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Boston Red Sox - Stephen Drew

The last time the Red Sox paid a guy named Drew a healthy amount to come in as a free agent, it didn't exactly go as planned. J.D.'s younger brother Stephen comes at far less of a financial risk (one-year, $9.5 million), but there are still questions whether his production (.223, 7 HRs, 28 RBIs in 79 total games with Arizona and Oakland last year) matches that price tag. He's also dealing with a concussion that has sidelined him since early this month.J. Meric, Getty Images