120 games in, all on pace for 21+ wins:

Ted Lyons 17-3
Ken Chase 17-4
Luke Hamlin 17-8
Lefty Grove 16-2
Al Milnar 16-6

Milnar? What cap?

It's a 1939 progressive, 12 teams. My team's got the highest salary at $102M. 5 other teams are in the $90M range, then 3 more in the $80M's, 2 in the $70M's, and lowest team at $66M.

Game 133: 1st pitcher reaches 20.

Al Milnar 20-6
Lefty Grove 18-2
Ken Chase 18-4
Luke Hamlin 18-8
Ted Lyons 17-4

Game 140: 2nd pitcher reaches 20.

Al Milnar 20-6
Luke Hamlin 20-8
Lefty Grove 19-2
Ted Lyons 19-4
Ken Chase 19-5

looks like about a 99.9% chance you'll make it...

Yeah. I'm kind of kicking myself now because if I had accurately assessed my team's talent level relative to the rest of the league from the start of the season, I honestly think I could have had six 20-game winners. No kidding. I've got a pitcher, Junior Thompson, with 161 RL IP who, going by ERC#, is the 3rd best pitcher of the bunch. His IP/G is only 3.63 but I could have worked around that via Advanced Pitcher Settings.

Game 141: 3rd pitcher reaches 20.

Al Milnar 20-6
Luke Hamlin 20-8
Lefty Grove 20-2
Ted Lyons 19-4
Ken Chase 19-5

Game 142: 4th pitcher reaches 20.

Al Milnar 20-6
Luke Hamlin 20-8
Lefty Grove 20-2
Ken Chase 20-5
Ted Lyons 19-4

What is your team's record at the 142 game mark?

109-34. Currently 3rd on the Top 25 list.

Game 144: 5th pitcher reaches 20.

Al Milnar 20-6
Luke Hamlin 20-8
Lefty Grove 20-2
Ken Chase 20-5
Ted Lyons 20-4

good grief. how many wins does your next highest player have?

Five. 18 games left to get him 15 wins so he can join the party!

Final update:

Luke Hamlin 26-9, 4.52
Ken Chase 23-7, 4.22
Al Milnar 22-8, 4.20
Lefty Grove 20-2, 3.28
Ted Lyons 20-4, 2.72

Chase, Hamlin, Lyons and Grove finished 1-2-3-4 in Cy Young voting. We won 123 games, and went directly to the World Series (no other playoff rounds in this 12 team league). We won four games to one, with our two-man rotation of Lyons and Grove winning two apiece and accounting for 42 of the 45 series innings.

The one game we lost was the opener, 1-0. Starting for our opponent was Bucky Walters, who had one of the greatest pitching seasons I've seen in a prog: 33-9, 2.92 ERA (if not for him, my quintet would have occupied the top five spots for Wins). He was the NL Cy Young winner, Gold Glove winner and Silver Slugger -- and he really earned that SS, it wasn't a case of "best of a bad bunch" as he put up a line of .436/.455/.622 in 178 PA.