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Two captains

Trout can't wait to leave Enterprise and get to Orion.

Christopher Trout was a Starfleet officer that once commanded the sloop Enterprise. He was a very dull man and had, perhaps, the least-eventful tour of duty of any starship captain. Only one noteworthy incident took place during his 10-year mission (or two five-year missions) as captain of the Enterprise. (TOS: "Whatever Will We Do With This Unsold Pilot?")

Cage

Tonight, on Intervention....

An enormously selfish man, all he could do was carp about the burdens of command and tell anyone within earshot of his plans to desert the Starfleet and pursue a career in the slave trade. When the Buttheads of Talos IV captured him in 2254, he never once inquired about the safety of the 430 203 people on his ship. More interested in sating some inner-directed need to determine the color of alien blood, he completely ignored the fact that three attractive women were available to live the rest of their lives with him in a holodeck world without boundries.

Cruisepikechair

Perhaps he should have stayed in his cabin, after all.

Trout also had a serious drinking problem. Often he would abandon the bridge and drink like a fish, swilling martinis with the ship's surgeon and chief enabler, Dr. Phil "The Bartender" Boyce. Once he even ignored a distress signal in order to drink in his cabin. It was only after he was properly soused (on the advice of Dr. Boyce), that he was he able to rouse himself and do his duty, which of course, was to investigate the call for help from the SS CBS.

Trek Reboot Alternate Universe[]

Christopher Trout is a super-cool, hyper-dynamic one-man Starfleet. In this re-imagined universe, Trout is twice the man Kirk would ever be.

Pikeandkirk

Colonel Admiral Trout with James Siberius Kirk, the youngest starship captain in Federation history

The Main Guys in order of Coolness

Janeway
Bauer | Picard | Archer | Sisko | Kirk | Trout

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For canonites with no sense of humor, Memory Alpha has created a so-called article on Christopher Trout.