The Colorado Rockies have built some of their best teams the old-fashioned way: by drafting and developing their own stars. Todd Helton, Troy Tulowitzki and Nolan Arenado all came through that pipeline, proof that the organization has been able to identify and grow real cornerstone talent.
But the draft cuts both ways. For every impact player, there’s a pick that never comes close to the billing. And when you look back at Rockies history, three names rise to the top for all the wrong reasons: Greg Reynolds, Riley Pint and Chris Freemen.
Reynolds is the one that still stings the most. A standout at Stanford, he looked like the kind of polished arm a team could build around, and Colorado believed it had landed its future ace when it took him at the top of the 2006 draft. Instead, the No. 2 pick never matched the hype.
His major league work with the Rockies was limited and rough. In 2008, Reynolds appeared in 14 games, went 2-8, and gave up 56 earned runs in 62 innings while striking out 22.
He also walked 26 batters, allowed 14 home runs and finished with an 8.13 ERA. Colorado tried again in 2011, but the results didn’t change much: 13 games, 32 innings, 22 earned runs and a 6.19 ERA.
For a player taken that high, it was a massive miss.
What makes that pick even harder to swallow is the list of players still on the board after Reynolds went. The source notes that several players who were available and selected shortly after him could have altered the direction of the franchise. Instead, the Rockies went with Reynolds, and the opportunity slipped away.
Pint’s story was different, but the disappointment landed in a similar place. Colorado took the hard-throwing right-hander with the same kind of ace-level hope, and the raw stuff was impossible to ignore. He was a high school pitcher who could hit triple digits and was viewed as one of the top arms in his class.
The problem was that the promise never turned into production. Control issues kept him buried in the minors, injuries piled on, and he stepped away from baseball more than once before finally reaching the majors.
By the time he made it to the Rockies, seven years had passed since he was drafted. His lone big league appearance was a rough one, and he didn’t even get through an inning.
Freemen’s case is a little less dramatic, but it still belongs in the same conversation. Taken as a supplemental first-round pick, he came into the organization with real expectations and moved through the farm system as one of Colorado’s better prospects. He eventually got three seasons with the big club, but the everyday player the Rockies were hoping for never arrived.
Over 151 games with Colorado, Freemen hit .225 with 64 hits, three home runs, 29 RBI and a .629 OPS. His time in the organization ended before his 28th birthday, and he was out of MLB after the 2007 season.
The Rockies have had their share of draft wins, and that matters. But these three picks stand out because of how much was expected and how little was delivered. Not every draft choice becomes a franchise piece, and these are three reminders of how quickly hope can fade when the projection never turns into the player.
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