This week the Boston Globe contained an article about the second career of famed Red Sox pitcher, Curt Schilling.  Those who didn’t watch every game of the 2006-2008 baseball seasons and missed Schilling’s non-stop plugs will be surprised to know that Schilling owns a video-game production business that is, not totally shockingly, potentially going to be a massive disaster.  He started the business in the off-season following the 2006 season and cited his hard work on the endeavor as the central cause for his “100 pounds overweight arrival” at ’07 spring training, which was about as welcome a development to Sox Brass as the fact that he called his company “Green Monster Games”.

The story of the professional jock turned entrepreneur is not a new phenomenon.   In fact, 15 minutes of internet surfing will provide enough stories of profligacy and stupidity to plaster the interior of a half-built 80,000 square foot indoor soccer and rock climbing facility in suburban Boston, which incidentally, is exactly the prop used by former Boston Celtic Dana Barros in his "make most of my money dissappear" trick a few years back.  www.boston.com/sports/basketball/celtics/articles/2006/05/30/barros_attempts_to_rebound_from_failed_business_venture/

In the recent past Ron Artest decided that his one in a million physical gifts that allowed him to make 50 million dollars in 4 years while doing things such as punching his boss in the face, slapping his wife, and being arrested for starving his Great Dane to death were simply not enough and decided that his skills would transfer nicely into the world of music, specifically into the production of some of his own songs that he marketed from his car window on the way out of the players lot during the NBA playoffs and which he informed members of the media were "more of a priority" than his pesky basketball career. http://www.bvonsports.com/2009/11/23/ron-artest-music-/

By now most people have heard the story of the rise and fall of Lenny Dykstra who managed to retire from a successful career as a steroid user and baseball player with the Phillies with almost no money, then managed to make about 50 million by opening a chain of car washes, then somehow did enough investing or paid enough money to get CNBC’s Shameless Jim Cramer  to say that he was “one of the best stock pickers around” which lead to some network entering pre-production on a television series about the Lenny Dykstra Empire, which had to be cancelled before it aired because he managed to go broke in about 18 months by  employing said stock picking strategy and also putting most of his wealth into publishing a magazine targeted at professional athletes with articles about issues of wealth management which surprisingly didn't do very well.  Ultimately, he found out he was totally bankrupt when a news camera showed up at his house where he had no furniture or belongings  except a photograph of a German Sheppard which he claimed he was going to buy  for $10,000. http://deadspin.com/5302008/lenny-dykstra-lets-the-world-know-hes-flying-higher?autoplay=true

Bronson Arroyo also tried to walk and chew gum when he was a thoroughly underwhelming pitcher for the Red Sox.   He took a short-money arbitration buyout from the team and attempted to close his earning gap by capitalizing on his overrated looks and terrible guitar playing and singing to cut a record full of “almost exactly like the album cut only crappier” cover tunes which turned out to be a harder way to get rich than getting traded to the pathetic NL Central where a 165 pound frame and a 12-win season get you $25 million guaranteed.   http://video.google.com/videoplay?docid=6732328266441465611#

Mike Tyson and Cecil Fielder shared a level of irresponsibility that make them hard to touch on the All-Century Cash Hemorrhage Team, but the all-time best athlete-turned –anything-other-than-sportscaster is Oscar De La Hoya, who for a brief period of time, decided that he wanted to be a leather-pants-wearing Latino crooner in the style of Enrique Iglesias only without the looks, or any ability to carry a tune, or even hit a note.  Through pure serendipity I happened to catch his performance of “Run to me” live on Tonight with Jay Leno in 2000.  This performance remains one of the funniest things I’ve seen in my life and thanks to the splendor of the internet, the music video it spawned can now be one of the funniest things you have seen.  http://www.youtube.com/watch?v=d89IFcJD07A  Despite a level of creative/artistic badness that is virtually unrivalled, Oscar’s foray caused only minimal damage because he had enough sense to listen to his image counselors who told him that he should stick to throwing punches.

I get the sense that Curt won’t be so lucky.  I get this sense because Curt has never let common sense or the opinions of others assist him in not doing or saying things that are stupid.  I also get this sense because the Globe piece quotes Schilling as saying he has invested “most” of the money he ever made in this business such that his family will live or die, with the success or failure of the company he now (for some reason, probably the reason that the Red Sox sued him for a bazillion dollars) calls 38Pitches Studios.   All we can do now is wait, and be thankful this attempt at relevance doesn’t involve leather pants.