Robert November

Robert November was the very first person to step foot on the schooner Enterprise. He then turned around and told everyone else that it was safe to go in.
Eventually he got very old and by that point he finally was given the chance to be Captain. It was a sympathy promotion because he was still a mere Lieutenant C+ Grade after a lifetime in Starfleet.
His command of the Enterprise was so embarrassing and humiliating that nobody ever talks about it. In fact, years later when the Enterprise was going to be sold to Cyrano Smith and turned into a tribble hauler, Admiral Rudy Ray Moore conveniently forgot to inform the buyer that the ship had been turned inside out during November's command. The ship was never truly put back together properly, even by the "Irish Miracle Drinker".
Many at Starfleet, were surprised to see the ship make it home, after November's 5-week mission. The ship returned in 4 pieces. Saucer (now shaped like a square), towing the stardrive section, towing the two warp engines. The ship was somehow still able to go to warp speed and operate although literally in pieces.
The mystery intensified when the saucer section returned not shaped like a saucer, but a square. November explained that unlike other captains, he didn't cut any corners.
Oddly enough the saucer would turn into a square again, at the end of Captain Trout's 5-month mission. This time the ship was inhabited by an alien intelligence that morphed the saucer into the personality of the captain.
These fantastic feats led the accident prone November to be promoted to Commodore, but given the cautionary title "At Large and Dangerous" Lest he ever be taken seriously.
November then told Christopher Trout that it was okay for him to step foot on the Enterprise now. Trout did not take the Commodore seriously, wisely dismissing him as a dotty old coot. Trout later found out that the ship was undergoing a final baryon sweep and he would have been killed extremely painfully had he boarded.