With the Orioles poised to make what might be the most important pick in team history, we decided to revisit some of the tougher selections in Orioles history and what they missed out on. Reminder: We recognize that the Orioles have made a number of very good first-round picks throughout the years, and we know we could perform this exercise with almost any MLB team. We’re just having fun. Or perhaps it’s more appropriate to say we’re having “fun.”

Given that the MLB First-Year Player Draft is even more of a crapshoot than the NFL’s version, we only considered actual first-round picks, not compensatory or competitive-balance selections. This all dates back to the last time the Orioles had the first overall selection (1989).

Here are “The 15 Orioles Draft Do-Overs.”

1991: Pick 9
Pick: OF Mark Smith
Could Have Been: OF Manny Ramirez (Pick 13)

This one stings. Smith reached the major leagues but played just 67 total games during three years with the Orioles and 414 games throughout an eight-year career. Ramirez was … pretty decent. At least when he wanted to be.

1993: Pick 19
Pick: P Jay Powell
Could Have Been: OF Torii Hunter (Pick 20)

While Powell never played a game for the Orioles, he had a decent enough 11-year career in the bigs, including playing a role for the 1997 Florida Marlins team that won the World Series. But just one pick later went Hunter, a future five-time All-Star and nine-time Gold Glove winner (who ironically made his MLB debut in Baltimore).

1995: Pick 21
Pick: P Alvie Shepherd
Could Have Been: OF Carlos Beltran (Pick 49)

While Shepherd never made the majors, his story is fascinating. He battled depression but saw his fortunes take a turn for the better following a 2013 brain aneurysm. He’s now in great shape and coaching high school football. It took awhile for another good player to be selected in ’95, but Beltran, a nine-time All-Star who slugged 435 home runs, would have been a good choice.

1997: Pick 26
Pick: OF Darnell McDonald
Could Have Been: This draft was a blood bath. So we’ll go with P Tim Hudson (Pick 185)

This was a strange draft because the Orioles actually made a very good selection just four picks earlier in then-catcher Jayson Werth, whom the team gave up on in 2002 to acquire pitcher John Bale. Eek. McDonald played just 17 games as an Oriole and 331 during his entire MLB career. But it was a long time before another good pick was made in ’97.

1998: Pick 26
Pick: OF Rick Elder
Could Have Been: OF Adam Dunn (Pick 50)

Not only did Elder never make the majors, he never reached anything above High-A. He finished with 462 fewer home runs than Dunn.

1999: Picks 13, 18, 21 and 23
Picks: P Mike Paradis, P Richard Stahl, OF Larry Bigbie and OF Keith Reed
Could Have Been: Again, not a ton. Maybe OF Alex Rios (Pick 19) or 1B Justin Morneau (Pick 89)

Obviously, most of the first round was historically bad for the O’s in ’99. Neither of the pitchers the Orioles drafted ever made the bigs, and Reed made six total MLB plate appearances. But they actually made up for it by taking Brian Roberts with their final first-round pick (50th overall, a supplemental selection). Few teams did much better after lefty Barry Zito (ninth overall) went to the Oakland Athletics.

2000: Pick 14
Pick: P Beau Hale
Could Have Been: 2B Chase Utley (Pick 15)

This is one of the ultimate “what-ifs” in Orioles history. Hale bounced around the minors for seven years, never making it above Double-A. Selected just one pick later, Utley could end up reaching the Hall of Fame once he’s eligible (2024).

2001: Pick 7 And 19
Picks: P Chris Smith and 2B Mike Fontenot
Could Have Been: 3B David Wright (Pick 38)

Smith was gone from the Orioles’ system by 2005, having never even made it to High-A. Fontenot became a decent player for a couple of years with the Chicago Cubs. Wright, the future seven-time All-Star third baseman, would have been really nice late in Round 1 with Cal Ripken Jr. set to retire.

2002: Pick 4
Pick: P Adam Loewen
Could Have Been: P Zack Greinke (Pick 6)

Loewen’s career story is absolutely fascinating; he made it to the big leagues as a pitcher with the Orioles and as a hitter with the Toronto Blue Jays, then transitioned back to pitching. But his career never involved him being a productive major leaguer. In 35 appearances as an Oriole, he pitched to a 5.38 ERA. Greinke, taken just two picks later, pitched to a sub-4.00 ERA in 11 of his first 15 seasons.

2004: Pick 8
Pick: P Wade Townsend
Could Have Been: P Jered Weaver (Pick 12)

Somehow Townsend is actually the Orioles’ worst pick on this list, as they were unable to even sign him out of Rice. But they didn’t miss out on anything; after being drafted again by the then-Tampa Bay Devil Rays the next year, he never made it above a brief stint at Double-A. Weaver was exceptional for the Los Angeles Angels from 2006-2014.

2005: Pick 13
Pick: C Brandon Snyder
Could Have Been: OF Jacoby Ellsbury (Pick 23)

Snyder neither stuck at catcher nor became a productive major-league first baseman. He finished with 37 plate appearances for the Orioles before the team unceremoniously parted ways with him in 2011. He was even briefly teammates with Ellsbury on the 2013 Boston Red Sox. Which is about the only reasonable comparison between the two.

2006: Pick 9
Pick: 3B Billy Rowell
Could Have Been: P Tim Lincecum (Pick 10) or P Max Scherzer (Pick 11)

You read that right. Instead of getting one of the best big-game pitchers in baseball history or … just one of the best pitchers in baseball history (both of whom were taken with the next two picks), the Orioles got Billy Rowell. The Lincecum-Scherzer duo has three World Series titles and five Cy Young Awards to their combined names, and Scherzer isn’t done yet. Rowell once hit .275 at High-A. So that’s nice.

2008: Pick 4
Pick: P Brian Matusz
Could Have Been: C Buster Posey (Pick 5)

Matusz was a can’t-miss prospect who will always be able to say he allowed just four hits and one walk in 30 career matchups against David Ortiz, whom he struck out 13 times. Sadly, he had to face non-David Ortiz hitters sometimes too. Just one pick later … a three-time World Series champion and four-time Silver Slugger Award winner and 2012 National League MVP. But to my knowledge, Posey never struck out Ortiz. So advantage Matusz there.

2009: Pick 5
Pick: P Matt Hobgood
Could Have Been: OF Mike Trout (Pick 25)

Hobgood is a really good guy who never made it above the Double-A level in part due to injury. And to be fair, a ton of teams missed on the New Jersey high schooler who … might end up going down as the best player in baseball history. But again, Hobgood is a really good guy.

2013: Pick 22
Pick: P Hunter Harvey
Could Have Been: OF Aaron Judge (Pick 32)

Hopefully Harvey will still end up panning out for the Orioles. It’s been a rough start due to injuries, but there’s still some promise there. It’s tougher to fathom he’ll end up being anything like Judge, however.

Issue 254: May 2019

Glenn Clark

See all posts by Glenn Clark. Follow Glenn Clark on Twitter at @glennclarkradio