
Kirk- I think he admired Kirks never say die attitude. They where both leaders and both lived full lives. While Sisko followed the rules a bit more like Kirk he knew when to bend them. I think they are both the same because as I said they lived their lives to the full and knew when to bring out the fists.

Picard- I always found Picard a little too perfect. Anytime he had a moral dilemma he would angst about it a bit then some techno thing would come along and he would get to have his cake and eat it too. Then he would give a condesending speech how humans would be lowly like unevolved alien of the week but they got better. That got old real fast.
That being said I always thought that Picard represented the dream and Sisko defended the reality.
You want someone to represent the best and brightest of the Federation you got Picard.
You want someone to keep the Federation alive by fighting in the trenches and relying on any and all means you got Sisko.

Janeway.
She got her crew lost and a few of them killed in the Delta quadrandt. Sisko whould have gotten them home sooner. Sisko was very goal oriented , you did not want to get between Sisko and his target.

Archer
Good lord, what an idiot.
I mean so many ways to describe Captain 'Wah stop holding us back Vulcan meanies' Archer.
Bully, dumb ass, childish.
He took his Ship to seek out new life and ended up pissing off most of the new life he found. For someone who just arrived on the Galatic stage he spent most of the time passing judgement left right and centre.
Sisko was a better diplomat and commander in so many ways.