experience — were the catalyst for the modern security apparatus that now envelopes air travel.
Nearly half a century on, Cooper remains a mystery. Only Amelia Earhart and Jimmy Hoffa rival his hold on the public imagination. And as with those others, a cottage industry of sleuths has arisen around the case. Call it the Coopersphere.
At its center is 62-year-old Colbert, who claims to have spent $250,000 in his search to unmask the criminal, initially expecting he'd make his money back in a few years on book and movie deals. An affable, exuberant personality — Tom Arnold comes to mind — who now resides in Ventura County, Colbert is a colorful, old-school newsroom specimen. He worked as a field producer and researcher alongside then up-and-comers Paula Zahn, Ann Curry and Lester Holt at KCBS. (Another colleague from the period, Connie Chung, says she is unsurprised by Colbert's Cooper hunt, given his "indefatigable curiosity to uncover the truth.")
After a sour follow-up stint heading up research for syndicated tabloid show Hard Copy, Colbert started a service that provided clients (news programs, talent agencies, studios) with leads on developable true-life stories. "There are these people called story brokers," CBS News president Susan Zirinsky once observed of such middlemen when she was executive producer of 48 Hours. "I have found some dealings with some of the brokers to be grotesque." Yet with Colbert, she emphasized at the time, "everything is above board."
His pipeline yielded dozens of discoveries, which were turned into feature films such as 1996's Fly Away Home and 2012's The Vow. He'd gotten the idea for the company after a news investigation he'd worked on, about a baby brokering ring, was turned into a 1994 movie on CBS starring Cybill Shepherd. (There was a Colbert stand-in with a mustache he still disproves of: "They made me look like Geraldo.") Chasing stranger-than-fiction tales of American life is deeply ingrained in his own life: He met his wife, Dawna, then a country-western singer, after she solved her mother's murder by finding evidence that identified her father as the culprit. That story was also dramatized by CBS, in 1997, as Deep Family Secrets.
Colbert entered the Coopersphere in 2011, when a source tipped him off that some cash discovered near an Oregon riverbank in 1980 was planted there in a scheme by the skyjacker to mislead authorities. Colbert pursued the lead to Rackstraw, at that point living in San Diego. Rackstraw fit the established FBI profile as well as any Cooper contender. It wasn't just that his old pictures looked reasonably like the sketch. While a soldier, he'd trained in demolition and parachuting, so he'd know how to make a bomb and jump out of a plane. He also had a potential motive, having at the time of the skyjacking only recently been kicked out of the Army for lying about finishing high school. Most tantalizing, the FBI had looked closely at him in the 1970s, when he'd had a series of run-ins with the law. At one point, he was charged with the murder of his stepfather — and acquitted. By 1979, while held on charges of check-kiting, possession of explosives and, of all things, theft of a small plane, he was asked in a TV interview about the rumor that he was Cooper. "Could have been," he wryly responded, "could have been." This verbal footsie had been his M.O. ever since.
Rackstraw spent the next several decades living a quiet life, although Colbert claims his inquiry found that, privately, he would brag to family members and friends that he was Cooper. Rackstraw's attorney has explained that if his client ever said such things they were wisecracks about his public reputation, not factual admissions.
Colbert advanced his theory over several years, assembling a body of clues with the help of dozens of retired police, military vets, former government lawyers and others he'd cultivated during his media career. They lent their expertise on a volunteer basis; he came to refer to them as his Cold Case Team. "I'd call them in their rowboats, on their golf courses, in their La-Z-Boys," he says. "My pitch was, 'I've found Cooper, I just need to nail him down.' "
In July 2016, three years after he ambushed Rackstraw, Colbert had amassed what he describes as 95 pieces of "physical, forensic, direct, testimonial, foundational, hearsay and documentary evidence." Unable to get his own documentary off the ground without Rackstraw's commitment, Colbert agreed to appear on a History Channel special about the Cooper phenomenon called D.B. Cooper: Case Closed? which followed former assistant FBI director Tom Fuentes as he sorted through a number of suspects who'd gained traction over the decades. Some of these men, and one woman — a recreational pilot and former Merchant Marine who had undergone one of Washington State's first gender reassignment surgeries in 1969 — had been fingered for the crime by self-appointed sleuths who, like Colbert, had dropped down their own rabbit holes.
The head of the FBI's Seattle Division announced on air that the FBI was done investigating — unless key physical evidence turned up. Meanwhile, the agent directly overseeing the Cooper case, Curtis Eng, explained that he'd reviewed the evidence independently amassed by Colbert and that "it didn't prove that his suspect was Dan Cooper." Late in the program, a stewardess who'd dealt most directly with the skyjacker was shown old photos and video of Rackstraw. She said she didn't recognize him as Cooper. Colbert was left wringing his hands, admitting that his case is ultimately circumstantial and — humiliatingly, since he saw himself as shepherding his own ad hoc law enforcement agency of professionals — denying that he's just another Cooperite obsessive.
