Re: Here's to a long career, cadet!
At the risk of sounding like a HUGE nerd, the red shirt thing only works with the original series... You have a Next Generation uniform there, so the joke is kind of lost. Captain Picard wore a red uniform, and he didn't die. ;)
I'm trying hard not to mention that the date in the background is almost 100 years after Starfleet would even issue TNG style uniforms, but then I'd REALLY start coming off as a basement dwelling freak.
All that being said, it's a funny and well drawn shirt, but it would be way better if it had a original series red shirt!