Character Analysis
Captain J.T. Esteban is the Milhouse of the Star Trek universe. Sorry, buddy, but you know it's true.
Esteban is the by-the-books Captain of the USS Grissom. He makes no decision unless it's within the rules…and he feels even more comfortable having Starfleet provide a permission slip first.
This characterization is evident the first time we meet him. Saavik and David request permission to beam up a mysterious life form detected on Genesis. Esteban directly quotes regulations to them, saying,
ESTEBAN: Nothing shall be beamed aboard until danger of contamination has been eliminated.
They manage to convince him to allow them to beam down to the planet to investigate but only after quoting a different rule to him. Dude likes his rules.
This personality makes Esteban an interesting foil to Admiral Kirk. Unlike Esteban, Kirk acts according to what he feels is necessary and morally right. Because he feels it's right to help Spock and McCoy, he disobeys Admiral Morrow's direct order to stay away from Genesis. The quest becomes Kirk's personal responsibility, and he puts his career and life on the line to see it through.
Esteban, on the other hand, seems to hide behind rules to skirt personal responsibility. When Saavik and David are on Genesis, he reminds them that the "landing is Captain's discretion, and [he's] the one who's out on a limb."
Ultimately, Esteban's ineffectual, timid ways cost both him and his crew dearly. When Saavik and David find Spock, they request to be beamed aboard the ship. Instead of ordering a grab and go, Esteban wishes to get instructions from Starfleet. This allows Kruge to get the jump on them, and the Klingon gunner accidentally destroys the Grissom.
Guess everything isn't coming up Milhouse today.