JAWS and the 2019 Hall of Fame Ballot: Roy Oswalt

The following article is part of Jay Jaffe’s ongoing look at the candidates on the BBWAA 2019 Hall of Fame ballot. It is based on earlier work done for SI.com. For a detailed introduction to this year’s ballot, and other candidates in the series, use the tool above; an introduction to JAWS can be found here. For a tentative schedule and a chance to fill out a Hall of Fame ballot for our crowdsourcing project, see here. All WAR figures refer to the Baseball-Reference version unless otherwise indicated.

Roy Oswalt spent a decade as one of the National League’s top pitchers before injuries took their toll. Though listed as just six feet tall and 180 pounds — size that caused him to be overlooked by scouts during his amateur days — he spent nearly a decade as a staple of the Astros’ rotation and a perennial Cy Young contender. Relying primarily on a mid-90s fastball/curve combination with an almost 20 mph differential, he never took home an award, or won a championship, but he played a key part on five postseason-bound teams in Houston and Philadelphia.

Had Oswalt enjoyed better luck in the health department, his career probably would have been the subject of spirited debate on, say, the 2024 Hall of Fame ballot. Alas, lower back woes caused by a pair of degenerative discs curtailed Oswalt’s major league career. His last effective season was in 2011, his age-33 season, and he threw his last pitch one month past his 36th birthday. His total of 2,245.1 innings is fewer than those of all but one Hall of Fame starter — and no, it’s not Sandy Koufax, it’s Dizzy Dean. While he may not truly be a viable candidate, he’s on a separate tier from the one-and-dones whom I’ll cover in brief later in this series.

Born in Kosciusko, Mississippi on August 29, 1977, Oswalt grew up in nearby Weir, a tiny town with a population of just 550. His father Billy Joe, a logger and rec league softball player, saw his son excel in Little League and eventually petitioned the school board to start up a baseball program at his high school, Weir Attendance Center; Billy Joe volunteered to clear pine trees for a ball field using his own equipment. Looking to get every advantage he could out of his small stature, the younger Oswalt came up with an unorthodox delivery. From a 2006 profile for ESPN Magazine by Buster Olney:

Because he was so slightly built, he had to use everything he had to propel the baseball-arm, legs, soul.

Young Roy had seen enough to know that most pitchers start their delivery with one foot parallel to the rubber. This made no sense to him. He was trying to drive himself toward the batter, like a sprinter breaking out of the blocks. Sprinters, he thought, don’t plant their feet parallel to the starting line; their feet are pointed forward.

So that’s how Oswalt designed his pitching mechanics, with his back foot, his right foot, angled slightly forward. He raises his left foot, pauses slightly, then hurls his body at the batter, more like a javelin-tosser than a sprinter in the end. Nobody else in the majors uses mechanics like these, and no pitching coach would teach them unless he was considering a change of profession. But batters have confessed that Oswalt’s motion can be unnerving, this wiry six footer leaping at them like a mugger.

Though he eyed a scholarship to Mississippi State, the 5-foot-10, 150-pound Oswalt struggled to get the attention of scouts in high school. He spent a year at Holmes Community College, but after growing two inches and pushing his fastball from 85 mph to 95, he was chosen in the 23rd round by the Astros in 1996 as a draft-and-follow. He signed with the Astros in May 1997 and pitched his way up the ladder, though an elbow sprain limited him to 15 starts in 1998 and shoulder soreness limited his effectiveness the following year. A month after the season, Oswalt was convinced he’d suffered a tear in his shoulder, in so much pain that it was affecting his sleep. And then — as he told ESPN’s Alan Schwartz in 2003:

I was outside working my truck, checking the sparkplug wires. I grabbed this one sparkplug wire, and the truck started, and the current just started shooting bolts through me. That made the muscles in my hand tighten up, so I can’t let go of this thing. I was holding on to it for what felt like two days, but it was probably just a minute. I couldn’t let go. Finally my foot slipped off the bumper and I got thrown off.

When I got up, my arm felt better. I went home and told my wife, ‘You’re never gonna believe what just happened.’ About a week later I couldn’t feel any pain in there at all. And I haven’t since.

