Imagine if Joe Morgan had spent his prime seasons in Houston instead of Cincinnati.
Picture Kenny Lofton setting the table for Craig Biggio and Jeff Bagwell during the 1990s.
What if the Astros had re-signed Randy Johnson, which would have justified parting with three top tier prospects for what was nothing more than a two-month rental?
Let your imaginations run wild as we look back at five trades that left Astros fans shaking their heads and wondering what was on the minds of the general managers who pulled the trigger.
The Astros contributed mightily to the historic 1969 Mets-Orioles matchup (See No. 4 for how Houston helped the Mets).
Frustrated by Mike Cuellar's 8-11 record in 1968, the Astros dealt the talented southpaw to Baltimore along with minor leaguer Elijah Johnson and SS Enzo Hernandez for minor leaguer John Mason and OF Curt Blefary, the 1965 AL Rookie of the Year who had recorded three straight 20 homer seasons before hitting .200-15-39 in 1968.
Blefary improved his batting average to .253 in 1969, but hit just 12 homers in his only season as an Astro. Cuellar struck gold in Baltimore, winning AL Cy Young honors as he went 23-11 with a 2.38 ERA en route to helping the Orioles to the pennant.
It would prove to be the tip of the iceberg for Cuellar, who won 24 games in Baltimore's World Series title run in 1970. He eclipsed the 20-win mark twice more (1971, 1974) as he went 143-88 (3.18 ERA) in eight seasons with the Orioles.
The club's first true star, Jimmy Wynn, slammed 223 homers and stole 180 bases in 11 seasons with the Astros. But after hitting just .220 in 1973, Houston made "The Toy Cannon" expendable, moving the 31-year-old All-Star to Los Angeles in exchange for lefty hurler Claude Osteen and minor leaguer Dave Culpepper.
Osteen went 9-9 in 23 appearances with Houston before being traded to St. Louis in August of 1974. By then, Wynn—named to the All-Star team—was well on his way to a .271-32-108-18 campaign that keyed Los Angeles' run to the National League pennant.
Wynn made the All-Star team again in 1975 and played two more seasons before calling it a career. Osteen's career ended after finishing 7-16 with the White Sox in 1975.
Rusty Staub was emerging as one of the best hitters in the National League. In an era where offense was suppressed, Staub batted .333 in 1967 and .291 the following season. At just 24, the two-time All-Star was on his way to star status.
That didn't stop the Astros from dealing him to the expanding Montreal Expos for OF Jesus Alou and 1B Donn Clendennon. Clendennon refused to report to Houston and was dealt to New York, where he played a key role in the Mets' storied run to a World Series title.
Instead, the Astros received pitchers Jack Billingham and Skip Guinn, along with $100,000. Billingham had three uneven seasons with Houston, while Staub played an additional 18 seasons with the Expos, Mets, Tigers, and Rangers, becoming the only player in history to record at least 500 hits with four different teams.
The Astros sent shockwaves through the baseball world when they acquired Mariners ace Randy Johnson at the trade deadline. Despite the stiff price of prospect P's Freddy Garcia and John Halama and SS Carlos Guillen, "The Big Unit" made Houston the odd-on favorite in the National League
Johnson delivered, going 10-1 with a 1.90 ERA and 116 strikeouts in 84.1 innings as the Astros recorded a team-record 102 games and the NL Central crown. Johnson was stellar in the postseason (1.93 ERA), but was 0-2 as the Padres shocked the Astros in the NLDS.
Houston made a half-hearted attempt to keep Johnson, but the big lefty chose to sign with Arizona, where he went 118-62 with a 2.83 ERA over the next 10 seasons, adding four straight Cy Young awards (1999-02) and the 2001 World Series title.
As for the prospects, the Astros gave up for two months of Johnson? All three were key parts to Seattle's AL record-tying 116 wins in 2001, with Garcia going 18-5 as the Mariners' ace. Garcia enters 2010 with 121 career victories, while Guillen emerged as a three-time All-Star shortstop and won a World Series with Detroit in 2006.
A former All-Pac-10 guard at Arizona, Kenny Lofton chose the diamond instead of the hardwood. He made his debut with Houston late in the 1991 season, hitting just .203 in 74 at-bats.
The Astros chose Steve Finley as their long-term answer in center when they dealt Lofton (and INF Dave Rhode) to Cleveland for P Willie Blair and C Ed Taubensee, whose promising left-handed power made him the crown jewel of the trade.
Taubensee hit a paltry .234-1-14 in 203 games as an Astro before finding a level of success in Cincinnati. Blair went 5-7 in 29 appearances in Houston and was picked by Colorado in the 1992 expansion draft.
All Lofton did was become the most prolific leadoff man in the American League during the 1990s, leading the AL in steals five straight times (1992-96) and six All-Star nods en route to a career that saw him bat .299 with 622 steals.
There might have never been a "Big Red Machine" had the Astros not been in a rush to jettison the then-27-year-old Morgan, who was coming off a season in which he led the NL with 11 triples, hit 13 homers and stole 40 bases.
Morgan went to Cincy along with P Jack Billingham, OF's Ed Armbrister and Cesar Geronimo, and INF Denis Menke in exhange for 1B Lee May, 2B Tommy Helms, and OF-2B Jimmy Stewart. May was envisioned as the much-needed power source for the Astros, while the slick-fielding Helms would provide better defensive stability over Morgan.
Needless to say, the trade changed the course of baseball history. Morgan helped the Reds to five NL West titles, three NL pennants and two World Series crowns and was named NL MVP in 1975-76, securing a path to the Hall of Fame in the process. Billingham, Armbrister, and Geronimo each played roles in Cincinnati's grip of the NL as well.
Helms hit a quiet .269 in four seasons with Houston, and while May hit 81 homers in an Astros uniform, his all-or-nothing approach at the plate wore thin after three years, leading to the club trading him to Baltimore in December of 1974.