Of all the many deaths in Prison Break season 5, Whip’s was the most tragic. Despite Michael Schofield’s apparent death in the 2009 TV movie Prison Break: The Final Break, the season 5 revival showed he was, in fact, alive and well but incarcerated in a prison in Yemen. Set seven years after the events of the TV movie, Prison Break season 5 featured a complicated plot with several twists and turns. Eventually, it was revealed Michael’s predicament was an elaborate scheme hatched by crooked CIA operative Jacob (Mark Feuerstein), who shacked up with his wife Sara (Sarah Wayne Callies) to frame Michael for murder and do away with him once and for all.
Alongside Michael and Sara, season 5 saw the return of several other original Prison Break characters including Michael’s brother Lincoln (Dominic Purcell), C-Note (Rockmond Dunbar) and T-Bag (Robert Knepper). There were new faces too like Whip (Augustus Prew) who Michael recruited from a prison to work with him on an undercover CIA project that involved them breaking out of prisons in Myanmar, Egypt, and Colombia.
Towards the end of the fifth season of Prison Break Whip was revealed to be more than just some random recruit. After he and Michael made it back from Yemen to American soil, Michael sent Whip on a mini-mission to Chicago. There, Whip was met by T-Bag who for some reason knew his real name, David Martin. In a shocking twist, it was revealed Whip was none other than T-Bag’s son – the product of a tryst in the early 1990s with a waitress in West Virginia. Apparently, Michael had hired Whip because he knew he’d inherited his father’s skills and would be a useful ally.
Tragically, in the season 5 finale of Prison Break Whip was shot in the stomach by Jacob’s henchwoman A&W (Marina Benedict) in a showdown between Michael and Jacob. Whip sadly died in the arms of the father he’d only just met after which T-Bag brutally took out his killer A&W by snapping her neck with his bare hands. T-Bag was then arrested by the FBI and sent back to where it all began - the Fox River State Penitentiary.
As sad as Whip’s Prison Break death was, T-Bag got to avenge his death properly when it turns out his new cellmate at Fox River is none other than Jacob. Prison Break’s season 5 finale ends with the camera panning out to the tune of Jacob’s screams as T-Bag exacts brutal revenge for his part in Whip’s death.