Trainers speculated that the shock cleared out scar tissue in Oswalt’s shoulder. Whatever happened, in 2000 he struck out out 188 in 175 innings split between High-A and Double-A, became the first pitcher in 10 years to post an ERA below 2.00 in the hitter-friendly Texas League, and played a key role on the Team USA’s gold medal-winning Olympic team, throwing six strong innings against South Korea in the semifinals. His season vaulted him onto Baseball America’s Top 100 Prospects list at number 13. He made just five starts at Triple-A New Orleans before the Astros recalled him. He debuted on May 6, 2001 with an inning of garbage-time relief against the Expos; Vladimir Guerrero was his first strikeout victim.

The 23-year-old Oswalt made eight relief appearances before joining the rotation in June. He quickly found success, twirling six innings of two-hit, one-run ball against the Dodgers in his first start, and finishing the year 14-3 with a 2.73 ERA, 9.1 strikeouts per nine, and three complete games including a seven-hit shutout of the Brewers on September 7. His performance, worth 4.7 WAR (eighth in the league) helped the Astros win the NL Central, but he did not pitch during their three-game Division Series sweep by the Braves. He did finish second in the NL Rookie of the Year voting behind Albert Pujols, and fifth in the NL Cy Young voting despite throwing just 141.2 innings.

That outstanding rookie campaign was no fluke. In 2002, Oswalt made 34 starts and went 19-9 with a 3.01 ERA (fifth in the league), 8.0 strikeouts per nine (eighth), and 7.0 WAR (third). That was the beginning a nine-season stretch during which he averaged 208 innings with a 3.21 ERA (133 ERA+), 7.3 strikeouts per nine, and 4.9 WAR. Within that span, he placed in the top four in Cy Young voting four times (topping out in third place in 2004 behind teammate Roger Clemens and Randy Johnson), earned All-Star honors three times, and led the league in wins (20 in 2004), ERA (2.98 in 2006) and WAR (6.7 in 2007) once apiece. He had five top-five finishes in WAR during that span, and five in the top 10 in ERA. Only in 2003, when a recurrent groin strain sent him to the disabled list three times and limited him to 20 starts, did he fail to make 30 starts. Only once during that stretch did he post an ERA above 3.54.

Joined by free agents Clemens and Andy Pettitte, Oswalt helped the “Killer B” Astros – starring Jeff Bagwell, Craig Biggio, Lance Berkman, and (briefly) Carlos Beltran — win the NL Wild Card in 2004. Minus Beltran, and for the most part the injured Bagwell, they overcame a 15-30 start and won the NL pennant the following year. Fittingly, Oswalt earned 2005 NLCS MVP honors with a pair of seven-inning, one-run outings against the Cardinals, who had ousted them (and him) in a seven-game series the year before. The second of those two starts helped the Astros clinch their first pennant in the franchise’s 44-season history and earned Oswalt an unusual bonus: a Caterpillar D6N XL bulldozer, a gift promised to him by Astros owner Drayton McLane. “This is a dozer you can do anything with,” Oswalt said upon receiving his bonus that winter.

“We’ve achieved a great historical milestone,” said Astros general manager Tim Purpura while joking that that the team made baseball history by placing the first “bulldozer clause” into a contract.

Alas, in Oswalt’s lone World Series start, the White Sox cuffed him for five runs in six innings, and 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 Biggio in particular — had entered its decline phase. After winning just 73 games in 2007, the team climbed back to 86 wins the following year, but that was the aberration in the slide that led to their drastic rebuilding effort following McLane’s sale of the team to Jim Crane in the winter of 2011-2012. 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. Two days later, Berkman was traded to the Yankees.

In Philadelphia, Oswalt joined the two-time defending NL champions and a rotation that already featured Halladay and Cole Hamels. Oswalt was stellar upon his arrival, going 7-1 with a 1.74 ERA and 3.3 WAR in just 82.2 innings (compared to 2.7 WAR in 129 pre-trade innings). His performance helped the Phillies win the NL East and advance to the NLCS before being ousted by the Giants. Despite allowing one earned run apiece in his two NLCS 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 the Phillies were eliminated.