Colbert's linked goals — proving that Rackstraw was Cooper and profiting from it by selling his project about the pursuit — had been foiled by the History Channel fiasco. But this wasn't something he was willing to accept. Colbert came to believe the FBI "bushwhacked" his team because they'd come close to proving that the bureau should've long ago brought a prosecutable case against Rackstraw. "I'm from the Reagan generation," Colbert says. "I've leaned conservative. I've always been a red, white and blue guy. I went in there, coat-and-tie, and suddenly the FBI is messing with us. I was naive."
Colbert and his crew — whose years of experience had been, Colbert felt, disrespected by the bureau — pursued multiple tracks. They discovered what they believed to be parts of the parachute in a remote area of eastern Washington State and turned the materials in to the bureau in 2017. Then, in 2018, after successfully suing the FBI to release much of its now-closed file, Cold Case Team member Rick Sherwood, who'd served in an intelligence unit during the Vietnam War, decrypted code in letters Cooper had sent to media outlets after the skyjacking, in which he'd apparently given away his identity.
According to Sherwood's cryptography, the results of which Colbert publicized, one decoded letter included the phrasing IF CATCH I AM CIA. Colbert contends he's established evidence that Rackstraw was a longtime CIA asset and now believes that collusion explains why the FBI stopped looking into him back in the 1970s as well as why, after the charade of keeping up an investigation for decades, it closed the case when his team grew too hot on its tail.
Colbert connected The Hollywood Reporter with multiple sources to back up his position. Ken Overturf was Rackstraw's Vietnam commander in late 1969, when Rackstraw was a helicopter pilot for an intelligence unit in the Army's 1st Cavalry Division. By Overturf's account, Rackstraw's demeanor along with security clearance issues ultimately led, by early 1970, to his exile to a less-sexy unit, flying maintenance support — "ash-and-trash missions." It was during these doldrums, at the Phuoc Vinh Base Camp near the border with Cambodia, that Rackstraw fell in with a man well known among the U.S. military there to be a CIA operative. Overturf remembers observing Rackstraw accompanying the agent twice out of Phuoc Vinh and not returning for several days.
Colbert also offered up Jim Christy, a former high-ranking official in the Air Force Office of Special Investigations, who had a contact float the Rackstraw theory by a CIA source: "He said, 'Listen very closely. We cannot confirm.' Usually the answer is, 'We cannot confirm or deny.' It was code, of 'yes.' "
Colbert insists "I don't do conspiracies." Yet since the embarrassment of the History special, he attributes his run of bad luck in advancing his work to a hidden hand — a "blackout" orchestrated by the FBI in collusion with the CIA attempting to shield Rackstraw.
By Colbert's logic, all of this explains the mere lip service Hollywood gatekeepers have subsequently paid to his pitch for a Rackstraw-is-Cooper co-production. Colbert cites his decades of experience fielding and vetting pitches in the news trenches to contend that, while he's used to hearing standard pass lines ("Wrong demo," "The boss isn't into it"), this is different. "When the arrows all start pointing in the same direction," he says, "my radar goes up." By February 2018, he'd grown so convinced that he held a press conference in front of the FBI's headquarters to announce that the bureau "has been covering up, stonewalling, and flat-out lying" about why Rackstraw was cleared in order to protect his decades of black-ops history with the CIA.
Michael London, Colbert's manager and a veteran of the unscripted TV space beginning with Unsolved Mysteries in the 1980s, backs him: "What I think is happening is that the production companies and channels that do these types of shows believe that in the future they'll need the cooperation of the FBI and they don't want to burn that bridge."
To bolster his theory, Colbert shares a seven-page document, one of many he'd sent to THR over a period of months. The dense timeline of what he terms the FBI "cover-up" is color-coded. ("BLUE notes efforts to quash related media stories or to mislead public; RED refers to secret or covered-up case facts," etc.) It tracks what he sees as an extensive alleged suppression campaign, from the J. Edgar Hoover era through the current administration of director Christopher A. Wray, with what Colbert deems an incriminating, or at least disquieting, accumulation of correspondence.
But an examination of Colbert's material reveals something more mundane: the normal indignities of Hollywood and media decision-making. Decades of frustration have transformed the soft no of a development executive from a banality to sinister intrigue.
There are no definitive answers inside the Coopersphere — only a disorienting fun house of doubt and bewilderment.
Given the mania that surrounds its solving, today the crime can now feel quaint. After all, nobody died. But Cooper's skyjacking long ago transcended an individual act to become an ever-expanding multiverse of tales — that most modern of Hollywood products.
