Ranking the 15 Worst Signings in Houston Astros History

The Houston Astros run of dominance over the last six seasons has been filled with key acquisitions and free agent signings that have gone on to play massive roles. Established names like Michael Brantley have played a key role, as have reclamation projects like Will Harris and Collin McHugh.

For every great acquisition, there are plenty of bad ones. As much as the Golden Era makes it easy to forget, the Astros historically haven't been a dominant franchise, and they've had their fair share of swings and misses in free agency over the years. Let's take a look at the 15 worst signings in Astros history.

15) Justin Verlander-2 years, $66 million

What?! How can one of the best pitchers in the history of the franchise make this list?

Well, let's think about this. Justin Verlander arrived at the 2017 waiver deadline and was dominant in Houston. The Astros rewarded Verlander before the 2019 season with a two year, $66 million extension to cover the 2020 and 2021 seasons.

Verlander threw six innings in those two seasons. He was injured in his first start of the COVID-shortened 2020 season and missed all of 2021 after undergoing Tommy John.

Yes, he was dominant from 2017-2019. Yes, he won the Cy Young in 2022. That does not change that he received $11 million per inning worked in a two-year span. Seeing as Houston came within a game of the World Series in 2020, lost the World Series in 2021 and won in 2022 with Verlander scuffling his way through the postseason, could the $33 million Houston gave Verlander have been better suited in retaining George Springer? Or maybe they offer an earlier extension to Altuve, Bregman or Tucker with the money.

This contract would be much higher on this list than it is had it been a free agent signing rather than an extension or had he walked after 2021. That he returned in 2022 keeps it lower on the list.

14) Carlos Lee-6 years, $100 million

The first two entries on the list also happen to be the two best players to appear on the list. El Caballo was great during his stint in Houston and earned the money they gave him. That he appears on this list is no fault of his own.

During his time in Houston, Lee hit .286 with an .817 OPS. He appeared in all 162 game the first year of his contract and drove in 533 runs in the 815 games he appeared in. So how does Lee make this list?

The six years, $100 million Houston gave him in 2007 is the type of money the Astros balk at fifteen years later under a more aggressive owner. It backfired immensely on the Astros, as they were able to surround the slugger with virtually no help, missing the playoffs all six seasons. Lee's deal is similar to the deal the Rockies gave Kris Bryant while simultaneously not even attempting to be competitive.

One man can't make a team win in the MLB. Just ask Mike Trout. Jeff Luhnow went on to trade Lee in the final year of the deal, jump starting the Astros' rebuild that led to the golden era of today.

13) Preston Wilson-1 year, $4 million

The Astros signed Preston Wilson in 2006 in an attempt to bolster their offense that struggled in the 2005 World Series. Wilson agreed to a uniquely structured deal, signing for one year and $4 million. Houston would then have to decide after the season whether to extend Wilson for three years and $24 million, or buy the veteran out.

Though Wilson was not bad in an Astros uniform (.269 average and .714 OPS), he couldn't match the offensive levels he had produced in the previous nine years, Houston cut their ties after only 102 games, releasing Wilson after being unable to find a trade partner.

12) Bill Hall-1 year, $3.25 million

The Astros signed Bill Hall in 2010 to be their everyday second baseman. This was a result of a later to appear on this list signing that had woefully failed in the role.

Hall had been tremendous in a super-utility role for the Boston Red Sox in 2010, recording a .772 OPS and playing a multitude of possessions. Hall lasted only 46 games with the Astros, hitting .224 with a .612 OPS.

The Astros released Hall in the middle of June, still searching for their everyday second baseman, a role that Jose Altuve would of course go on to fulfill.

11) Brandon Lyon-3 years, $15 million

The Astros gave Brandon Lyon three years and $15 million to be their closer. While Lyon wasn't bad in the 37 appearances he made for the Astros, he only made 37 appearances and recorded zero saves.

Lyon was sent out as part of a 10-player trade in the first year of his contract. The rationale behind this inflated signing still doesn't make sense.

Was he not at least a solid contributor during his time in Houston, he'd be much higher on the list.

10) Shawn Chacon-1 year, $2 million

Though not an expensive signing, the Shawn Chacon deal was an abject failure in Houston. Chacon chose to sign in Houston because they would let him start after he had fluctuated between starter and reliever.

In the 15 starts Chacon made in Houston, he racked up a 5.04 ERA and a 1.50 WHIP.

The numbers themselves are terrible. Then let's account for off the field.

