Guys, Fred Smith didn't go to Vegas to try winning the $27,000 gambling. Instead he went to Vegas hoping to see Howard Hughes and get an investment in FedEx (then Federal Express), and he won the $27,000 while waiting to see Hughes. Hughes didn't invest, but General Dynamics did, as I recall, $5 million. Check the story with Fred, Roger Frock, Art Bass, Charlie Brandon, Norm Waite, Leon Tyree, Mike Basch, and others.
Page 134 of "Changing How the World Does Business" (search on google books):
"by mid-July our funds were so meager that on Friday we were down to about $5,000 in the checking account, while we needed $24,000 for the jet fuel payment."
...
"you mean you took our last $5,000 -- how could you do that?"
Original headline was factually correct (even though, as you correctly point out, the $5,000 part wasn't mentioned in the article)
I can't back it up with another source, but I have heard this / read this assertion somewhere. It's at least founder-culture folklore. Trying to remember which book I read it in... will edit if I can find / remember.