When Kyle Bradish takes the mound tonight in Boston, he'll make the first start of the next era of his career. However, after the recent announcement of Bradish's five-year, $90M extension, the Orioles' 29-year-old right-hander is squarely perched atop Baltimore's rotation for the foreseeable future. Since coming back from Tommy John surgery at the end of last season, Bradish has a 3.35 ERA across 139.1 innings with 153 strikeouts and a .229 batting average against. The timing of Bradish's new deal and the Average Annual Value may shed light on how the Orioles continue to approach their rotation moving forward. The Bradish deal offers hope that the front office will work out a deal with Rogers prior to him hitting free agency.