Mr. Boothby was the curmudgeonly groundskeeper at Starfleet Academy in San Francisco on Earth. He was born about the 2260s. He worked at Starfleet Academy from about 2321 and saw many promising young cadets come and go, often offering up helpful advice and kind words, among them such prominent Starfleet captains as Picard , Janeway , Richardson, and Lopez.
Boothby was disdainful of herbicides and other high-tech devices, and preferred to tend to the grounds by hand. After a big parrises squares win in 2324, it took Boothby three weeks to repair the grounds following the celebration. In 2368, Boothby claimed that he was cranky because he had been forced to replant the same flower bed several times.
Picard considered Boothby one of the wisest men he ever knew. Boothby gave Picard a grand tour of the grounds following his arrival at the Academy. Boothby once caught Picard carving the initials A.F. into his prized elm tree. Boothby had more faith in Picard than Picard had in himself. The only thing Picard did which surprised Boothby was pinning a Ligonian within the first fourteen seconds of a wrestling match. At some point, Picard made some mistake which jeopardized his Academy career. Had it not been for Boothby's advice to make the right decision, he might never have graduated. Boothby's suggestion was apparently met with resistance by Picard, and for a time, Picard considered Boothby a vicious and mean-spirited old man and did not speak to him for months. Boothby knew Picard needed to find his bearings. Picard never told Boothby how much he appreciated his help, but Boothby claimed Picard's noteworthy Starfleet career was repayment enough.
During Chakotay's stay at the Academy in the late 2340s, Boothby served as his boxing coach. A holographic recreation of Boothby was part of his training simulations aboard the USS Voyager .