Not sure that trade even makes the top 5 of "worst trades in franchise history"...but it was terrible nonetheless
Bobby Shantz for Carl Warwick and a scrub Mike Cuellar and 2 scrubs for Curt Blefary and a scrub. Rusty Staub for 3 scrubs Jim Wynn for Claude Osteen and a scrub. Bill Doran for Butch Henry and 2 scrubs. Lance Berkman for a RP and a bench player. Doug Rader for 2 scrubs Curt Schilling for a scrub John Mayberry for 2 scrubs Kenny Lofton and a scrub for Eddie Taubensee and a scrub Kenny Caminiti, Steve Fliney and scrubs for Derek Bell and more scrubs Obviously the Joe Morgan deal Who has more?
That scrub was relief pitcher Jason Grimsley, who has one of my all-time favorite baseball stories: when he was with Cleveland, Albert Belle got busted for using a corked bat, so the umps confiscate it and lock it in the umpire's locker room until after the game when they can send it to MLB and have it x-ray'd, dissected, whatever they do before handing down a suspension. Grimsley goes full Mission Impossible and climbs into the ceiling in the team clubhouse, across, and drops down in the ump room, replaces the bat with one they knew was legal, and exits via the same hole in the ceiling. The umps knew there were some shennanigans, because the bat was obviously not the same, and the #1 tell-tale was that it had a different player's signature on it. "We couldn't use one of Albert's because *all* of them were corked" he explained years later, once the story came out.
And he was heavily involved in PEDs as well. A federal investigation involving him was a huge part of the Mitchell report.
Some of those weren't really terrible deals. Obviously Schilling & Lofton ended up terrible and would be 1 & 2 for me. Morgan would be #3. The Derek Bell deal is probably #4. Berkman trade wasn't bad, because he wasn't good for the Yankees and was a pending FA. Wynn deal is hard to judge, but baseball criminally underrated him. The rest of those deals are just meh. Didn't lose much, but didn't gain anything. Where the snitch trade falls is the most complex. First and foremost, we won a World Series with Fiers providing valuable innings during the regular season. The big downsides were trading away Hader and of course the sign stealing scandal being discovered. It is entirely possible it would have eventually been found out. It is also very possible we would have won more World Series if we hadn't traded away Hader. Though I think we most likely end up dealing Hader for Giles and thus losing Hader still happens. Ignoring the sign scandal, I'd put it at #6, with it I would put at #5 above Wynn deal. The top 3 were franchise altering deals. We gave up 3 HOF caliber players for nothing, and they weren't pending FAs.
If you aren't old enough to remember the Astros being run by an Automobile Finance Company, you completely missed TOTAL DISASTER.
Jason Grimsley also is one of the most important but forgotten figures in baseball history. He was a drug used - and even more importantly, he was a huge figure in the PED era where he would procure it for other players, would introduce players to PED's and his contacts for PED's. He also was deeply involved in other cheating around the game. He decided which names he would disclose for PED use and which he would protect. He was big time.
