Bob Massingbird was the most brilliant legal mind in all of England. He once got a killer freed (and knighted in the New Year's Honours list), even though the man had been seen committing the murder by 13 witnesses, held the murder weapon in his hand and told arresting officers: "I'm glad I killed the bastard" indicating that he was clearly guilty. The family of the victim was even forced to pay to have the blood washed out of the killer's jacket. Massingbird also got Oscar Wilde convicted for acts of homosexuality, despite hard evidence of Wilde's heterosexuality.
Captain Edmund Blackadder chose to contact Massingbird, when he was facing a court-martial. However, Private Baldrick mixed up the letter to Massingbird with another, resulting in Massingbird being sent a letter from Captain Blackadder, asking for a sponge bag, while the other letter asking for legal advice ended up with George. Afterward Massingbird did send Blackadder a sponge bag.
- It is unknown if he is related to Sir Hugh Massingbird-Massingbird.