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I'd work with this, you have a great idea going, but I'd make another pass at this or two.
I have to say, when I saw the title I thought it was going to be a shirt based off of "Captain Kirk is Climbing a Mountain" :P
You've set yourself a tricky task. What you've got here is a good first draft. If you can get the faces just right using a little more detail, while keeping it in the simple outline and shadow style, you could have a really nice design.
If it were me, I'd start again and work on just one face until I'd nailed it. Break it down, probably start with Sisko (the easiest of your quartet) and get that technique and level of detail right.
My only specific suggestion about the compostion of your design is to use a later version of Picard. In the first season of Next Gen he looks a little too fresh faced and lean.
Don't rush this (no pun intended) and you'll have a really great design. Good luck. :)
Yes, better. The likeness is good and you chose a noble, thoughtful looking image of Sisko for reference. Well chosen source will help make this design. If you can capture the essence of each captain it will make what is a good idea into a great design.
I note you did far more of the head than you had to, but it's all good practice. Don't be afraid of putting curves on those vector lines. :)