Here's a look at long term free agent contracts for players who actually reached FA from 2007-12. 39 players signed contracts for 4 or more years. Here's the average cost per WAR that these players have produced (keep in mind that Fangraphs pegs 1.0 WAR as worth $7 million): 6 players - Negative WAR - can't even calculate their value! 12 players - $10M+ per WAR 4 players - $8.0-9.9M per WAR 7 players - $6.0-7.9M per WAR 7 players - $4.0-5.9M per WAR 3 players - $3.9M or lower per WAR - The average yearly WAR for each of these players was 1.9 - The average yearly salary for each player was $14.9M - 11 players have averaged 3.0 WAR a year or better (Adrian Beltre is the best FA - 22.7 WAR in four years - 5.7 average) In the end, teams are paying roughly $15M a year for these guys to produce 1.9 WAR annually. It's not a terrible return, but it's not great either. As you would expect, a lot of the value is often produced early in the contracts, with diminishing returns as the player ages. Please note that 13 of these contracts still are in process. While there's a chance some players improve, the odds are that they will only get worse (example, A-Rod has averaged 3.4 WAR over the length of his deal. It's unlikely that improves over the next three years). Doesn't mean they can't get better (Prince, for instance, missed most of last year, so he could easily improve), but for most of them, a decline is more likely. Obviously, I didn't factor in years and money that haven't occurred. So if a player was four years into a 5-year contract for $50 million, I calculated it at 4-years and $40M. I used Fangraphs for WAR. Also, I only used players who actually hit free agency (this list is easy to find). Finding the contracts of all the players extended by their teams prior to FA is difficult. Final note, any voiding contracts, like Sabathia's, I just ignored. Figuring out how to calculate that was just not in the cards.