Its all risk vs. reward. The longer you wait to sign the bigger the risk you are taking on as a player. Likewise, the earlier you sign a player, the bigger the risk you are taking on as an organization. Braun didn't leave money on the table. He signed a market deal at a time where he felt comfortable with his risk tolerance, and the club did the same. Looking at this stuff 4 years down the road is moot. I KNOW Braun is smart enough to understand when and why he signed the contract, and will remember that reason. The what if game is really fun though. What IF Braun would have been injured the past two years, and only played in 60 games total. WOW, says all the fans and media, he sure ripped the Brewers on that deal.