If he sticks in the majors at this point, I believe he'll be arbitration eligible after next season (as a super-2?), and wouldn't be a free agent until after 2012. That means it's going to a take a long time for him to approach the $10m salary range. In other words, there's big time incentive for him to sign something before then. I think the Cubs should stronly consider signing him to a deal after this year that takes up all his arbitration years, 2008-2012 that would pay him something like: 2008- $0.75m 2009- $2.00m 2010- $5.00m 2011- $7.00m 2012- $10.00m club option with $0.25m buyout That would guarantee him $15m, probably well under what he'd make if he kept pitching well and hit arbitration every year, but it would secure his financial future and put him on the road to racking up the dough. The Cubs haven't been a team that does deals like this (San Diego, Arizona and others have). But I think it's a good way to keep cost certainty on your best and most likely to succeed young players.