Miguel Cabrera is the player that Fielder's dollar figures should be patterned after if he takes arbitration season-by-season. I don't think Cabrera and Howard are that different as far as the process works...it tends to be based on past performance and comparable players in terms of recent performance, rather than on projections of future value. That's not to say that your point is invalid...going forward we can expect Howard to peak and decline long before Fielder does. It's just that the arby process itself doesn't seem to take that into account. A smart FA market would presumably consider the age of players, so Fielder could expect a premium over Howard's salaries in that respect...however the process (for better or worse) also rewards awards (say that three times fast), so Howard's ROY and MVP earned him some money that Fielder wouldn't necessarily get. This is where Boras makes his clients money...in a negotiation he'll insist that Fielder is not only comparable to Howard but better, despite the hardware, and extract a few more million dollars. He also knows that the market has escalated (10% or so) from year to year, so with a guy like Fielder you can probably maximize earnings by going year to year. I certainly agree Cabrera's deal is probably what either guy (Howard or Fielder) would be using as a comp for a potential long-term deal. Here's what cot's says: 08:$11.3M, 09:$15M, 10:$20M, 11:$20M, 12:$21M, 13:$21M, 14:$22M, 15:$22M He would be a FA after 09, so the six free agent years average $21M each, and the last two arby years ramp up to that. Eighteen to twenty million is sort of a benchmark number for a guy like this, but four years from now I don't think $20M will seem like a lot of money any more...assuming salaries continue to inflate as they did in the last few years. So with Prince, presumably you'd try to lock him up for 09, 10, 11 (three arby years), then at least one FA year (12), and then have an option for the final year. So, maybe $9M, $12.5M, $16M for the arby years, $21M for 2012, $22M for 2013? That's $80+M for five years...how does that look? Prince would still be hitting the market in his prime, with a hefty amount of money in the bank and the opportunity to hit the jackpot in free agency. Then again, Boras would probably want a premium, for forgoing the opportunity for free agency, so that might not even get it done...how about 5/$90M? I just don't know.