Ranking the 7 biggest free agent signings in Astros history

No. 4: Andy Pettitte

Andy Pettitte was already one of the best postseason pitchers in MLB history before he joined the Astros. Houston signed the native Texan to a three-year deal heading into 2004, and he responded with a 3.38 ERA and a top-five Cy Young finish during his Houston tenure.

Pettitte was phenomenal in 2005, posting a 2.39 ERA across 33 starts, before playing a key role in the Astros making their first World Series trip in franchise history. He toed the rubber for four postseason starts, including six innings of two-run ball in the World Series.

His time with the Astros was short, but his signing was emblematic of the Astros going all-in to pursure a ring during the tail end of the Biggio/Bagwell era.

No. 3: Michael Brantley

Michael Brantley is undoubtedly one of the biggest signings in franchise history. Houston had already won one ring before signing Uncle Mike in 2019, but it's very likely they don't win a second without him.

Brantley was an elite on-field talent during his time in Houston, hitting .305 with an .828 OPS. Arguably more important than his hitting expertise was his leadership. Brantley took both George Springer and Kyle Tucker under his wings, mentoring both and helping them grow into elite players.

Even while battling injury and unable to play, he turned the 2022 World Series on its head. With the Astros down 2-1 after getting their doors blown off in Philadelphia in Game 3, Brantley delivered one of the greatest locker room speeches in sports history. The Astros responded, winning three straight to take home a second title.

From incredible diving plays to save an ALCS, to double after double in the gap, Brantley was a vital addition to their roster, and it's entirely plausible their Golden Era wouldn't have been prolonged without him.