Ranking the 7 biggest free agent signings in Astros history

The Astros signing of Josh Hader continues to be huge news in Houston. Such a drastic change of protocol regarding free agency and the CBT remains hard to believe. After being reluctant to spend big money in free agency, and never giving out a free agent contract longer than four years, Houston gave Josh Hader five years and $95 million, making him the richest closer in MLB history.

Hader immediately becomes one of the biggest signings in franchise history. Barring an out of nowhere collapse at 29 years old, Hader should be a dominant arm for the remainder of his contract. Assuming he lives up to his 2.50 career ERA, he will be one of the best signings Houston has ever made.

So let's take a look at the other huge moves Houston has made in free agency. There aren't a ton, and for all of the criticism lobbed Jim Crane's way about not spending, most of the splashes they have made have come under his regime.

Ranking the 7 biggest free agent signings in Astros history

Let's start with the richest deal Houston has ever handed out.

No. 7: Carlos Lee

Heading into the 2007 season, Carlos Lee signed with the Astros for six years and $100 million. To this day, the Astros have never given a free agent a more expensive contract. Houston had just missed the playoffs in 2006 and signed Lee to bolster their offense.

For the first three years of his deal, he did just that. From 2007-2009, Lee hit .305 with 86 home runs, 321 RBI and an .878 OPS. He stumbled a bit in 2010 before rebounding in 2011.

Lee was shipped out in 2012 at 36 years old to the Marlins as the Astros entered their now famous rebuild under Crane and Luhnow.

All told, Lee hit .286 with 133 home runs and an .817 OPS during his Astros tenure. The Astros missed the playoffs in all six of Lee's seasons in Houston. Lee lived up to his end of the deal, but his contract did hamstring the organization quite a bit, and they never really surrounded him with the needed talent to win.

That said, it's the richest deal they've ever given out and he performed around at least an All-Star level in four of the six seasons. It's definitely one of the biggest signings Houston has ever made.

No. 5: Josh Hader

Josh Hader hasn't thrown a pitch for the Astros yet and he's already one of the biggest signings in franchise history. He's arguably the best closer of his generation, with career marks of a 2.50 ERA, 0.94 WHIP, 165 saves, and an almost unfathomable 15.0 SO/9.

He was the top reliever on the market in 2023, and was never seriously linked to Houston for much of the free agent period, and for good reason. The Astros simply don't spend on top free agents and they don't give out long-term contracts. A top free agent, of course, is looking for high dollars and contract security.

That the Astros gave Hader both of these things is massive. He's one of the filthiest arms in the game, and beyond that, teams about to enter a rebuild don't hand out contracts like the Astros just gave Hader.

For all of the chatter about the title window getting ready to close after 2024, is the Hader signing emblematic of the Astros turning a page and deciding to begin opening the checkbook with more regularity? It's entirely likely we look back on the signing of Hader as a sign of things changing with how the front office operates.

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.

No. 2: Roger Clemens

Roger Clemens, like Pettitte, spent three years in Houston. He came out of retirement to sign a one-year deal in 2004 before re-upping again in 2005. He then (what?! emerged from retirement once more, this time mid-season, in 2006. And you won't believe what he did the next summer at Yankee Stadium, either.

Clemens was otherworldly in his Houston tenure, going 38-18, recording a 2.40 ERA, winning one Cy Young, and somehow finishing third in 2005 (1.87 ERA, 226 ERA+, 2.87 FIP).

He made seven playoff starts across 2004 and 2005, and while he wasn't as dominant as he was in the regular season, he remained a huge piece of the Astros' first World Series trip in franchise history.

He already had a Hall of Fame resumé before signing in Houston, and landing a player of his caliber was the biggest splash the Astros had made in decades. 25 years, to be exact. Only one signing in franchise history was bigger than The Rocket.

No. 1: Nolan Ryan

In 1979, the Astros made Nolan Ryan the first million-dollar man in MLB history, signing him to a four-year, $4.5 million deal. The Ryan Express went on to spend nine years in Houston, going 106-94 with a 3.13 ERA and 2.87 FIP.

Ryan played in the era of baseball when the only metric that mattered for pitchers was wins, so he never received the award recognition he deserved in Houston as a result of playing for a mediocre team.

Only three times in his tenure did Ryan even finish top-10 in AL Cy Young voting, though he twice led the NL in ERA and strikeouts, and four times gave up the fewest hits/9 in the league. He threw his fifth no-hitter while with Houston, and also became MLB's all-time leader in strikeouts while playing for the Astros. In his first year in Houston, he led them to their first division title in franchise history.

The Astros retired Ryan's No. 34 in 1996, and he was of course a member of their inaugural Hall of Fame class in 2019.

The Astros made him the highest-paid player in big league history, and he continued to build on what was already one of the best pitching resumes in the history of the sport. There has been no greater signing in franchise history than Nolan Ryan.