Chacon assaulted then general manager Ed Wade, grabbing him by the neck and throwing him to the ground after being removed from the starting rotation. Chacon was waived the next day and never again played in the big leagues.

9) Pedro Feliz-1 year, $4.5 million

The Astros signed Pedro Feliz to a one year, $4.5 million deal to be a platoon third baseman. He lasted only 97 games in Houston. He hit an abysmal .221 with a .555 OPS, racking up a -2.0 bWAR.

Houston wasted no time punting on the experiment, trading Feliz midway through the season. Safe to say the platoon idea was not one for the long haul.

8) Tony Sipp-3 years, $18 million

Tony Sipp was a revelation in the 2015 season, posting a microscopic 1.99 ERA. The Astros rewarded him with a three-year, $18 million deal.

The results of said deal were…not great. Sipp posted a 4.95 ERA with a 1.6 WHIP in the 2016 season. The 2017 season was even worse for Sipp, with his ERA ballooning to 5.79. Though he regained form in 2018, that is not enough to offset his abysmal first two years.

Sipp played one more year in 2019 with the Washington Nationals. 

7) Gregg Zaun-2 years, $2.35 million

Gregg Zaun signed a two-year, $2.35 million deal in Houston. Zaun had proven himself as an offensive backstop, racking up a .727 OPS in his seven big league seasons before Houston.

He never came close to touching those numbers as an Astro. Zaun hit .220 with a .596 OPS as an Astro. These numbers are a far cry from his career OPS of .732. 

His failures are rather perplexing, as he was at least a neutral player every other stop he made during his 16-year career, but he was a -1.4 bWAR player as an Astro.

Had he been tasked with being an everyday player rather than splitting time with Brad Ausmus, it's likely Zaun finishes even higher on the list.

6) Kaz Matsui-3 years, $16.5 million

The Astros gave Kaz Matsui three years and $16.5 million to replace Craig Biggio as the everyday second baseman. Matsui went on to hit .259 with a .685 OPS in three years in Houston.

Needless to say, Matsui did not match Biggio’s production in Houston.

The Astros released Matsui in the third year of the deal, when he had racked up a -0.8 bWAR in only 27 games.

The mid-2000s to early 2010s were a nightmare time in Houston, with inflated deals for underachieving players the standard operating procedure,

5) Omar Moreno-5 years, $3.25 million

Houston gave Moreno five years and $3.25 million with hopes the defensive centerfielder could regain some semblance of offensive form.

Moreno didn't regain any offensive form and was traded after only 97 games. In his time as an Astro, Moreno hit .242 with a .608 OPS, the worst year of his big league career.

That the Astros pledged that length of contract to the outfielder before sending him out only one year in was simply astounding. His on field perfomance was subpar and it's rumored he became a bit of a problem in the clubhouse. The $700,000 Houston pledged to Moreno annually couldn't have backfired more than it did.

4) Dave Roberts-5 years, $1.3 million

The Astros gave Dave Roberts five years in hopes he would fill a super utility role for them moving forward. Very rarely do teams find a player than can play both catcher and shortstop.

Sadly for Houston, they realized Roberts couldn't play any of the utility spots very well. In 27 games as an Astro, Roberts hit .241 with a .623 OPS. Though the season was shortened by a strike, Roberts was very poor in the time he was able to set foot on the field.

Houston traded Roberts the following spring training, though they still had to pay him. Talk about a worst case scenario.

3) Woody Williams-2 years, $12.5 million

The Astros committed $12.5 million to Woody Williams in 2007 hoping he would replace names like Roger Clemens and Andy Pettite in the rotation. Simply put, he didn't. Williams last only one of the two years on the deal, with the 40-year-old posting a 5.27 ERA and a 1.43 WHIP.

After Williams posted an 11.32 ERA in spring training in his second year in Houston, the Astros gave him his release, still on the hook for $6.25 million.

The Astros had absolutely no business committing that money to a 40-year-old with a 4-plus ERA for his career. The signing was one of the biggest misses in franchise history.

2) Greg Swindell-4 years, $17 million

The Astros signing of Greg Swindell couldn't have gone worse. Through the first seven years of his career, Swindell had a 3.60 career ERA. During his four years in Houston, his ERA swelled to a 4.48. Swindell signed with great expectations and failed to meet all of them.

Swindell was a negative bWAR player during his time in Houston, but was good for over 30-bWAR in the other 13 years in his career. He just couldn't handle the pressure of the deal. Houston moved on in year four of the deal, with Swindell carrying a 7.83 ERA through eight games, including a demotion to the bullpen.

Were it not for one worse signing, this would be the worst signing in franchise history.