The Johan Santana trade (Feb. 2, 2008)

The trade: The Minnesota Twins dealt Santana to the New York Mets for OF Carlos Gomez, RHP Deolis Guerra, RHP Philip Humber and RHP Kevin Mulvey.

How it happened: Santana was arguably the best pitcher in baseball at the time, a 28-year-old power lefty who’d won two Cy Young awards and finished in the Top Five of the voting two other times. During his four full seasons in the Twins’ rotation, he led the AL in ERA twice and led in strikeouts and WHIP three times each. But the small-market Twins knew they wouldn’t be able to re-sign Santana when he was eligible for free agency after 2008, so they traded him away before the season began.

After a bidding war that involved the Red Sox and both New York teams, among others, the Twins found a match with the Mets. In exchange for Santana, they received four prospects, all of whom were 25 or younger. Gomez and Guerra were both ranked among the top 100 prospects in baseball by both Baseball America and Baseball Prospectus, and Humber and Mulvey were close to big league-ready arms.

The results: The return package could hardly have turned out worse for the Twins. All four prospects turned into duds, at least while they were in a Minnesota uniform. The three pitchers combined for only 15 appearances with the club, posting a 7.36 ERA. Humber had one moment of glory in the majors when he pitched a perfect game in 2012 — but he did so as a member of the Chicago White Sox, three years after the Twins jettisoned him.

The only prospect in the trade who saw major time with the Twins was Gomez, who became their starting center fielder at age 22 in 2008. But the free-swinging Gomez struggled in his two seasons in Minnesota, and the Twins dealt him to Milwaukee for a name that’s familiar to Orioles’ fans: shortstop J.J. Hardy. (Compounding the Twins’ problems, they then traded Hardy after one season to the Orioles for forgettable relievers Jim Hoey and Brett Jacobson, while Gomez emerged as an All-Star for the Brewers and Hardy an All-Star for the Orioles.)

Meanwhile, the Mets signed Santana to a six-year, $137.5 million extension during a negotiating window that completed the trade. They got their money’s worth in the first year of the deal when Santana went 16-7 with a league-leading 2.53 ERA, finishing third in the NL Cy Young vote. But Santana’s body broke down and he missed time with injuries every season after 2008. He pitched four seasons with the Mets, finishing with a 46-34 record and 3.18 ERA in 109 starts. In 2012, his final year, he threw the franchise’s first no-hitter.

As a postscript to the Santana tale, he joined the Orioles on a minor league deal in 2014 and was primed to return to the majors until he tore his Achilles tendon at extended spring training in June, ending his season — and, effectively, his career.

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