The Brothers of Trouble were a religious order that arose out of the Trouble Boys in a distant, post-apocalyptic future. They believed the 20th-century hero Jack-in-the-Box to be a prophet and devoted themselves to preserving his legacy, but badly misunderstood him to be a grim vigilante rather than a crime-fighting clown. This misconception caused them to track down and kidnap Jerome Johnson, the son of the second Jack and transform him into the fanatical Jackson, who they then sent back in time to ensure that their future came to pass.

Following the Jackson's defeat and Zachary Johnson's decision to retire from vigilanteism, it is unclear whether the Brothers of Trouble will ever exist, or whether the future from which they hailed still even exists.

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