5. Adam Loewen
The fourth overall pick of the 2002 draft, the left-handed pitcher wasn’t signed until almost a year later when the Orioles inked him to a major league contract — a risky proposition for a 19-year-old prospect — worth over $4 million just before the deadline to his rights expired.
Baseball American’s 13th overall prospect in the 2004 rankings, Loewen struggled with control problems in his first couple seasons before finally putting his mechanics together and starring for Canada in the inaugural World Baseball Classic and earning his first call-up in 2006. However, a stress fracture in his elbow in 2007 would ultimately lead to his undoing as a pitcher after his elbow again failed him in 2008.
Loewen declared his pitching career over and was determined to make it back to the majors as a hitter, but he bolted for a minor-league deal with Toronto where he’d return to the majors as an outfielder in 2011. Injuries certainly played a role in Loewen never living up to the hype created with a lengthy holdout upon being drafted, but the Orioles’ hopes of him becoming their future ace never remotely came close to materializing as he finished his pitching career with a 5.38 ERA.
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