The two sides consummated the deal in April 2005. Crawford would earn $15.25 million from 2005 through 2008, the four years before what would have been his free agency date. The contract then called for an $8.25 million salary in 2009, Crawford’s would-be first post-free agency season, and another $10 million in 2010 (with a chance to earn up to $11.5 million based on various escalator clauses). If Crawford mad out his earnings, he would make $35 million over six years—one pre-arbitration season, three arbitration-eligible seasons, and two (would-be) free agency years. No one knew for sure how Crawford’s career would play out, and the D-Rays would be exposed if their promising young left fielder suffered a career-ending injury or an irreversible performance decline. Still, the potential was there for the Devil Rays to make a gigantic profit. Which is exactly what they did.

Baseball analysis website FanGraphs shows every player’s earned value on a year-by-year basis, based on a formula that measures a player’s batting and defense (or a pitcher’s pitching), then scales it against the going rate for free-agent talent in a given season. Through the first four years of the contract, Crawford’s performance added up to $55.7 million in value—nearly four times what he was paid in those seasons. In 2009, Crawford’s production netted 5.5 wins for Tampa Bay, worth $24.9 million on the open market—triple his salary for the year. By late June 2010, Crawford’s earned value had easily surpassed that season’s salary too. All told, Crawford produced $108.9 million worth of value for the Rays over the life of his contract, compared with the deal’s maximum value of $35 million.

Friedman’s next big coup came in January 2008, when the Rays signed starting pitcher James Shields to a long-term contract. Having already seen some of Crawford’s profit potential pay off, Friedman took an even more aggressive approach with Shields. After just 52 major league starts (including an impressive 12-8 record and a 3.85 ERA on an awful 2007 team), Shields had shown the Rays enough to earn his own multi-year offer. From 2008 through 2011, Shields would be paid $11.25 million, already a potentially huge bargain for a Rays team that believed it had found a top-tier starter.

But the kicker would come at the end of those four seasons, with the Rays tacking on not one, not two, but three club options. No team in baseball had so completely embraced the idea of club options or lobbied for that much latitude at the end of a deal. But Shields had one less year of service time under his belt than Crawford did at the time of his signing. As a pitcher, Shields was also a riskier investment. The higher attrition rate carried by pitchers compared with position players was a concern. Even more worrying was the 2002 shoulder surgery Shields had to remove a benign tumor; the procedure dropped the velocity on his fastball and left him wondering if he’d ever pitch again. But Shields had proved himself since then, developing one of the deadliest changeups in the game. If anything, those drawbacks gave the Rays more negotiating leverage. The deal to date has been a big success. Three years into the contract, Shields has been worth $44.4 million (market value) despite an erratic 2010 season. If he serves the contract’s entire seven-year term, including the club’s three option seasons, his maximum total salary would be $44 million. Less than halfway into the deal, the Rays have already made their money back.

Still, offering contracts to players who are two-plus years, or a year and change, into their major league careers? Big deal. At no point in a player’s professional career is his future so uncertain as when he’s toiling in the minor leagues. The vast majority of minor leaguers never even sniff the majors, and the tiniest percentage of them actually achieve some degree of success thereafter. For any player, even a "can’t-miss" prospect, getting the call to the show means a big celebration (and a sigh of relief). What if a team could convince a top prospect, on the cusp of making the majors, to trade in that uncertainty for an eight- or nine-year contract? What teenager or early-twenties up-and-comer, the idea went, wouldn’t want to lock up tens of millions of dollars before playing his first big league game?