How dealing Oswalt sparked Astros' turnaround

HOUSTON -- With the Astros on the decline on the field and owner Drayton McLane on the verge of selling the club a decade ago, star pitcher Roy Oswalt saw the writing on the wall. Oswalt, the workhorse of the Houston rotation for nearly a decade, asked to be traded in the middle of the 2010 season.

It was only five years after the Astros made their first World Series in 2005 and less than two years after they narrowly missed the playoffs in ’08. Still, Houston’s roster was aging and a barren farm system meant there wasn’t much reason for optimism. And with McLane itching to sell, Oswalt was dealt to the Phillies on July 29, 2010 in exchange for J.A. Happ, Jonathan Villar and Anthony Gose, who was flipped to Toronto for Brett Wallace.

That was only the start. Two days after trading one of the greatest starting pitchers in franchise history, the Astros dealt one of the best hitters in club history by sending Lance Berkman to the Yankees for Mark Melancon and Jimmy Paredes. The Astros’ rebuild was full-steam ahead.

McLane eventually sold the club to Houston businessman Jim Crane after the 2010 season for $680 million -- contingent upon Houston moving to the American League beginning in 2013 -- and Crane hired general manager Jeff Luhnow from the Cardinals to oversee the rebuild. He dealt away any player whose contract had value to stockpile prospects to help rebuild the system.

Consecutive 100-loss seasons came in 2011 and ’12, and the Astros bottomed out in ’13, during which the team payroll was $13 million. They lost a franchise-record 111 games. In the Minor Leagues, though, the franchise was slowly turning around.

Following the Oswalt and Berkman deals in 2010, here’s how the Astros traded away the remaining core of their franchise for four consecutive years at the Trade Deadlines in exchange for prospects, and a look at which deal signaled the rebuild was over.

2011
On the move: In the span of 12 days in late July, the Astros traded veterans Jeff Keppinger (Giants), Hunter Pence (Phillies) and Michael Bourn (Braves) in exchange for 10 prospects.

Breakdown: Keppinger (José Altuve) and Pence (J.D. Martinez) were replaced by prospects who were future All-Stars, but none of the Minor League players the Astros acquired in any of the deals provided much value. The Astros gave slugger Jonathan Singleton, acquired from the Phillies, $10 million before he reached the big leagues, but he turned out to be a huge bust. The four players Houston got from the Braves combined for a 0.7 WAR during short Major League stints in Houston.

2012
On the move: Slugger Carlos Lee, whose six-year, $100 million contract -- then a club record -- and apparent lack of physical fitness made him an unpopular player in Houston despite three consecutive 100-RBI seasons, was dealt to the Marlins for infielder Matt Dominguez and pitcher Rob Rasmussen on July 5. At the end of the month, the Astros traded away veteran pitchers Happ (Blue Jays), Brandon Lyon (Blue Jays), Brett Myers (White Sox) and Wandy Rodriguez (Pirates), and veteran infielder Chris Johnson (D-backs).

Breakdown: Dominguez was a solid defensive third baseman who started at the position in 2013 and ’14 but was a below-average offensive player. The Astros got some value from the Blue Jays by acquiring starting pitcher Joe Musgrove in a seven-player haul, and future All-Star reliever Chris Devenski was the player-to-be-named in the Myers deal. Of the three players the Astros got for Rodriguez, only Robbie Grossman made any impact in the big leagues.

2013
On the move: Right-hander Bud Norris, who was the Astros’ highest-paid player at $3 million, was dealt to the Orioles in exchange for Minor League outfielder L.J. Hoes and reliever Josh Hader on July 31. Two days prior, veteran reliever Jose Veras was dealt to the Tigers.

Breakdown: Hoes posted a paltry 75 OPS+ in parts of three seasons in Houston, and the Astros dealt Hader -- a future All-Star -- to the Brewers two years later in the deal that brought in Carlos Gómez and Mike Fiers. The Astros’ return for Veras wasn’t good: outfielder Danry Vasquez and pitcher David Paulino. Vasquez was placed on administrative leave by MLB and later released by the Astros in 2016 after being arrested on suspicion of domestic violence while at Double-A. Paulino reached the big leagues but saw his career derailed by a PED suspension ’17.

2014
On the move: In the middle of their first non-100-loss campaign since 2010, the Astros traded Jarred Cosart, infielder/outfielder Enrique Hernández and Minor League outfielder Austin Wates to the Marlins for outfielder Jake Marisnick and two Minor Leaguers: pitcher Francis Martes and third baseman Colin Moran.

Breakdown: Marisnick became an established outfielder for five seasons in Houston, helping the club win the World Series in 2017 before he was traded to the Mets in December 2019. Martes developed into a top prospect in Houston's system and reached the big leagues before two drug suspensions and Tommy John surgery derailed his career. Moran reached the big leagues, and he was later dealt to the Pirates in the Gerrit Cole deal.

Change of course
With the farm system among the best in the game and the Major League club on the uptick, the Astros changed course. After the 2014 season, they acquired catcher Hank Conger from the Angels in exchange for Minor League pitcher Nick Tropeano and Minor League catcher Carlos Pérez. It certainly wasn’t a memorable deal at the time, and still isn’t even more than five years later. But it marked the first time since Luhnow took over prior to the ’12 season that the Astros had acquired a veteran in exchange for prospects. The rebuild was ending.

In the weeks that followed, the Astros signed free-agent relievers Pat Neshek and Luke Gregerson and infielder Jed Lowrie, acquired Evan Gattis from the Braves and Luis Valbuena from the Cubs and signed Colby Rasmus. With top prospects Carlos Correa and Lance McCullers Jr. making their debuts in 2015, the Astros, behind first-year manager AJ Hinch, made the playoffs that season and won the World Series two years later. A juggernaut was born, but it certainly didn’t happen overnight.