Another observation: your Jim Handiboe certainly had a remarkable career. He had an overall 404-427 mark, which is certainly noteworthy in a number of respects. Cy Young holds the record for most decisions (827), which is four less than Handiboe achieved in your game. That's quite an achievement for someone who also had a losing record.
Which got me to thinking: who is the pitcher with the most wins while still having a losing record? In other words, who is the winningest losing pitcher of all time? I'll save you the guessing - it's this guy:
That's
Jack Powell, who retired in 1912 with a 245-255 career record. He was actually pretty good early in his career, but then he got stuck with the St. Louis Browns and, in the final eight years of his 16-year career, he had only one winning season.
Why do I bring up Jack Powell? Well, because in my experience there are a lot more Jack Powells in OOTP than there are in real life. Even though, as Casey Stengal said, you have to be a good pitcher to lose 20 games in a season, it only takes a few 20-loss seasons to convince teams that maybe the guy losing all those games isn't so good after all.
Mark Maroth, the last pitcher to lose 20 games in a season, did that in 2003 and was gone from MLB by 2008.
Ball clubs typically won't stick with a pitcher who can't win on a regular basis. That's true now, and it was true in the nineteenth century as well. The second-most winningest losing pitcher in history was
Bobo Newsom, who, perhaps not coincidentally, also played for the Browns. In fact, he played for
everybody en route to a career mark of 211-222. Nobody else besides Powell and Newsom has ever won more than 200 games and ended up with a losing record.
So it would take an unprecedented combination of events to have a pitcher win over 400 games in a career and still lose more games than he won. Why, then, do losing pitchers with over 200 wins happen with some regularity in OOTP? That's a hard question to answer. Powell and Newsom played on a bunch of losing clubs, but then so did Walter Johnson, and he finished with a .599 winning percentage. Good pitchers are supposed to raise the performance of their teams.
You'd think a GM would, at some point, ask himself why he's keeping a historically mediocre pitcher on the roster when there's got to be somebody better that could take his place. That's what happens in real life, and that's what has happened throughout the history of the game. Maybe OOTP creates too many mediocre pitchers, so that there really is nobody better out there. I don't know. It's just something to think about as we admire the career of Jim Handiboe.