Longtime Astros ace Oswalt to retire after stellar career

Roy Oswalt pitched 10 of his 13 seasons for Houston. (Brad Mangin/SI)

Roy Oswalt, who spent a decade as one of the National League’s top pitchers before injuries took their toll, has decided to retire. Once a perennial Cy Young contender and a staple of the Astros’ rotation, over the past two seasons the 36-year-old righty has pitched in the majors only sporadically and largely ineffectively. In stints with the Rangers (2012) and Rockies (2013), he was unable to regain the form that might have allowed him to be part of a championship team and to make a serious bid for future election to the Hall of Fame.

The pitcher told the Houston Chronicle that he and longtime former teammate Lance Berkman plan to sign one-day contracts with the Astros at some point in the future and formally retire together. The pitcher will remain in the game by working as the vice president of baseball operations for RMG Baseball, the company founded by his former agent Bob Garber.

Oswalt burst onto the major league scene in 2001, when he went 14-3 with a 2.73 ERA in 20 starts and eight relief appearances. By that point, he’d already beaten long odds. A native of tiny Weir, Miss., (population 550), he had struggled to get the attention of scouts as a prep player due to his lack of size (5’10″, 150 pounds in high school). He had set out for Holmes Community College with an eye toward a Mississippi State scholarship, but after growing two inches and pushing his fastball from 85 to 95 mph, he was chosen in the 23rd round by the Astros in 1996 as a “draft-and-follow.” The bygone rule allowed a team to see how a lower-round pick fared during his next college season before the team made a full commitment to him. Oswalt signed with Houston in May 1997 and pitched his way up the ladder. After helping Team USA win a Gold Medal in the 2000 Olympics in Sydney, Australia, he entered the 2001 season ranked 13th on Baseball America‘s Top 100 Prospects list.

The 23-year-old Oswalt made his major league debut on May 6, 2001 as a reliever. He pitched out of the bullpen eight times before joining the rotation in early June; in his first start, he twirled six innings of two-hit, one-run ball against the Dodgers. Despite throwing just 141 2/3 innings that year, he placed fifth in the Cy Young voting and was runner-up in the NL Rookie of the Year balloting behind Albert Pujols.

His outstanding rookie campaign was no fluke. The next year, Oswalt made 34 starts and went 19-9 with a 3.01 ERA and 8.0 strikeouts per nine (down from a sizzling 9.1 as a rookie). That was the first year of a nine-season span in which he averaged 208 innings with a 3.27 ERA (132 ERA+), 7.2 strikeouts per nine and a stellar 3.4 strikeout-to-walk ratio. He earned All-Star honors three times in that span, led the league in wins (in 2004, with 20), ERA (2006, with a 2.98) and Wins Above Replacement (2007, with 6.7) once apiece, and placed in the top four in the Cy Young balloting four times. He made at least 30 starts in every year in that span except 2003, when a recurrent groin strain sent him to the disabled list three times and limited him to 20 starts. Despite pitching half his games at hitter-friendly Minute Maid Park during a high-scoring era, he had only one season in that stretch with an ERA above 3.54.

Joined by free agents Roger Clemens and Andy Pettitte, Oswalt helped the Astros win the NL wild card in 2004 and the NL pennant the following year. Fittingly, he earned 2005 NLCS MVP honors with a pair of seven-inning, one-run outings against the Cardinals, who had ousted them (and him) in an epic seven-game series the year before. The second of those two starts in ’05 helped Houston clinch the first pennant in the franchise’s 44-season history. Alas, the White Sox cuffed him for five runs in six innings in his lone World Series start, and they finished their four-game sweep the next night.

Oswalt signed a five-year, $73 million extension in August 2006, passing up an opportunity to test free agency after the 2007 season, when he would have been 29 and primed for even bigger bucks. Unfortunately for him, the Astros’ core — Oswalt, Berkman and Craig Biggio in particular — had entered its decline phase. After sinking to 73 wins in 2007, the team rose back to 86 the following year, but that was the aberration in the slide that led to their drastic rebuilding effort following owner Drayton McLane’s sale of the team to Jim Crane in the winter of 2011-12. On July 29, 2010, Oswalt agreed to waive his no-trade clause and accepted a trade to the Phillies in exchange for J.A. Happ, Jonathan Villar and Anthony Gose, the latter of whom was flipped to the Blue Jays for Brett Wallace.

