Originally posted on Fangraphs  |  Last updated 10/7/11

Roy Halladay and Chris Carpenter were drafted by the Toronto Blue Jays within two years of each other in the early to mid 1990s. The two friends, and mountains of men, were supposed to front a talented Toronto rotation heading into the new millennium.

However, in quite the Pulsipher-Wilson-Isringhausen fashion, the desired results were not yielded. Expectations were lofty, but Halladay struggled with command — which sounds ridiculous but remains true — and Carpenter was unspectacular when healthy, and unhealthy rather frequently.

Following the 2002 season, the Halladay-Carpenter experiment ended. Unfortunately for the Blue Jays, it’s possible that one more year of patience would have benefited them greatly. That season marked the first when Halladay became Halladay, the eventual Hall of Fame pitcher that will undoubtedly go down as the best of this era.

Carpenter, meanwhile, made just 13 starts and spent three stints on the disabled list with shoulder troubles. His numbers were nothing to write home about — 5.5 K/9, 3.1 BB/9, 5.28 ERA, 4.67 SIERA — and the Blue Jays removed him from the 40-man roster after the season. Intrigued by his potential, the organization offered him an incentive-laden, minor league deal, but Carpenter turned them down. He hit free agency, and the rest is history.

He signed with the Cardinals the next season, hoping to return by the all star break, but ultimately missed the entire year with a torn labrum. In seven years as a major league pitcher, Carpenter had struggled to stay on the mound and the injuries were very concerning from a long-term production standpoint. The Blue Jays proved prescient in parting ways with Carpenter from an injury perspective, as he made just four major league starts in 2007-08. Where more diligence may have benefited them was evaluating his production prospects. Sure, working with Dave Duncan helped turn Carpenter into the pitcher typically worth 5 WAR over a full season, but the talent obviously existed before signing with the Cardinals.

Halladay and Carpenter have never matched up with one another, and for Blue Jays fans, the deciding game of the Phillies-Cardinals division series will serve as a reminder of what could have been. For both Cardinals and Phillies fans, having Carpenter and Halladay toe the respective rubbers gives each team its best chance of advancing. Halladay is a better pitcher, but the Cardinals have been more impressive at the plate this series, and Carpenter is no slouch. He struggled in Game Two, when he allowed four runs in the first two innings while pitching on short rest. Friday night, he’ll throw on full rest, and it will be tough for the Phillies offense to pound him for a second straight game.

When Halladay last faced the Cardinals, Lance Berkman capitalized on his lone mistake and crushed a three-run homer in the first inning. Skip Schumaker singled to lead off the second inning, and Halladay then retired 21 consecutive batters with just one ball leaving the infield. He went into robot domination mode following the longball and dissected the Cardinals lineup. Game Five will be the most important start of his career to date, which has been phenomenal but still lacks his desired World Series title.

Unfortunately for the Phillies, even typical Halladay dominance can result in a failure to advance to the Championship Series for the first time since 2007. The Phillies have been in this situation before, with an ace on the hill in the deciding NLDS contest. Back in 1981, the Phillies sent Steve Carlton to the mound with a 2-2 series tie against the Expos. Montreal tabbed Steve Rogers to pitch the final game. Rogers and Carpenter coincidentally have identical career ERA- marks — 87 and 86, respectively. Carpenter has tallied 42 WAR in his career while Rogers, who made 50 more starts, has approximately 51 to his name. They are statistically similar pitchers, which makes the comparison eery.

Rogers and the Expos shut the Phillies out, 3-0, and Carlton’s squad was gone. He pitched relatively well, but wasn’t 100 percent perfect. The fear of the Phillies fanbase is that the events of the 1981 NLDS will recur. Halladay will throw well, but it won’t be enough to overcome a tough offense that just got Matt Holliday back.

The Phillies are at home, with the best pitcher on the planet throwing, yet the majority of their fanbase will swear they are underdogs.

Regardless, the Carpenter-Halladay matchup was a long time in the making, and sentimental types will find joy in seeing two old friends who, together, could have carried the Blue Jays to their own division series, pitching against each other in an incredibly important playoff game.

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