
The series takes place in an alternate 1930s history created by Weisman and McCoy. In this alternate timeline, the United States has fallen, and air travel has become the dominant form of transportation across North America, allowing air pirates to flourish in the world of Crimson Skies. When explaining the concept behind Crimson Skies, Jordan Weisman said he aimed to "take the concept of 16th-century Caribbean piracy and adapt it to a 1930s American setting."
In 1937, Nathan Zachary and the Fortune Hunters were recovering from the treacherous betrayal of Lucas Miles in the skies above Cuba by seeking the lost treasure of Sir Francis Drake. Finding Drake's Gold, the Fortune Hunters uncovered signs of British interest in Hawaii and were ambushed by the Medusas. Though victorious, the Fortune Hunters were puzzled by the British presence. Capturing a British Balmoral led them to a hidden British base, which they swiftly dismantled. Repelling a counterattack from HMS Barracuda, the Fortune Hunters used the British facilities and Drake's Gold to repair the Pandora, despite a final push from the Royal Air Force. Celebrating their newfound riches, the Fortune Hunters called off their party when they received a distress signal from an old friend—Ilsa Fassenbiender, daughter of Doctor Wilhelm Fassenbiender, who contacted them with news that her father had been seized by the Soviet secret police, while she was held captive by Boeing Aviation in Pacifica. The Fortune Hunters launched an attack on the CCCP airship Workers' Voyage to rescue the doctor, during which Nathan Zachary reunited with his former love, the Black Swan. Their airborne rescue successful, the Fortune Hunters attempted a similar feat with a surprise raid on the Boeing plant, aiming to free Ilsa and steal the prototype Hughes Bloodhawk, Blue Streak. Again successful, the Fortune Hunters were forced to strike the USSR once more—this time targeting a fuel tanker off the coast of Pacifica to refuel the Pandora. Returning to Pacifica, the Fortune Hunters launched a preemptive strike on a zeppelin belonging to Blake Aviation Security, which was a complete success. Not long after this triumph, the Fortune Hunters faced a new adversary. The previously unknown pirate group, the Black Hats, had downed the Workers' Voyage, an act that might not have been possible without the Fortune Hunters' destruction of its escorts. Overcome with guilt, the Fortune Hunters descended on the wreckage, repelling the Black Hats and ensuring the hospital ship could rescue the survivors. Euphoric from their victories and with two of the world’s top aircraft designers now on their side, the Fortune Hunters journeyed south to the Nation of Hollywood. Their initial goal was to free a movie star trapped by her contract, but they followed one successful rescue with another, stealing the world’s largest airplane and joining the first Johnson Cup Race, which Nathan Zachary won by a wide margin. This victory, on Johnny Johnson’s home ground, drove him to plot a sinister scheme to eliminate Zachary. When that failed, he used the race's distraction to send a Hughes Aviation combat zeppelin to destroy the Pandora. The attack destroyed the Hughes zeppelin, but left the Pandora severely damaged. Forced to flee inland, the Fortune Hunters hijacked the cargo zeppelin Figaro to tow the Pandora. Arriving in Sky Haven, the Fortune Hunters met up with the Black Swan and her crew. Both sides willing to put the past behind them, the night stretched late into the hours. The next morning, however, Zachary awoke to find his crew missing, with only the Black Swan as an ally, whose crew had also vanished. Searching the area around Sky Haven, Zachary intercepted a transmission from Sparks, the Pandora’s pilot. He was aboard the Rocky Express. Zachary rushed to his aid, but the Express was attacked by the Black Hats. The Express was escorted by Hellhounds from Sacred Trust Incorporated… who were expecting the Black Hats. Zachary and the Black Swan drove off both the pirates and the supposed security, disabled the Express' defenses, and rescued Sparks just before the locomotive exploded. Convinced the Black Hats were responsible for the disappearance of their crews, Zachary and the Black Swan set out to hunt down a leader of the Black Hats—Ulysses Boothe. Capturing Boothe, Zachary proposed a trade: Boothe for the return of the crews. Enraged but with no choice, Boothe agreed. Zachary dropped Boothe at the agreed location, only to be told the crews were being held in a cargo zeppelin wired with explosives. With expert precision, Zachary shot the zeppelin free, boarded it, and freed the crews. While the crews escaped, the Black Swan was shot down and captured on the ground. Together, the Fortune Hunters and the Black Swan proceeded to dismantle the Black Hats' operations in Sky Haven, culminating in the complete destruction of their mountain base, the theft of dozens of aerial torpedoes, and the rescue of the Black Swan. Realizing there had to be a secret alliance between the Black Hats and Sacred Trust, Zachary turned to the one man who might help them—Paladin Blake. Initially skeptical, Blake was eventually convinced of Zachary's sincerity and joined the Fortune Hunters in their campaign to eliminate both the Black Hats and Sacred Trust. Heading for the Sacred Trust HQ in Manhattan, Zachary contacted an old friend who led him to a Sacred Trust warehouse filled with contraband, being loaded onto a German freighter. Destroying the warehouse and the freighter, Zachary drew official attention to Sacred Trust's illegal activities. But the Fortune Hunters needed more proof. Proof that Waldo Carney, Sacred Trust’s accountant, was trying to flee the city. When his zeppelin was attacked by the Black Hats, the Fortune Hunters rescued him and delivered him safely to police headquarters. With their secrets exposed, Sacred Trust attempted to flee, loading their remaining contraband and documents onto zeppelins. However, the Fortune Hunters and Blake Aviation Security disabled the zeppelins, including the stolen Spruce Goose, and stopped Sacred Trust from escaping with the critical evidence. Furious at these repeated setbacks, the true mastermind behind both the Black Hats and Sacred Trust revealed himself—Lucas Miles, the man who had betrayed the Fortune Hunters in Cuba. In his massive zeppelin Dante, Miles tried to escape, but his airship and fighters were no match for the combined might of the Fortune Hunters and Blake Aviation Security. The Dante was shot down, and Miles was killed. Victorious once more, the Fortune Hunters accepted a generous reward from the government of the Empire State and decided to take a tropical break to enjoy it. Sea Haven is always a great place this time of year...
| PC | September 17, 2000 |
| Arcade | December 31, 2002 |