If I had to do that, I would first find a picture of th e person, from the bust up. Then I would make it a grayscale (so I can print it in one color), the I would look for somekind of banner clip art, something like this picture.
I would place it under the bust and would write the name in there, or his title/position in the team. Maybe decorate it a little bit more and Voila!
Make it simple, use fancy font for the name, use a pic, people like pics in memorial shirts, we do that a lot in PR when somebody dies.
(That is what first came into my mind when I read your post)
In my webpage (titerewear) there is a shirt of a man, it is the last one in the homepage, it is called Adopte un Chef and has a smiling person, check it out if you want so you get an idea of what I say about a one color silkscreening picture shirt.
I am assuming you are going to screenprint. If you are going transfer you could go full color, thats up tp you.
I have another Idea you could use if going to screenprint. You could get a pic of the person and make some sort of lyrical abstraction of his face and make something different. You know, an abstraction but without losing the details that describe him. Check this image so you have an idea of what I mean.
Thats me in my cafepress store logo. You see, you could abstract his image and "make him a logo". This idea can also be used for vinyl (with plotter), as it has no great details.
There are many ways to work this out, if you need more assistance, Ill be glad to help, just post here or send a private message.
Good Luck!
Shirt in memory of a loved one 
