I was always impressed with Steve Carlton's 27 wins for the 1972 Phillies, who only won 59 games. It was a remarkable season.
But in SOM world, I have had some terrible luck with two pitchers in the 2006 game: Brad Radke won 9 games in 38 starts with an ERA of 5.31 for my team that won 86 games. Jao Seo won 6 games in 29 starts with an ERA of 3.87 for my team that won 77 games. My bullpen was average and didn't blow too many games in either case playing at PETCO.
What is your story of futility with a Starting Pitcher?