He needs 50 more wins to get to 400 and he's only won 3 games this year. He's 42 years old. Considering all of that it seems very unlikely.
But the reason he's winning so few games this year (his record is 3-5) is not because he's become an ineffective pitcher, in fact his ERA is a solid 3.31 which is good for 12th in the NL. It's because he's pitching for a team with an awful offense (the San Diego Padres.) It's the Padres fault that his streak of 20 consecutive seasons with 13 or more wins will likely be coming to an end this year.
If Maddux can pitch three more seasons after this one (through 2011) for a team like the Chicago Cubs (why not go back one more time?) it seems quite possible he could add 50 more wins to his career total. And it doesn't seem entirely unlikely he could pitch well to age 45 or 46 considering the high level he is pitching at now at age 42. Other pitchers have done it before him.
Some examples: Nolan Ryan 46, Roger Clemens 45, Phil Niekro 48, Tommy John 46, Charlie Hough 46, Jamie Moyer 45, Gaylord Perry 45, Jack Quinn 50, Satchel Paige 46.
Labels: Greg Maddux, San Diego Padres
The whole 2.48 ERA as a 41 year old rookie in 1948 deal is pretty incredible.
Hough's a knuckler so he could pitch for 11 bajillion years.
Perry is probably stealing people's Vaseline and rubbing it on baseballs to this day.
Moyer is probably the best comparison but he's not exactally Maddux level =/
400 is definitely a stretch, and I'd bet against, but it's not entirely impossible.