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Schilling was drafted by the Red Sox in the second round of the 1986 draft.<ref name="bio">http://www.thebaseballcube.com/players/S/curt-schilling.shtml</ref> On the field, he was known for his tremendous pro potential. He was also known as something of a rebel partly due to his wild hair styles. Said then Red Sox GM Lou Gorman, "He wasn't what I'd call a maverick but he was a little different."<ref name="stark">Stark, Jayson. "How the Red Sox lost on Schilling"; ''Philadelphia Inquirer''; July, 1999</ref> In his first professional season with Elmira of the New York/Penn League, Schilling won seven of his fifteen starts with an [[ERA]] of 2.59.<ref name="bio"/> Schilling spent the 1987 season with Greensboro of the South Atlantic League. He lead the league in both losses(14) as well as strikeouts(169).<ref>http://www.thebaseballcube.com/leagues/1987/SAL.shtml</ref> The following year, he was bumped up to Boston's double A team in New BritianBritain.<ref name="bio"/> That season, the Red Sox were making a major push for the playoffs and looked to acquire a veteran starting pitcher. They settled on [[Baltimore Orioles|Baltimore's]] [[Mike Boddicker]]. Boston agreed to surrender outfield prospect [[Brady Anderson]] due to their strong depth at the position. The Orioles asked for a second player in the deal, Schilling. Recalled Gorman, "Curt was the guy they asked for. They asked for him specifically."<ref name="stark"/> After the way the Red Sox lost the 1986 World Series, Gorman was willing to take the risk of trading away the two players. Schilling was surprised by the trade. Schilling: "We (players) were talking about the pitchers they might trade, and my name never was brought up."<ref name="stark"/> He made seven starts with Baltimore's double A team in Charlotte before getting the call to join the big league team. He made his major league debut on September 7, ironically against the Red Sox. Schilling pitched a strong seven innings and giving up three runs but got a non-decision in a game the Orioles ended up winning.<ref>http://www.retrosheet.org/boxesetc/1988/B09070BAL1988.htm</ref> He went on to make three more starts with the Orioles that year.