|Seen||"The Prince and the Rebel"|
|Relationships||John Tucker (brother)|
|Job||Assistant to Prince Alfred|
Jennings was part of a plot to kidnap and hold Prince Alfred captive in Toronto. The price of the Prince's safe return was Ireland's freedom. During the course of the plot, Jennings murdered his own brother to throw the police off track. When Constable Henry Higgins was placed as the Prince's decoy for his public appearance, Jennings kidnapped both the Prince and Detective William Murdoch when they were left alone in the hotel room.
Jennings was a violent man. He hit the Prince several times while his Highness was a captive. However, the Toronto Constabulary tracked down the Brotherhood's hideout. Jennings believed they had a snitch and started threatening several of his cohorts. He also planned on burning down the barn to kill the Prince. When Eddie Cullen protested, Jennings ordered him to prove his loyalty to the Irish cause by killing Murdoch, Cullen instead shot Jennings in the stomach. Jennings' remains were presumably burned in the resulting fire.