Roush Fenway Racing and Red Sox owner John Henry decides he wants to sign the biggest free agent to hit the NASCAR market in years. After all this is the same guy who paid $103M this offseason for Japanese pitcher Daisuke Matsuzaka. He offers Dale Jr. a load of money to sign on with his Roush Fenway race team and join the likes of Matt Kenseth, Carl Edwards and Greg Biffle. Not bad. Henry doesn't stop there though. He now owns stakes in two of the most iconic sports brands in the world - Dale Earnhardt Jr. and the Boston Red Sox. Just imagine the cross promotional possibilities there