Jake is introduced as an adolescent, played by Thomas Hobson, who moves to the Deep Space Nine station three years after the death of his mother aboard USS Saratoga in the Battle of Wolf 359.

He briefly dated a Bajoran dabo girl named Mardah against his father's wishes, who embarrasses Jake by revealing his penchant for dom-jot hustling and poetry.

In 2372, Jake wrote a draft of his first novel, Anslem, under the influence of Onaya, an alluring alien woman who feeds on creative neural energy by tactile absorption through the cranium ("The Muse").

In an alternate timeline ("The Visitor"), Benjamin Sisko is thrust into an odd sub-space dimension after being struck by an errant energy bolt in the USS Defiant engine room.

[3] Jake introduces his father to freighter captain Kasidy Yates, with whom Benjamin becomes romantically involved and marries in the final months of the Dominion War.