Take that 2016 History doc, which caught the eye of a 30-something Alabama machinist who catfished (used a fake virtual identity to lure people online) in his spare time. He targeted Rackstraw on Facebook, posing as a 52-year-old nurse named Kelly Young. Then he contacted Colbert with the results of his inquiry: "I'm poor as dirt," the man wrote Colbert of his obsession with the hunt for Cooper. "This is all I do and study sir. I have no hobbies anymore, I'm addicted to the chase."
Though the machinist's relationship with Colbert proved short-lived because he, in an apparent attempt to better lure his mark, escalated to racier messages, his catfishing did yield fresh intelligence from Rackstraw about his own Cooper-related musings. It included Rackstraw speaking with authority about the river cash ("I could be wrong, but I believe that's all that will be found"), his own shadowy special-ops reputation ("Everything I did for our government raised questions"), his vexation with Colbert's crew ("what I'm concerned with is those assholes beating me to a movie") and his frustrated desire to finally take charge of his own life story by writing a film script about it. "I can't get started until the bills are paid," he typed to Kelly. "I'm already dead tired at the end of six day work weeks. … I am looking for a place (office, apartment whatever) to gather all of my stuff and write."
In mid-May, THR reached Rackstraw by phone. Rackstraw made it clear at the outset that he wouldn't speak about his connection to the Cooper saga — unless, that is, he was paid on terms to his liking. "I'm probably one of the only people who can close the case," he said. As for Hollywood interest in his story, he said that both WME and CAA had reached out, as well as other production companies whose names he couldn't recall. (THR has confirmed they included Magical Elves.) But by his own account, his own hard bargaining had scared them all away.
Rackstraw was most fired up about Colbert, whom he regarded as a mix of irritant, hellhound and sheer comic relief. Rackstraw said the catfishing was a Colbert-initiated operation, and detailed how he "reverse catfished him with the help of a couple of lesbians who live near where I work."
While Rackstraw had said he'd think over speaking further, THR heard from him only once more, a short while later. He emailed a warning of Colbert's "numerous attempts to dupe yet another media source," issuing a "formal notice and injunction" from publishing anything about him.
After Rackstraw's death in July, THR talked with his attorney, Dennis Roberts, who said that Colbert's investigation drove Rackstraw "nuts" and insisted "it's all bullshit. He's not D.B. Cooper." In Roberts' next breath, though, he said Rackstraw had been responsible for one of the many less-renowned copycat skyjackings that had followed Cooper's — and this is why his client never sued Colbert for defamation. "It would have meant that [Rackstraw] would have to admit the second skyjack. He would have opened himself to a deposition."
Roberts either wouldn't or couldn't provide the date of the other skyjacking, although he pinpointed it as between the date of the Cooper flight, Nov. 24, 1971, and that of another prominent suspect in the Coopersphere, Richard Floyd McCoy Jr., who was caught after bailing out of a Boeing 727 over Utah with $500,000 on April 7, 1972. Brendan I. Koerner, author of The Skies Belong to Us, a history of U.S. aircraft hijackings between 1961 and 1973, tells THR he doesn't know of any other unsolved cases aside from the Cooper incident. "That sounds highly implausible," he says. Colbert, later digesting Roberts' claim, is for once briefly at a loss for words: "I don't know where to start. He's carrying the water for a dead man."
As for the business with the CIA, Roberts says he doesn't know about it, except that Rackstraw did work in pre-revolution Iran as a pilot "teaching the Shah's people how to fly helicopters."
Maybe Rackstraw was a CIA asset. Maybe he hijacked another jet. Maybe he was in fact D.B. Cooper. Or maybe he was just another Cooperite obsessive who enjoyed being taken for an American antihero. More than one of these things could be true, or none of them. The only thing known for certain is that Colbert's quest has remade the way he understands the world.
When Colbert received word in July that Rackstraw had died, he turned into Paul Revere, alerting the press, staying on-message: "we absolutely believe he was Cooper." Media interest in his story spiked — "Fox News limo'd us in; Shep [Smith] did the interview" — including a spate of podcasters. Yet this post-passing period, in which Rackstraw is out of the mix, brings Colbert a new anxiety. He's now worried that some of Rackstraw's extended family members may be "trying to cash in with a tabloid or unethical moviemaker."
The perfect criminal eluded the law. But order can still be enforced on the D.B Cooper narrative. As with so many mysteries, truth is consigned to play out as entertainment. The Making a Murderer documentarians, who like other darlings of the new age of true crime have seen their own facts and ethics called into question, investigated Steven Avery for a decade before their work first aired on Netflix. For Tom Colbert, who's spent eight years and counting in the Coopersphere, the journey continues. He still believes — and he's still pitching.
A version of this story first appeared in the Sept. 4 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.