I can’t see how Zito will not lose 20 this year with how bad he’s pitching, I’m trying to think if there’s ever been a Cy Young winner who later on went on to lose 20 games in a season. I will go look it up eventually in baseball-reference, but I wonder, does anyone know this? I don’t think it’s ever happened before.
Denny McLain won the 1968 AL CYA (31-6) and co-won the 1969 AL CYA (24-9), then went 10-22 in 1971.
Steve Carlton won the 1972 NL CYA (27-10), then went 13-20 in 1973, and later won the 1977 (23-10), 1980 (24-9), and 1982 (23-11) NL CYAs.
Randy Jones went 8-22 in 1974, then won the 1976 NL CYA (22-14). Not quite the order you’re looking for.