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As mentioned, the Astros have nine retired numbers thus far. The first two came under tragic circumstances. Jim Umbricht’s 32 was retired in 1965 following his death to melanoma at the age of 33. He only played the final two seasons of his five year career (1959-1963) with the then-Colt .45s, and put up a total of four bWAR with them (due to the nature of the stat, he only had about three bWAR for his whole career—his time with the Pirates was a negative). Despite this, he has left a huge impact on the team; according to Wikipedia, the team MVP award is also named after Umbricht.
Pitcher Don Wilson had his number (40) retired a decade later, after his death by carbon monoxide poisoning. Unlike Umbricht, Wilson had an already extensive body of work with the team upon his passing. His nine year career (from 1966 to 1974, all years with the Astros) saw the promising 29-year-old throw two no-hitters and stake an early claim to the title of the franchise’s best pitcher. His 30.2 bWAR with the team still ranks third among pitchers to this day.
Subsequent honoring has come under happier circumstances. Mike Scott and Jose Cruz saw their numbers, 33 and 25, respectively, retired together in 1992. Scott threw with the Astros from 1983 until 1991, and put up 23 bWAR with them (not to mention his NL West-clinching no-hitter in 1986). His four years with the Mets (prior to his time with the Astros) add little to his total career value.
Jose Cruz was the first hitter honored by the team. He arrived with the Astros in 1975 after five undistinguished years in St. Louis, and stayed in Houston until 1987 (1988 would be his final season, which saw him struggle in New York pinstripes ). His time in Houston accounted for 49 of his 52 career bWAR and 51 of his 55 career fWAR (marks which are fourth and fifth in team history, respectively).
Nolan Ryan, No. 34, was next to be honored. Ryan, who pitched from from 1968 to 1993 (and two games in 1966), spent 1980 through 1988 in Houston. The Houston native put up 26 of his 85 career bWAR with his hometown team.
Larry Dierker was the first player to get his number retired after the team moved into their new stadium (although he also spent time as the team’s broadcaster and manager, where he won a Manager of the Year Award and four NL Central titles). No. 49’s career was essentially spent entirely with the Astros; his last season, 1977, saw him pitch just under 40 innings for the Cardinals. Dierker was the longtime franchise leader in bWAR among pitchers, with 38.1. He pitched for the team between 1964 and 1976.
The chronically-underrated Jimmy Wynn was honored next. Wynn led the team in both bWAR and fWAR when he retired, although he has since been passed five times in both categories. Wynn played with the Astros from his start in 1963 until 1973, a time which saw number 24 put up 44 bWAR and 45 fWAR. He would play four more seasons after leaving the team, totaling 60 career bWAR and 61 career fWAR, both borderline-Hall of Fame numbers.
The two most recent honorees are ranked 1-2 in both systems. Both websites have No. 5, Jeff Bagwell, first. Bagwell spent the entirety of his career, which lasted from 1991 to 2005, with the Astros. Both bWAR (80) and fWAR (84) have him as a Hall of Fame lock-type player. His longtime teammate Craig Biggio, also a career Astros and Hall favorite, places second on both lists. No. 7 amassed 66 bWAR and 71 fWAR in his career, which went from 1988 to 2007.