The length doesn't matter with these lifetime contracts. Free agent contracts now cost upwards of $7-8 million per WAR, possibly more now since at least 17 teams have a record payroll this year. The cost of the contract is simply the expected remaining lifetime value of Cabrera--the years and annual salary are mostly irrelevant. Right now, Cabrera is playing at a value of $50-60 million/year. That's what he deserves. But the Tigers obviously aren't going to pay him that much in a single season, so they extend the contract out over 10 years to cover the rest of his career--overpaying in future seasons to make up for underpaying in the next few seasons. My opinion is that he only needs to post 40 WAR to make the contract worthwhile from purely a production standpoint. That's about 5-6 seasons at his current pace. When you add in the value of marketing, merchandise, and his potential contribution to a championship, then the total figure makes sense. All that being said, I agree with everyone else that this is a stupid contract. Detroit isn't LA or NY. Plus, they already had him signed at a tremendous bargain for the next two seasons--likely to be his most productive of the next 10. There was no rush to sign the deal now, his value wasn't going to go up. It seems like these deals do not affect small market teams' ability to make the playoffs or remain generally competitive, but it really hurts them in the postseason. Lately we have been seeing small market teams with cores of young, pre-arbitration talent get beaten in the playoffs by big market teams with veteran superstars. I'm not sure if this trend will continue.