Mr. Boothby is the curmudgeonly groundskeeper at Starfleet Academy in San Francisco on Earth. He was born in the mid to late 23rd century. (TNG: "The First Duty") He has been working at Starfleet Academy since about 2319 and has seen a lot of promising young cadets come and go, often offering up helpful advice and kind words; among them such prominent Starfleet captains as Jean-Luc Picard, Kathryn Janeway, Richardson, and Lopez. (VOY: "In the Flesh")
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. (TNG: "The First Duty")
Picard considered Boothby one of the wisest men he ever knew. (TNG: "Final Mission") 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. (TNG: "The Game") Boothby had more faith in Picard than Picard had in himself. The only thing Picard did which suprised Boothby was pinning a Ligonian within the first fourteen seconds of a wrestling match. At some point, Picard made some sort of 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. (TNG: "The First Duty")
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. (VOY: "The Fight")
Jean-Luc Picard advised Wesley Crusher to seek out Boothby when he was accepted to the Academy in 2367. (TNG: "Final Mission") Crusher met Boothby his first week there, and he took Crusher on the same tour Picard received forty years prior. He did not remember Picard at first, but his memory was later jogged and he told Wesley that he was proud of the captain's accomplishments. (TNG: "The Game") Boothby knew all of the Nova Squadron members and realized how much the other cadets revered them. He was shaken by the accident which claimed the life of Cadet Joshua Albert.
In 2368, Picard visited Boothby following the accident. Boothby recognized Picard immediately, and wondered what happened to his hair. At this time, Picard tried to express his appreciation for his advice and guilt over never showing his thanks, but Boothby dismissed his remorse. Boothby also explained to Picard how the other cadets treated Nova Squadron with godlike respect and how Nova Squadron wanted to maintain that image, leading Picard to realize that Cadet Nicholas Locarno may have planned an unorthodox stunt leading to the accident. Starship Enterprise-D personnel learned that Nova Squadron was attempting a Kolvoord Starburst. Picard's experience with Boothby was echoed when he confronted Cadet Crusher with the news and threatened to go to the board of inquiry, but Crusher realized he needed to tell the truth himself. (TNG: "The First Duty")
In 2375, Species 8472 established a training facility somewhere in the Delta Quadrant, recreating Starfleet Command, Starfleet Medical, and Starfleet Academy in perfect detail. They intended to instruct members of their species to act as humans and other Alpha Quadrant species in order to infiltrate the Federation, which they saw as a threat to their existence. The leader of the group took on the role of Boothby, and met Commander Chakotay of Voyager when he transported aboard the facility to investigate it. Captain Janeway later negotiated a cease-fire with the Boothby replicant, where Species 8472 would receive information about the nanoprobe weaponry and the Starfleet crew would be allowed to inspect Species 8472 technology and visit their simulation of Earth. (VOY: "In the Flesh")