The Phillies signed free agent Cliff Lee — whom they’d traded to Seattle just a year prior — in December 2010, creating a four-ace rotation that helped the team win a franchise-record 102 games and their fifth straight division title. However, the degenerative disc condition in his lower back sent Oswalt to the disabled list for two stints totaling seven weeks, limiting him to 23 starts with a 3.69 ERA and 2.1 WAR. The Phillies 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 that marked the beginning of the end of his fine career, Oswalt signed with the Rangers, making for a very chaotic first day on the job for SI.com’s new baseball blog.

The Rangers appeared to be well on their way to their 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 very 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 .384 batting average on balls in play. After a strong debut, he made 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 sorry showing that served as something of a metaphor for a hot-starting team that lost the division to the A’s on the final day of the season and then was ousted in the Wild Card game.

Despite finishing the season with a 5.80 ERA, Oswalt was willing to take one last shot. He signed with the Rockies on May 2, but was clobbered for an 8.63 ERA in six starts and three relief appearances, and lost two months to a hamstring strain. Just before Christmas in 2013, he and Berkman agreed to sign one-day contracts with the Astros and retire together, which they did the following April.

…

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. In fact, his 51.2 WAR from 2001-2011 ranked second in the majors behind Halladay (65.5), just ahead of two-time Cy Young winner Johan Santana (50.7). Oswalt’s 2,154 innings and 133 ERA+ in that span both ranked eighth in the majors (using a 1,000-inning minimum for the latter), while his 1,759 strikeouts ranked fifth.

Alas, with “only” 163 career wins, 1,852 strikeouts, no championship rings and no Cy Youngs, Oswalt almost certainly won’t wind up in the Hall of Fame, hardly surprising for a pitcher throwing less than 100 innings after his age 33 season. Here it’s worth noting that while there are eight Hall of Fame starters with fewer than 200 wins and 11 with fewer than 3,000 innings — counts that both exclude pitcher-turned-shortstop Monte Ward — only Dean and Addie Joss had fewer wins than Oswalt (150 and 160, respectively), and only Dean had fewer innings (1,967.1). If you want to get elected to the Hall despite having a small body of work, it helps to be a folk hero.

Like Halladay, whose case I explored here, Oswalt only had eight seasons in which he pitched enough innings to qualify for the ERA title. Yet in six of those eight, he ranked among the league’s top 10 in WAR, and as noted, in five of those, he ranked among the top five. While he’s well off the Hall of Fame career standard in WAR (50.1 for Oswalt, 73.9 for the average enshrined starter), his 40.3 peak score is “only” 10 wins short and ranks 92nd all time, tied with Hall of Famer Red Ruffing and ahead of 15 of the other 62 enshrined starters, including the BBWAA-elected John Smoltz, Bob Lemon, Early Wynn, Herb Pennock, Catfish Hunter, Whitey Ford, and Don Sutton. Oswalt’s peak score is also higher than the still-active Chris Sale, CC Sabathia, Felix Hernandez, and Hamels — pitchers whose progress towards Cooperstown I’ve monitored here at FanGraphs, and ones whose constrained workloads might force voters to reassess their expectations for Hall-worthy pitchers.

Most of those Hall of Fame pitchers with lesser peaks than Oswalt had greater longevity. Oswalt’s 45.2 JAWS ranks 101st all-time and is ahead of just 13 Hall of Famers, of whom only Dean, Lemon (whose career was delayed by military service), Pennock, and Hunter were elected by the BBWAA. He’s also 10 spots below Pettitte (60.3 career WAR/34.1 peak WAR/47.2 JAWS), who in turn trails Clemens, Schilling, Mussina, and Halladay among current candidates.

As I noted at the time of his retirement, 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 stood just six feet tall as well. His 48.4 WAR for the decade (1980-1989) dwarfed the field, but he spent his career in the shadow of Clemens and 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% of the vote in his lone appearance on the 2004 BBWAA ballot, Stieb is still revered by baseball fans of a certain age. Oswalt, who’s been included on just one of the first 71 ballots published, is likely to be remembered the same way: as a great pitcher for whom the stars never quite aligned to allow him his due. It’s an impressive career nonetheless.