Groundskeeper at Starfleet Headquarters and Starfleet Academy on Earth, something of a fixture there since 2321. His career there has spanned more than half a century, during which his mentoring of numerous promising cadets has belied his apparently humble role as groundskeeper. Some of those whom Boothby has taken under his wing include Jean-Luc Picard, Captain Lopez, Captain Richardson, Valerie Archer and Kathryn Janeway. In fact, when Janeway was an academy cadet, groundskeeper Boothby used to give her fresh roses for her quarters.

When Jean-Luc Picard was a cadet in the 2320s, he regarded the irascible Boothby as "a mean-spirited, vicious old man." Boothby nevertheless helped guide Picard through a particularly difficult time when the young cadet had committed a serious offense. Boothby later recalled that he had simply helped Picard listen to himself. Boothby, for his part, followed Picard's career with some satisfaction. Years later, Picard came to understand Boothby more clearly, and regarded the old groundskeeper as one of the wisest men he had ever known. When Wesley Crusher entered Starfleet Academy in 2367, Picard advised him to seek out Boothby's advice.

Boothby was re-created in an elaborate simulation of Starfleet Command in the Delta Quadrant in 2375, when Species 8472 was preparing for an extensive intelligence-gathering operation against the Federation. The being portraying Boothby was agreeable to Captain Janeway's overtures of peace, ending the species' infiltration plans. Even though it was not the real Boothby, his portrayal of the groundskeeper's personality was so faithful that Janeway's encounter with him felt like a reunion with her old mentor.