In 1998, the Colorado Rockies were in an odd place. They won 83 games for the second straight season but things weren’t necessarily looking up. Entering June 2 (the first day of the draft), the Rockies were 24-33. The main reason was the Rockies starting pitching staff that was awful. In March and April alone, they had a ghastly 7.30 ERA.
The Rockies also decided to trade each of their previous #1 draft picks and one of their two second-round draft picks in the previous two years to the Montreal Expos for reliever Dave Veres and second baseman Mike Lansing.
But the Colorado Rockies had a well-ranked farm system entering the 1998 MLB Draft.
Despite that, the Colorado Rockies still had five prospects in the top 100, per Baseball America. One got to the majors and did very well like Todd Helton, who was Baseball America’s #11 overall prospect, a few got to the majors for a few seasons and didn’t live up to the hype for one reason or another (e.g. Ben Petrick and Shawn Chacon), and a few never panned out at all (e.g. outfielder Derrick Gibson and pitcher Lariel González were in the top 100 and they combined to play 18 games in the majors).
So that’s part of the reason why the Rockies were comfortable trading away three of their top four picks in recent years and why they were comfortable with sacrificing their first-round pick to Houston after they signed Darryl Kile as a free agent.
However, they still had three first-round draft picks since they got two first-round picks for losing Andres Galarraga to the Braves in free agency and a first- and second-round pick for losing Walt Weiss in free agency (again, to the Braves).
But the Rockies struck out on all three picks.