Note: This is a retrospective of moves made in the 08-09 offseason, and during the 2009 season. So you won't find "Signing Kaz Matsui" in the list of Moves That Worked, Moves That Didn't.
Moves That Worked
Trading Pudge for two prospects
Pudge was supposed to be the stop-gap at catcher for two reasons: (1) To allow time until Jason Castro was major-league ready, and (2) to keep Quintero from becoming the full-time starter. It worked alright, but it was clear that Pudge was old, and his effect on the pitching staff was negligible (Wandy originally attributed 09 success to working with Pudge, and then imploded in May/June, and then righted the ship - even after he was gone). So to trade Pudge to the Rangers for anything more than a copy of The Sandlot 3 and some Icy Hot was impressive. To get two prospects out of it is nothing short of amazing. The Rangers acquired him to help with their push for the post-season, but were 14-14 in games Pudge started down the stretch.
The two players the Astros received have done well. Matt Nevarez, a 22-year old RH reliever, only played in 8 games (8.1IP), but had a 0.00 ERA / 0.36 WHIP, four saves, and 13K:0BB. 22-year old infielder Jose Vallejo had limited time with the Astros, but put together a .289/.318/.349 line at Double-A Frisco, and was 7x20 (.350/.350/.500) in seven games at Round Rock.
Signing Chia-Jen Lo
The Astros' first foray into Pacific Rim scouting culminated in the November signing of RHP Chia-Jen Lo. The 23-year old split time between Lancaster and Corpus, where at Lancaster, C-Lo had a 1.78 ERA / 0.91 WHIP in 25.1IP, with a 36:13 K:BB ratio. At Corpus, despite battling injury, C-Lo had a 2.31 ERA / 1.28 WHIP, allowing just one homer in 39IP at Corpus. He'll compete for a bullpen spot in 2010, and will start at Round Rock if he doesn't get the spot out of Spring Training.
Claiming Chris Coste
It may not look like it, but the Coste experiment wasn't such a bad one. Despite posting a .204/.259/.252 line with the Astros, with five extra-base hits in 103 plate appearances, having Coste on the roster allowed Ed Wade the ability to trade Pudge. Making 14 starts behind the plate, and 13 starts at 1B to spell Erstad when Berkman went down, Coste didn't make a single error behind the plate, and only one at first.
Claiming Jeff Fulchino off waivers from the Royals
When the Astros claimed the huge righty off waivers from the Royals last December, he was coming off a season in which he allowed 14 ER in 14IP for Kansas City and a combined 4.87 ERA for Double-A NW Arkansas, and Triple-A Omaha. So I don't know that anyone was expecting Fulchino to throw up a 3.40 ERA / 1.18 WHIP over 82IP for the Astros this year, earning Rookie of the Year honors from the Houston BBWAA. He struck out 71 batters in 82 innings, and has put himself in a position to emerge as an 8th inning option in 2010.
Letting Ty Wigginton walk
The Astros were looking at a hefty little bump from Wigginton's $4.35 million salary in 2008. Instead, Easy Eddie declined to offer him arbitration, and he signed with the Orioles, where he signed a two-year $6 million deal. Wigginton hit .273/.314/.400 with 11HR and 41RBI, but also played below-average defense at 1st and 3rd. The offense was okay, but certainly not worth the $6 million he probably would have received.
Moves That Didn't
Picking up Cooper's option
Obviously, this was a pretty short-sighted move on Drayton/Ed's part. Perhaps this precipitated Cooper losing the clubhouse as the players realized they would likely be dealing with a lack of communication and questionable tactics for two more seasons. And while the Astros were never considered contenders, except for a two-week span in July, Astros players looked like they would rather be anywhere else except on the field in the second half.
Signing Mike Hampton
In 21 starts for the Astros in 2009 in which the Astros were 7-14, Hampton put up a 5.30 ERA / 1.55 WHIP in 112 IP. He allowed 13 homers, and had seven quality starts, compared to five disaster starts, and five starts in which he didn't make it out of the 5th inning. It was a low-risk, high-reward signing, but the Astros paid almost $300K per win.
Trading Jordan Parraz for Tyler Lumsden
The Astros sent Jordan Parraz to the Royals for Tyler Lumsden, a minor-league pitcher who was initially assigned to Round Rock. Except it didn't last. And Lumsden was sent down to Corpus on July 2. Lumsden was another "project pitcher" (see: Fulchino, Jeff) coming off Triple-A seasons in Omaha with ERAs of 5.88 and 7.21, respectively. He came to Round Rock, and put up a 4.42 ERA / 1.91 WHIP in 18.1IP, and 5.15 / 1.72 in 43.2IP in Corpus. And he's 26. Meanwhile, 24-year old RF Parraz ( 2004 3rd round pick) hit .358/.451/.553 for Double-A NW Arkansas, and .298/.358/.426 in Omaha.
Not re-signing Randy Wolf
By all accounts, Randy Wolf was open to coming back to Houston in 2009. The Astros allegedly had a 3-year $29.5 million offer on the table, then the economy tanked, and that offer was pulled. Wolf re-signed with the Dodgers for $5 million, and went 11-7 in 214.1 IP, with a 3.23 ERA / 1.10 WHIP. His 2.76 K:BB ratio was his highest since 2001, and his 2.4 walks/9 were his lowest since 2004. It's doubtful that Wolf would have taken a $24 million pay cut to come back, but it is what it is.
Anything I missed?