When Flax was a child, Bok used his considerable wealth to gain the best and most expensive tutors for his son in the hopes that Flax would follow in his footsteps. Once Flax was old enough to join the Ferengi fleet, Bok continued to employ bribery to assure Flax' rapid rise up the chain of command. By the year 2355, Flax had been promoted to DaiMon and was assigned command of the scout, Seventy-Fifth Rule.
During a survey of the Maxia Zeta star system, the Seventy-Fifth Rule encountered the Federation Starfleet starship USS Stargazer, commanded by Captain Jean-Luc Picard. Flax launched an unprovoked attack on the Stargazer. Since the Ferengi had refused communications, it was not known to the Federation at the time that it was a Ferengi ship, nor was it known that it was Bok's son who was in command. Captain Picard used what would later be called the Picard Maneuver to defeat the Ferengi - destroying the Ferengi ship and killing Bok's son.
Shortly after, a starship commanded by Bok entered the system in search of the Seventy-Fifth Rule, but only the stricken Stargazer was found in decaying orbit of Maxia Zeta V. Against many of his crews wishes and risking trouble from his superiors, Bok took control of the Stargazer as a personal prize in the hopes of one day hatching a plot for revenge against Picard. (TNG episode: "The Battle"; TLE novel: The Buried Age)
It wasn't until 2364 that Bok was able to enact an elaborate scheme to take revenge upon Captain Picard and the Federation. Using thought makers, which were mind altering devices, Bok attempted to manipulate Picard into attacking his own ship. When Bok's first officer Kazago realized what was going on, Kazago relived Bok for engaging in an unprofitable venture. (TNG episode: "The Battle")
Following this, Bok was subsequently imprisoned. He was able to buy his freedom a few years later, and once again began plotting revenge against Picard. He acquired another starship and crew, along with a subspace transporter. Bok manipulated the DNA of Jason Vigo to make it appear that Vigo was Picard's son, and told Picard that Vigo was his son. Bok also informed Picard that he was going to kill the young man. This second attempt to take revenge was also unsuccessful once Picard told Bok's crew the truth about their leader - they also relieved Bok because there was no profit in what he was doing. (TNG episode: "Bloodlines")
In 2383, Bok was involved in an attempt to hijack the Earth Starfleet NX-class starship Intrepid. He planned to use the ancient ship to exploit the time travel potentials of the Split Infinite anomaly. Successfully capturing the ship with mercenaries that included Klingons, Nausicaans, and Breen, Bok held Geordi La Forge and several personnel from the USS Challenger prisoner as he attempted to carry out his plan. He also revealed that Berlinghoff Rasmussen, who was supposed to have been helping the Starfleet crew understand the Intrepid, was actually working for him. However, Bok and his accomplice Sloe died when the Intrepid slingshotted around the Split Inifinite and accidentally reached the Big Bang. (TNG novel: Indistinguishable from Magic)