As we reach the 53rd anniversary of the only unsolved skyjacking in American history, the D.B. Cooper case remains a source of fascination for amateur sleuths and collectors alike.
Cooper infamously hijacked a Northwest Orient Airlines flight from Portland, Oregon, to Seattle on Nov. 24, 1971. He demanded $200,000 and four parachutes when the plane landed in Seattle and then took off another on another flight, reportedly bound for Mexico City.
Somewhere between Seattle and Portland, Cooper jumped from the plane and was never found — although some of the ransom money was discovered on the banks of the Columbia River in 1980.
A digital publication in Wyoming called the Cowboy State Daily spoke recently to aviation YouTuber Dan Gryder, who said a parachute found in the garage of suspect Richard McCoy has a "one in a billion" chance of not matching the parachute given to Cooper.
With Cooper again trending on Twitter and the annual Thanksgiving mystery still being debated, cllct decided to run down our list of the 10 most collectible criminals of all time.
1. Billy The Kid
This will be a shocker to many. Billy the Kid at No. 1? An outlaw who died in 1881?
Well, that's actually part of the reason he's ranked here. Any item from the gunslinger, who supposedly killed 21 people before he was 21 (the year he died), is extremely rare. In fact, the original plate of a picture of him taken in 1880 was bought by the Koch Brothers for $2.3 million.
In 2021, the gun used to kill the man who was named William H. Bonney sold for $6 million at Bonhams, the record price paid for any firearm.
2. Al Capone
There are many Capone items on the market, but that hasn't stopped collectors from spending a lot of money on the notorious gangster.
In 2021, Witherall's hosted Capone's estate sale, and the numbers were outrageous. His favorite .45 pistol sold for $860,000. His Patek Phillipe pocket watch sold for $190,000. His cigar humidor sold for $120,000. And his diamond pocket knife sold for $65,000.
Capone's gold coin, bank interest notes have become plentiful in the market. They are guaranteed to do $20,000 every time.
3. Bonnie and Clyde
Bonnie Parker and Clyde Barrow are infamous for their near two-year crime spree robbing banks, restaurants and gas stations across Texas, Oklahoma, Missouri and New Mexico. The two were shot and and killed in Louisiana in May 1934.
The pair are known thanks in part to the 1967 film starring Warren Beatty and Faye Dunaway, a 2013 TV miniseries and the 2019 film "The Highwaymen" with Kevin Costner and Woody Harrelson.
Big ticket items from the couple have sold in recent years. In 1973, their 1934 Ford — the car they died in, which was rife with bullet holes — sold for $175,000.
RR Auctions has sold four guns — Barrow's 1911 Colt .45 ($240,000), Parker's .38-caliber Detective Special ($264,000) that was taped to her thigh when she was killed, a Barrow sawed off shotgun ($68,750) and a Barrow revolver ($32,750). The Bulova watch worn by Barrow when he was killed sold for $112,500.
4. John Dillinger
Dillinger was robbing banks and killing people during the same era as Bonnie and Clyde. He achieved his infamous status from his jailbreak in Indiana, where he used a wooden gun and stole a sheriff's car to escape. He then became America's Public Enemy No. 1.
The wooden gun sold for $75,313, and the stolen 1933 Ford V-8 sold for $149,788. Dillinger was killed a month later in Chicago outside a movie theatre.
5. Bugsy Siegel
The mobster who helped build Las Vegas, as captured in the 1991 film starring Beatty, has had some outrageous items sell at auction, including the document that signed over the Flamingo hotel to him, which sold for $52,500 in May 2021 at Heritage Auctions. Another document signed by the mobster sold for $45,000. Also sought-after are the highest domination chips from the Flamingo while it was under Siegel's control.
A handwritten letter to Siegel's wife sold at Julien's in 2022 for $38,400, and a home movie reel sold for $28,800. The $100 chip from 1947, of which there are roughly 20 specimens known, typically sell for $15,000 to $20,000. Due to the hotel's financial problems, Siegel was killed by an unknown person in June 1947.
6. Lee Harvey Oswald
The most infamous assassin in history has plenty of collectibles associated with him — though a large population of collectors shy away from Oswald items for obvious reasons.
The most well-known piece is probably the check made out to "Miss Lee Harvey Oswald" from the Texas Book Depository — the building from which Oswald allegedly shot President John F. Kennedy — paying him for his three days of work in November 1963. It sold in 2013 for $21,250 at Heritage in 2013 and again in 2020 for $69,000.
There's also a surprising amount of documents available from Oswald, which sell from between $3,000 and $10,000 individually. The most polarizing piece? His Marine Corps Rifle Score Book, which sold for $20,315 in 2008.
7. Pablo Escobar
In more recent years, some of the items from the life of the "King of Cocaine" have escaped Colombia, mostly because people in his inner circle saw the prices Escobar items were commanding in America.
Escobar, the head of the Medellin cartel, has also experienced a rise in notoriety due to television, namely ESPN's "30 for 30" documentary "The Two Escobars" (2010) and the Netflix drama "Narcos" (2015-17).
Escobar items are still very rare, and recent lots at Goldin Auctions suggest how valuable they are. The will of Escobar, who was killed at 44 in 1993, sold earlier this month for $52,460. A very limited edition book, signed by Escobar and family members, currently has a bid of $31,720 with three days remaining in the auction.
8. D.B. Cooper
No criminal has been the subject of more documentaries in the last five years than D.B. Cooper. The amount of people who know the half-century old story has increased exponentially.
Unfortunately for collectors, there is not much to collect, which starts with the fact we don't know who Cooper really was. The only thing collectible is the dollar bills that matched to the FBI logging of the ransom money, which was found by 8-year-old Brian Ingram in 1980.
Ingram found pieces of $5,800 out of the $200,000 Cooper was given. He was allowed to keep some of it and, in 2008, brought it to Heritage to auction. The best piece sold for $5,975. Over time, the popularity of the notes has increased. The last piece that sold, in September, was bought for $20,400.
Replica D.B. Cooper "Wanted" posters are popular, but you'll never see real ones. They were never made.
9. Mark David Chapman
Few items have sold surrounding John Lennon's assassin, but one collector paid $990,000 at Goldin Auctions for the "Double Fantasy" album Chapman had Lennon sign for him hours before he killed him. That is still the highest price ever paid for a vinyl album.
Other Chapman items, such as the drug test New York police gave him and a hotel bill have surfaced. They sell in the $1,000 range.
10. Jack Ruby
Ruby shot Oswald on live television, and several items from that shocking moment have hit the market. The gun he used in the murder sold for $220,000 in 1991. The fedora he was wearing sold for $53,000 in 2009.
Other high-priced items include his original finger prints ($51,600) and the TV camera that shot the scene ($19,680).
Darren Rovell is the founder of cllct.com and one of the country's leading reporters on the collectibles market. He previously worked for ESPN, CNBC and The Action Network.