Okay, sorry to do this … but, here’s one more post highlighting the failures of the O’s. We were an awesome team in 1996 and 1997, but then over a decade of mediocrity driven by terrible management decisions. The good news is, recently, the momentum seems to have swung in the right direction with some good teams. Things are looking up.

Now, for the bad news. Here are three Major League drafts where the Orioles really screwed up their first-round picks. We didn’t include anything in the last seven years because there’s still a chance for those drafts to pan out, though unlikely. Also, it’s painful that we drafted Brian Matusz ahead of Buster Posey.

1. 1987 Chris Myers instead of Craig Biggio

Craig Biggio

This was the draft where Ken Griffey Jr. was picked first overall. Chris Myers was a highly touted lefty out of Plant High School in Tampa. He played five years in the minors for the O’s, making it up to AAA Rochester and then played his final year with the Expos organization in 1992. He never made the majors, and after three years off, he played his last professional baseball game in 1995 with the Adirondack Lumberjacks of the independent Northeast League.

What a crappy pick that never panned out. Unfortunately for Baltimore, quite a few quality big leaguers were drafted after Chris in the first round, including Kevin Appier (#9), former Oriole Delino DeShields (#12), Craig Biggio (#22), and Travis Fryman (#30). I’ll add an asterisk to that last one, because the Orioles did have another first round pick with Pete Harnisch with the twenty-seventh pick. Nevertheless, Myers was picked over everyone I just mentioned.

Some other solid players were picked up in that draft, including two pitchers from the 1997 rotation. Check out this list of people we passed over for Myers: Todd Hundley (#39), former Oriole Albert Belle (#47), Derek Bell (#49), Pete Schourek (#56), Jaime Navarro (#71), Ray Lankford (#72), former Oriole Mike Timlin (#127), Reggie Sanders (#180), former Oriole Marty Cordova (#198 – didn’t sign), former Oriole Mike Mussina (#273 – unsigned), Phil Plantier (#292), Mike Stanton (#324), former Oriole Steve Finley (#325), Troy O’Leary (#331), former Oriole David Segui (#455), Scott Brosius (#511), Jeromy Burnitz (#617 – didn’t sign), Bret Boone (#711 – didn’t sign), Darryl Kile (#782), Rob Nen (#831), former Oriole Scott Erickson (#884 – didn’t sign), former Oriole Jeff Conine (#1,226), and former Oriole Bret Barberie (#1,247 – didn’t sign).

2. 1992 Jeffrey Hammonds instead of Derek Jeter

Derek Jeter

1992 was a strong draft class with Phil Nevin coming in at first overall.

Hindsight is always 20/20. Hammonds was supposed to be a great player. He turned out to be a talented player who had a couple solid years (one in Baltimore), who couldn’t stay healthy. It’s a shame too, because he was highly touted coming out of Stanford. I remember going to Fenway Park in 1992, watching the U.S. Olympic team play an exhibition against South Korea. I was standing next to the dugout wearing an Orioles shirt, waiting for Phil Nevin and Hammonds to come sign some autographs. Hammonds looked at me with my shirt and said “nice shirt kid.” I liked the guy. He just never lived up to expectations.

In the first round, the O’s passed over Derek Jeter (#6), Preston Wilson (#9), Michael Tucker (#10), Shannon Stewart (#19), former Oriole Rick Helling (#22), Jason Kendall (#23), former Oriole Charles Johnson (#28), Jeff Schmidt (#29), and Johnny Damon (#35).

The later rounds featured some excellent big leaguers who did not play their home games at Camden Yards: Todd Helton (#55), Jason Giambi (#58), Jose Vidro (#155), Darin Erstad (#357 – didn’t sign), Jose Cruz Jr. (#436 – didn’t sign), Matt Morris (#724), Jermaine Dye (#1,210 – didn’t sign), and Mike Lowell (#1,352 – didn’t sign).

Okay, I get it … why the hell would you draft a shortstop when you have Cal Ripken Jr.? But, if we did, the Jeffrey Maier incident doesn’t happen in ’96, the O’s go on and win the ALCS and defeat the choking Braves in the World Series?

3. 2001 Adam Loewen instead of Prince Fielder

Prince Fielder

This was the draft where Bryan Bullington was picked first overall and B.J. Upton second.

Oh man, this one hurts. Canadian-born Loewen was selected fourth overall and won a grand total of eight games for the O’s, with his finest season being 2006 when he went 6-6 over 112+ innings, and a 5.37 ERA. You may be familiar with a guy named Prince Fielder (#7), who hits bombs. The Orioles did not pick him.

The best part is that Fielder is only one of a handful of first-rounders who the Orioles overlooked. How about Zack Greinke (#6), Jeremy Hermida (#11), Nick Swisher (#16), Cole Hamels (#17), James Loney (#19), Denard Span (#20), former Oriole Jeremy Guthrie (#22), Joe Blanton (#24), and Matt Cain (#25).

Imagine if one of these guys played for the O’s: Joey Votto (#44), Jon Lester (#57), Brian McCann (#64), Jacoby Ellsbury (#674 – didn’t sign), Hunter Pence (#1,189 – didn’t sign), or Jonathan Papelbon (1,191 – didn’t sign).