Captain LamoSoft
Kirk and Picard are legends because we've followed them along their journeys on the Enterprise and seen what they've made of situations thrown at them. They got the job done, at least most of the time (and never mind the occasional stray from the Prime Directive). We've also seen other captains, commodores, and admirals within the fleet that everyone can respect for their command presence: Sulu, Robau, Spock, Pike, Garrett, Decker, Jellico, Satie, Nechayev, etc.. If you crossed any of them, they'd relieve you from duty and send you to your quarters without dinner.
And then you have other individuals of various command grade who, when you saw them in action, always thought to yourself, "...and just how did they achieve their rank?" Of course, everyone has different management styles, but sometimes you end up with a boss at work who you initially think is incapable at leading the team ... and eventually you're proven correct.
Captain J.T. Esteban, U.S.S. Grissom
In the third Star Trek movie, we were introduced to a new Starfleet vessel class with a unique look. It was a nice departure from seeing yet another ship that looked just like the Enterprise but with a different name. This gave me confidence that the fleet did indeed have different classes of ships for different purposes.
Captain Esteban was pretty much a by-the-book type due to the sensitivity of the nature surrounding the Genesis planet. Fine, I understand this. And sure, the Grissom is not a ship built for combat. Anyone can see that. But anyone can also see that this captain isn't exactly lightening-quick on the shields and tactics button. If you see an enemy ship declocking behind you, that's a hint-and-a-half and you turn on the afterburners and put some distance between you and your threat. Don't stand there thinking, "Oh my God!"


Either the Klingon's torpedo is really, really powerful, the Grissom has a hull as weak as an eggshell, or the commanding officer in charge needs to do the Kirk thing with an immediate, "Full shields, emergency hard to starboard, return fire!" Otherwise, Starfleet needs to send some of its captains to training classes specializing in hardcore combat tactics.
Commodore Stocker, U.S.S. Enterprise
I'm being a little unfair here because Commodore Stocker isn't trained for starship command. He's intended to run a starbase. And in "The Deadly Years" he was a in a tight situation where the entire senior staff of the ship was in a time-sensitive circumstance that removed their ability to command the ship. But any time you have a scenario where you're going to hold the reigns and pull some stunts ... like crossing the neutral zone ... you'd better be up to chops and able to make decisions at critical moments. Good captains can improvise and adapt:

Not this guy.
Note to any bridge crew: if you have a commanding officer who is unfamiliar with the capabilities of the ship and you're in a possible lose-everything scenario, you grab the nearest blunt object and hit him over the head. Then you do what you have to do to get the ship out of harms way or blow the ship up to prevent the enemy from gaining internal secrets. As soon as he fearfully utters the words, "What am I going to do?" - that's your queue.
Commander Hutchinson, Arkaria Base
With a name like Calvin, you're almost guaranteed to automatically lack respect by your peers. While his responsibilities may not include the administration of a starship's operations, a role in Starfleet's command crew in some remote location is still a huge responsibility, even though it may occasionally include light duties like picking out the right color scheme for certain guest lounges on the base.

Could you hold a guy with a face like this in high-esteem, seriously? His motor-mouth isn't conducive to long-term command respect because after some time anyone in his staff is eventually going to tune him out.
Captain John Harriman, U.S.S. Enterprise (B)
After seeing the opening scene of "Generations," I was hoping Ferris Bueller would rush in from the turbolift to save the day.

Watching his performance in the center seat didn't exactly aspire me to believe that every captain in the fleet is of high caliber. Sure, the script required that there be a noticeable difference between the maturity of Kirk's experience and get-things-done attitude and this new guy, but it's astonishing that Starfleet would hand over the Enterprise-B to someone with a super play-it-safe sensibility.
Maybe there was a shortage of potential captains around this time, or perhaps Harriman was well-connected to get a shot at the big chair... who knows. All that's for sure is that if Kirk wasn't on the bridge when the Nexus was wreaking havoc on the transport ships, nobody would've been saved and the movie wouldn't have happened ... which probably wouldn't have been such a bad thing, although there would be no Guinan in the 24th century.