I don't have any data to back this up but my guess is about 10% of these types of FA deals favor the team and the other 90% favor the players. Free agent deals rarely end up being worth it when you go to 5 years. Looking at the 2014 offseason here are all the contracts signed for at least 3 years & decent money, with how they turned out (so far in Max & Lester's cases)... Max Scherzer | 7/210 | 32.5 fWAR, 34.7 rWAR | TEAM Jon Lester | 6/155 | 16.8 fWAR, 17.9 rWAR | FAIR Pablo Sandoval | 5/95 | -1.1 fWAR, -0.1 bWAR | PLAYER Hanley Ramirez | 4/88 | 1.3 fWAR, 1.4 rWAR | PLAYER Russell Martin | 5/82 | 12.5 fWAR, 8.4 bWAR | FAIR James Shields | 4/75 | 0.8 fWAR, 2.7 rWAR | PLAYER Victor Martinez 4/68 | -3.7 fWAR, -1.8 bWAR | PLAYER Yasmany Tomas | 6/68 | -0.6 fWAR, -2.5 bWAR | PLAYER Nelson Cruz | 4/57 | 15.7 fWAR, 17.0 bWAR | TEAM Ervin Santana | 4/55 | 7.2 fWAR, 10.8 rWAR | FAIR Chase Headley | 4/52 | 5.9 fWAR, 4.9 bWAR | PLAYER Brandon McCarthy | 4/48 | 2.7 fWAR, 1.9 rWAR | PLAYER David Robertson | 4/46 | 6.0 fWAR, 5.8 rWAR | FAIR Nick Markakis | 4/44 | 5.8 fWAR, 6.6 bWAR | FAIR Melky Cabrera | 3/42 | 2.2 fWAR, 3.7 bWAR | PLAYER Francisco Liriano | 3/39 | 4.6 fWAR, 2.7 rWAR | PLAYER Andrew Miller | 4/36 | 7.2 fWAR, 8.8 rWAR | TEAM Billy Butler | 3/30 | -1.1 fWAR, -0.6 bWAR | PLAYER By my count that's 18 deals with the team "winning" three, five more that were fair then the last ten being overpays of varying degrees. In total it looks like $1,290,000 (yes, that is one billion two hundred ninety million dollars) were spent on those 18 players, who have produced in the neighborhood of 105-132 WAR, with three years total left to go between Max & Lester. Assuming another 10 WAR for those last three Max & Lester seasons & you're looking at somewhere between 9.1 & 11.2 million per win. You could almost say when it comes to free agency, it often pays to not spend. That's good research. My only quibbles with the no free agent strategy is that teams have to fill out their rosters, and sometimes the only players available are those on the free agent market. And by signing free agents (instead of trades), nothing is lost from the organization except for money. And all WAR isn't valued equally. Getting enough wins to reach the postseason is more valuable that other wins.