Roy Oswalt to Retire: How Should Phillies Fans Feel About His time In Philadelphia?

Early Tuesday afternoon, 36-year old starting pitcher Roy Oswalt announced his retirement from professional baseball. The 13-year veteran, who spent the first 10 seasons with the Houston Astros, has decided to hang it up after failing to win a game during a comeback attempt last season with the Colorado Rockies. Oswalt officially retires with a 163-102 career record, 3.36 ERA, and 1852 strikeouts and a 5-2 postseason mark to go along with it. Oswalt also pitched in three straight All-Star games and has two career 20-win seasons.

During the 2010 season, the floundering Astros swapped Oswalt to the Philadelphia Phillies for a package centered around young left-handed starter J.A. Happ. The deal, which occurred days before the trade deadline, would be the second in back-to-back years that the Phillies swapped for a marquee starter during the season. In 2009, Cliff Lee nearly led the team to their second straight World Series with very little support within the team’s rotation. In 2010, Oswalt would be joining a staff that included eventual Cy Young winner Roy Halladay and a rejuvenated Cole Hamels. Oswalt’s 6-12 record at the time of the trade was more indicative of the talent-level surrounding him and his nifty 3.42 ERA was enough to convince the Phillies to part ways with one of their top prospects.

Oswalt backed up the Phillies show of good faith in his first extended time in Philadelphia during the 2010 season. He was sizzling down the stretch, posting a 7-1 record in 12 starts and helping the team clinch their fourth consecutive division title. With Halladay and Hamels preceding him in the playoff rotation, many felt the Phillies had constructed an ideal three-man cycle that would make them a near-impossible out in the postseason. This sentiment was only reinforced after the team swept aside the Cincinnati Reds in the NLDS with all three starters collecting victories.

Oswalt was a mixed bag following the NLDS win over the Reds. He was extremely impressive when he won game two of the NLCS against the Giants, only to drop his second start of the series in equally underwhelming fashion as the Phillies bowed out to the eventual World Series champs. Given the lackluster performances of the entire Phillies team during that series, it is tough to get on Oswalt’s case considering he actually won his start.

His career in Philadelphia took a rocky turn throughout the 2011 season. After being a model of dependability and durability over the course of his entire time as a pro, Oswalt started to show signs of aging. He missed an extended stretch of time early in the year, when a tornado damaged his hometown and he returned to help his family with the coping process. Oswalt then missed the entire month of July when severe back issues, something the pitcher had apparently dealt with over his entire career, actually put his immediate and long-term future in jeopardy. Ultimately, the projected fourth starter for the Phillies entering the postseason was up-and-down over the last couple months of the season, but had won enough to prove he could be part of the team’s playoff rotation.

After a stellar outing by Cole Hamels in game three positioned the Phillies to do away with the St. Louis Cardinals, Charlie Manuel handed the ball over to Oswalt with a chance to clinch. He was 3-1 in playoff starts against the Redbirds and the longtime Astro seemed like a reasonable choice to take the mound against his former division rival. One could have easily made the argument for sending Roy Halladay back out to avoid having the series go back to Philadelphia, but Oswalt was the call. Unfortunately, this game will be the only thing that ever defines Roy Oswalt’s career in Philadelphia from my standpoint.

After starting game four with a 2-1 lead, the two sides were mostly dormant throughout the early stages of the game. After falling behind 3-2 in the 4th inning, Oswalt returned to the game for the bottom of the fifth inning. During what would turn out to be a harmless at-bat by St. Louis infielder Skip Schumaker, the Phillies starter became noticeably shaken when a squirrel scampered across home plate. He ended up arguing balls and strikes with home plate umpire Angel Hernandez and, despite getting out of the 5th, Oswalt had let the scene get the best of him. He would give up an eventual game-winning two-run home run to David Freese and the Phillies would lose the game, and ultimately the series. Oswalt would never pitch again for the Phillies after the game four loss in St. Louis.

Looking back on things, the Phillies were not devastated from a prospect standpoint by their acquisition of Oswalt. Happ never turned out to be much more than a solid starter and none of the prospects included in the deal have amounted to much of anything. The most disappointing aspect of Oswalt is that he represents the peak of Ruben Amaro Jr.’s attempted style of winning a second world series for the Phillies. One of the ‘Four Aces’, an approach that was a tremendous recipe for regular season success, proved to be fruitless when the playoffs came around. Whether it was the heavy innings load each starter had to deal with over the 162-game schedule, the lack of big-game experience for the bullpen, or the lineup’s dependence on such stellar pitching the Phillies elimination from the 2011 playoffs still stands as the end of the most recent era of success in Philadelphia baseball.

Oswalt was an excellent pitcher during his prime and we caught the tail-end of it during his 1+ seasons in Philadelphia. However, Oswalt was the quintessential luxury purchase and for that, it’s tough not to have a sour taste in one’s mouth regarding his career with the Phillies. Hard to believe that of the three marquee acquisitions from the Astros organization over five years, Brad Lidge (not Oswalt or Hunter Pence) was the player who contributed the most toward the Phillies franchise.