I think a little context is relevent. From everything I have read, it is the years on the contract (and thus bottom line total value), and not the per year value of the contract that scares Hendry. At Giles age of 35, I think Hendry is very comfortable paying Giles top dollar for a 2-3 year contract (total value 30 million or so). I think he is very uncomfortable adding a 4th year or beyond (total value high 30s or low 40s). I believe someone had posted the idea of a front-loaded contract for Giles, which, if Giles is open to it, is not a bad idea. If you're planning on paying him $10 million a year, and you're comfortable giving him only three years at this time, how about something like this: 2006: $11.5 million 2007: $10 million 2008: $8.5 million 2009: Team OR Mutual option for $9 million If Giles is interested in playing for a winner, you can sell the idea to him like this: The Cubs know how much they have to spend in 2006. They don't know how much they'll have available in 2008. This keeps them in a position to have a little extra money available then in case they need to add another piece to the puzzle to help maintain a winning team. The option for 2009 should be a team or mutual option. If Giles is still somewhat productive and the market on outfielders is thin after 2008, then the Cubs can pick up that option. It's less than the annual average of the contract, but more than the final year of the deal. It's also more than he made this season. If he wants more money, throw in some bonus incentives for 2007 and 2008. There's no need to front-load the cash in the contract. What the Cubs need to do is front-load the expensing of the contract. Professional sports must be the only business left in America that operates on cash accounting. If we are stuck with cash accounting, then pay Giles $8.5 in year one, but also put $3 in a bank account and charge $11.5 to the 2006 budget. Then in 2008, take the money out of the bank, add it to $8.5 from the 2008 budget, and pay him his $11.5 in 2008. As long as the whole contract is guaranteed, you can expense the money over the course of the contract any way you like. Adding in interest costs and time value of money complicates the calculations slightly, but that's how it works. In the real world you don't set up a bank account, it's just part of your capital budget, but nobody measures the profitability of their business on a cash basis. If the Cubs had expensed more of Maddux's contract in years 1 and 2 so that he only hit the budget this year for $5 million, nobody would be complaining about his contract.