In Philadelphia, Oswalt joined the two-time defending NL champions and a rotation that already featured Cole Hamels and Roy Halladay. Oswalt was stellar upon his arrival, going 7-1 with a 1.74 ERA while helping the team win the NL East and advance to the NLCS before being ousted by the Giants. Despite allowing one earned run apiece in his two starts, Oswalt had a rough series; in a rare relief appearance in the ninth inning of a tied Game 4, he yielded the winning run, and he wound up on the short end of a 3-2 decision in Game 6 as Philadelphia was eliminated.

The Phillies reacquired Cliff Lee that winter, creating a four-ace rotation that helped the team win 102 games and their fifth straight division title in 2011. However, a degenerative disc condition in his lower back sent Oswalt to the DL for two stints totaling seven weeks, limiting him to 23 starts with a 3.69 ERA. Philadelphia declined his $16 million option at season’s end, and he made the unconventional decision to wait until mid-2012 before signing a new contract, thereby maximizing his leverage and scaling back his workload. On the same day that Halladay hit the DL with shoulder woes, Oswalt signed a $5 million deal with the Rangers, making for a very chaotic first day for SI.com’s new baseball blog.

The Rangers appeared to be well on their way to a third straight AL West flag — and perhaps a third straight AL pennant — at the time Oswalt signed, but it turned out that he wasn’t all that much help. Though he struck out 59 hitters while walking just 11 in 59 innings, he was battered for 11 homers as well as a .447 batting average on balls in play. After a strong debut, he managed just one quality start out of his next five before being pushed to the bullpen, a role he despised. On one occasion, he refused to continue pitching after throwing two perfect innings, a showing that served as something of a metaphor for a hot-starting team that fizzled, losing the division to the A’s on the final day of the season and then being ousted in the Wild Card Game.

Despite finishing the year with a 5.80 ERA, Oswalt was willing to make one more go of it. He signed with the Rockies last May 2, but he was clobbered for an 8.63 ERA in six starts and three relief appearances, while losing two months to a hamstring strain.

Oswalt never won a Cy Young award, but there’s little question that he belonged on the short list of the game’s best pitchers for more than a decade. From 2001-2011, only Halladay outdid his 51.1 WAR. Oswalt’s 2,154 innings and 133 ERA+ in that span both ranked eighth in the majors, his 1,759 strikeouts fifth.

With “only” 163 career wins, no championship rings or other hardware, Oswalt isn’t likely to wind up in the Hall of Fame, hardly surprising for a pitcher who threw less than 100 innings after his age-33 season. Neither his 50.1 career WAR or his 40.0 peak WAR (best seven seasons) are close to the JAWS standards among starting pitchers (72.6 WAR and 50.2 WAR, respectively). His 45.1 JAWS places him just 99th all-time, ahead of 27 of of the enshrined 57 starters but still 16 points shy of the standard. Given the glut of non-300 win pitchers on the ballot now or in the coming years (Mike Mussina, Curt Schilling, Pedro Martinez, John Smoltz and Halladay), it’s unlikely the BBWAA voters will view a pitcher with less than 200 wins favorably enough to grant him entry.

In the end, Oswalt’s career has a whole lot in common with that of former Blue Jays ace Dave Stieb. Arguably the best pitcher of the 1980s, Stieb’s 48.1 WAR for the decade (1980-89) dwarfed the field, but he spent his career in the shadow of Clemens and Jack Morris, among others, and never won a Cy Young. Back woes prevented Stieb from making more than 20 starts in any year after his age-32 season (1990), and he walked away at age 36, sitting out four years before attempting a brief comeback with Toronto in 1998. The tale of the tape:

Though he garnered just 1.4 percent of the vote in his lone appearance on the BBWAA ballot, Stieb is still revered by baseball fans of a certain age. Oswalt is likely to be remembered the same way: as a great pitcher for whom the stars never quite aligned so that he could get the acclaim that was fully his due.