Jack "Captain Hindsight" Brollin is a superhero who "helps" people in need by appearing at the scene to lecture them about what they did wrong to get into a certain accident and what methods they could have used to avoid it, instead of actually rescuing them. Despite this, civilians still feel much better afterwards. He is later framed for having sex with Courtney Love, however the pictures were actually of Butters in disguise and a hobo with Captain Hindsight's face Photoshopped onto it. Partly because of this, but also due to the constant pressure he felt, he removed his special ability through the machine he gained it from in Mysterion Rises, and went back to work as a news reporter again. He was personally invited to superheroes group Coon and Friends by Cartman, but he refused to join.
Captain Hindsight is the only superhero in South Park to wear an actual, typical superhero costume, which is not made up of other mix-matched clothes. His hair is black with a single curl on his forehead, whilst his head is shaped closer to a regular person’s than the rest of the cast, with a slight cleft chin. He wears a yellow base suit, with red briefs over it, which has a black H emblazoned on his chest, with a blue eye above it. Around his waist is a plain red belt, with a red buckle. He covers his hands and feet with a pair of matching gloves and boots, as well as adorning a red cape, which bears his symbol on the back. Overall, his appearance is very similar to Superman's, with yellow replacing blue and a different symbol.
As Jack Brolin, he wears a blue jacket and matching pants, with a white shirt complete with tie, due to his career as a reporter, another allusion to Superman.
Perfect 20/20 hindsight is the power that Captain Hindsight is most associated with. With his natural hindsight abilities raised to superhuman levels, due to an accident with a retroactive spider, Captain Hindsight can immediately know how an event could have been avoided just by looking at the scene. As it is perfect hindsight, it may give him knowledge that he didn't already have, such as building designs, to work. However, this power appears to force him to know how things could have been stopped and express it vocally, as he is seen muttering to himself when he was talking to Mysterion, leading him to label it as a curse as he can't save the people anyway. The greatest weakness to this power as Hindsight demonstrated, is the fact the ability only works after the action has occurred, which more often than not makes him regret doing the action in the first place and second guesses every action he does.
His only known, typical superpower, Captain Hindsight adopts a Superman pose as he flies. He appears to be able to move at superhuman speeds, as he is able to appear at catastrophes shortly after they happen.
It is also revealed he has shmoo-like sidekicks named Shoulda, Woulda, and Coulda (all references to his Hindsight ability); however none of them had made an appearance or was even mentioned during the actual events of the episodes beyond that first introduction. So what they are capable of or what they even are is never revealed.
|Minor Characters from Season Fourteen|
| Billy Miller | Billy Thompson | Captain Hindsight | Colonel Sanders | Grandma Marsh | Geoff Hamill | Justin Bieber | Kardashians | Kip Drordy | Matthew Broderick | Matt Lauer | Morgan Freeman | Mr. Yelman | Patty Hamill | Sarah Jessica Parker | Snooki | Tiger Woods | Tony Hayward | Woodsy Owl|