Pitchers are in a tougher spot than position players --- it's a little tough to "overuse" a left fielder. Injuries are a factor at either level, but the overuse (see TR's "Ouch" thread) and (argueably) less extensive training/medical facilities at college would lead me to believe a quality pitcher drafted high enough to know he was getting a serious look (and enough of a bonus to know the club had made an investment in him) should probably go with the draft.
As for stories, let's see, there's the old LL hero, touted for the first couple of rounds but with parents who laid down the law on college. He was signed to a major-perennial-CWS program, and hasn't pitched much since his sophomore year because of arm problems.
Conversely, there's the Grienke story and how strange is that?!
Maturity is the key either way: would he be able to handle minor league life, able to recognize how the organization regards him and hang in there or cut his losses as the case may be, would he go on to college a few years down the road if things didn't work out?
Or, can he handle the rigors of academics and athletics, and recognize when he needs to protect his body without getting too precious about it? If academics have always been a strong suit, that argues in favor of college.
Then there's a compromise route: consider a JuCo in a competitive conference like the Panhandle Conference here in FL. He can get his AA, transfer to a DI, and be constantly eligible for the draft.