The Orioles have had their share of draft wins over the years, but not every early pick turns into a franchise piece. For every Manny Machado or Mike Mussina, there are names that barely register now, even if they once carried big expectations on draft day. And while it’s far too soon to stamp Jackson Holliday a bust - he’s still only 22 - Baltimore’s history does include a few early selections that fit the label much more cleanly.
Chris Smith is one of the clearest examples. Baltimore took the left-hander from Cumberland University with the 7th overall pick in the 2001 MLB Draft, hoping he’d grow into a rotation arm.
Instead, Smith logged just 52.2 innings over 24 minor league games and never came close to becoming the kind of pitcher the Orioles envisioned. His career numbers tell the story: a 7.52 ERA, a 2.194 WHIP, and a 7.2 BB/9 rate.
With that kind of control, he never really got a foothold.
Matt Hobgood came with a different kind of buzz. The Orioles grabbed him 5th overall in the 2009 MLB Draft after his senior season at high school brought him the Gatorade National Player of the Year Award.
On paper, it looked like Baltimore had landed a high-upside arm. In practice, it never came together.
Hobgood finished with a 1.482 WHIP in the minors, made it only as far as Double-A Bowie in 2015, and then shoulder surgery ended his career. The sting gets worse when you look at the pick right after him: the Giants took Zack Wheeler at No.
- Baltimore also missed out on him by one spot.
Then there’s Heston Kjerstad, the 2nd overall pick in the 2020 MLB Draft. Unlike Smith and Hobgood, Kjerstad has shown real production - just not where the Orioles need it most.
Across 319 career games and five minor league seasons, he’s hit .289 with an .853 OPS, and his best pro season came in 2024, when he launched 16 home runs for Triple-A Norfolk. But that success hasn’t carried over to the majors, and injuries have been a major obstacle, including a lengthy battle with myocarditis.
At 27, he still has time, but the line between promising prospect and Quad-A player is getting thinner.
In Other News...
The Final Piece Of The Shane Baz Trade Is Now In
The Shane Baz trade finally has its last missing piece, and it comes from the Orioles side of the draft board. Tampa Bay used Baltimores 33rd overall pick on high school shortstop Taj Marchand, closing the loop on a deal that sent multiple prospects and that selection to the Rays in exchange for the right-hander.
For Baltimore, the trade has been a mixed bag on both ends. Baz has been uneven since arriving, with bouts of poor command, but he has usually worked deep enough to give the Orioles a chance to win. The prospects headed to Tampa Bay have followed different paths, from Caden Bodines rise into top-100 territory to Michael Forrets struggles after a Triple-A promotion, while Austin Overn has had a nice season and Slater De Brun has yet to debut. [Read more 🡒]
Orioles Look Smarter As Basallo Deal Ages Better By The Week
The market for young talent keeps moving, and the latest reminder came when St. Louis locked up rookie second baseman JJ Wetherholt on an eight-year deal that can climb well beyond the initial number. For Baltimore, it only sharpened the sense that the club may have been ahead of the curve when it reached its own long-term agreement with catcher Samuel Basallo, a player whose extension now looks more and more like one of the cleaner bets in the organizations recent run of early deals.
The timing matters here as much as the talent. Baltimore got Basallo done before he had built up much major league leverage, and before his negotiating position could really harden, which is part of why the agreement landed where it did. It also stood out in an organization where so many of the young names have been tied to Scott Boras, a group that usually does not rush into these kinds of commitments, making Basallos willingness to talk all the more notable as the Orioles continue to watch the rest of the market reset around them. [Read more 🡒]
Colton Cowser Shared The Awkward Draft Night Orioles Fans Never Knew
Colton Cowsers draft night story has a little more awkwardness to it than most Orioles fans ever heard about. The outfielder, now part of Baltimores core, recently revisited the 2021 MLB draft and how the night unfolded after a round of pre-draft workouts, conversations with several teams and a celebration planned with family and friends. By the time the Orioles were on the clock, Cowser was already deep into the nerve-racking part of the process that comes with waiting to hear your name called.
Cowser said the Orioles interest was real enough to keep him on edge, and the night only got more memorable from there as the news reached him in a roundabout way. He also talked through the range where he was expected to land and how quickly the draft can turn from suspenseful to surreal when a team makes a move that changes the script. For Baltimore, it is another reminder that the player who eventually became the fifth overall pick did not experience the moment in quite the clean, polished way fans might have imagined. [Read more 🡒]