Four 20 game winners in a season has only occurred twice in real life. Can it be done in WIS? I have a stacked rotation in the NWP progressive entering 1998 with Randy Johnson, Pedro Martinez, Greg Maddux, and David Wells. (Last season they won 18, 17, 16 and 15 games with limitations on IP.) These four have a real shot but with an eye towards post season play and no desire to exhaust any of these guys I doubt I can give them enough starts to get there. I added Orel Hershiser (201 ip) for depth and will watch the early going and monitor fatigue closely. If I think there's a possibility I may go for it.

Has anybody even come close here?

Yeah, a few times. It's not easy but can be done even in themes and OLs

marc, with that rotation you might get to 25 wins each! But yeah, four 20-game winners has been done:

https://www.whatifsports.com/forums/Posts.aspx?topicID=431448

I've never personally been in a league where a team had four twenty game winners, but if I got three twenty game winners with a three man rotation in an OL,for only $25 mil, I'm sure you could do it with that staff.

Just got 4 20s in the Bingo progressive 1969 season. My 115-47 Giants had Bill Singer 25-5, Blue Moon Odom 25-3, Steve Blass 23-8 and Dave Boswell 20-16.
First 3 guys got there early, but Boswell was 15-15 with 20-25 games left. So, with 4 20s as the goal, I started him every 3rd, then every other game, but was at 18 after game 159. he won one more start in game 161, then I put him in a tandemB spot for gm. 162. And he got no. 20. Happy to accomplish rare feat.

I've been unfortunate enough to be in a division where another team had four 20-game winners during my first season in the league (1981), the same four repeated as 20-game winners the next season, then three repeated again and a different pitcher joined them as the 4th in 1983. In 1984 and 1988, they had three 20-game winners plus a 19-game winner both of those seasons. I can't complain too much, though, my team did beat them in the playoffs in 1983 and 1984!

Pittsburgh Steel (derek2hof) 123-39 (1981); 115-47 (1982); 120-42 (1983); 101-62 (1984)
Dave Stieb 29-8 (1981); 22-10 (1982); 22-4 (1983); 24-9 (1984)
Ken Forsch 27-4 (1981); 20-7 (1982); 22-5 (1983)
Mario Soto 24-8 (1981); 29-6 (1982); 26-8 (1983); 22-12 (1984)
Len Barker 23-6 (1981); 25-6 (1982)
Storm Davis 24-3 (1983); 20-10 (1984)
Al Nipper 19-8 (1984)

Use high ip/g high inning SPs. By pitching deep into the games they will get more decisions, increasing their odds of winning 20.
If you build a gimmick team the best way to get 4 20-game winners is to use them at Tandem B. Set your Tandem A starters so they won't pitch 5 innings and B will poach the Wins. Rotate your 4 guys through the bullpen so nobody else gets W's late in the game. if anyone is lagging just give him more appearances. Not the most efficient way to build a team. Now the challenge is to win 80 games with that compromised team.