As I have stated before when writing these lists, someone always has to have the dubious honor of occupying the #5 spot, and this time that honor goes to the Captain of Deep Space nine, Benjamin Sisko. Now am I saying that Sisko is a bad captain, absolutely not.
Sisko masterfully handled the responsibilities of commanding a newly reformed space station, was very skilled in diplomacy, inspired loyalty in all those under his command, and did all this while balancing the home life of a recent widower and father of a teenage son.
Sisko had to find ways to try and please everyone, including upholding the values and regulations of Starfleet, while maintaining a level of peaceful existence with the different races and factions that inhabited DS9 and its surrounding planets such as Bajor.
All that being said, Sisko also showed on numerous occasions that, while he may not have been wild about it, he could make peace with engaging in somewhat shady and sometimes outright nefarious activities in order to achieve his goals, demonstrating that he didn’t mind bending the rules, if the ends justified the means, as I explored extensively in my piece regarding his actions in the episode “In the Pale Moonlight.”
Not only did Sisko explore the grey areas of Starfleet, at times he struggled to balance his duties as a Starfleet captain along with his duties as the Emissary, as they were perceived by the Bajorans. I am fully aware that the latter was a title that Sisko never asked for or even wanted at first, but were I a resident of DS9, I would feel somewhat uncomfortable being under the command of a captain who is willing to explore ways to carry out his objectives that might not be entirely ethical, moral, or even lawful, and seemed distracted at times trying to balance his roles as a Captain of a space station and a religious figure.
For those reasons, while I truly do like Captain Benjamin Sisko, he must fall to #5 on my list.