He went 15–6 with a 4.04 ERA his only season in the Reds' farm system, after which he and Woodie Fryman were traded to the Chicago Cubs for Bill Bonham.

He earned his first major league save on September 28 against the Pittsburgh Pirates[4] and was second only to Dick Tidrow with 72 games pitched for the Cubs.

On April 1, 1982, Caudill was one of two players to be named later from a 1981 mid-season deal in which the Cubs received Pat Tabler from the New York Yankees.

The Yankees immediately sent Caudill, Gene Nelson, and a player to be named later to the Seattle Mariners for Shane Rawley.

[6] On another occasion, when brought in to pitch in a one-sided game, Caudill appeared from the bullpen sporting a half-shaved beard.

On November 21, 1983, Caudill and Darrel Akerfelds were dealt to the Oakland Athletics for Dave Beard and Bob Kearney.

With the NL leading 2–1, Caudill was brought in to pitch the seventh inning, and he struck out all three batters he faced, Tim Raines, Ryne Sandberg, and Keith Hernandez.

Oakland traded Caudill to the Toronto Blue Jays on December 8, 1984 for Dave Collins and Alfredo Griffin.

[1] Caudill was manager Bobby Cox's top closer upon his arrival in Toronto, but lost his job to Tom Henke by the end of the 1985 season.

However, after just a month with the A's, he suffered a broken hand after punching a man who was reportedly trying to accost his wife in a hotel parking lot in 1987.