In 2355, Bok's son had also risen to the rank of DaiMon and given command of a Ferengi starship. In the Maxia Zeta star system, that ship encountered the Federation starship USS Stargazer, commanded by Captain Jean-Luc Picard. Bok's son proceeded to launch an unprovoked attack on the Stargazer. The Ferengi had refused communications, it was not known 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.
Nine years later, in 2364 Bok found the Stargazer and hatched 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.
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 as though 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.