Pole made his major league debut on August 3, 1973, starting the second game of a doubleheader against the Baltimore Orioles. He surrendered six runs in 3 2/3 innings pitched and received the loss, as the Orioles won 8-2. He remained with the team, and spent the next four seasons moving between the rotation and the bullpen for the Red Sox.
Pole's career was nearly ended by an injury during a game against the Orioles on June 30, 1975, when a line drive by Tony Muser struck him in the face. The ball had been hit so hard that it bounced into foul territory near third base, scoring two runs on the play. Pole sustained a broken jaw and damage to the retina of his right eye. The damaged eye never fully recovered, and he ultimately lost 90 percent of the vision in that eye. Pole recovered from his injuries in time to pitch in the 1975 World Series, walking the only two batters he faced in a 6-2 loss to the Cincinnati Reds in Game 5. The Red Sox ultimately lost the series in seven games.
At the end of the 1976 season, Pole became one of the inaugural members of the Seattle Mariners franchise, as they selected him from the Red Sox with the seventh pick in the 1976 expansion draft. Pole spent 1977 and 1978 with the Mariners, but his performance was not up to the standard he had set in Boston, possibly due to effects from the injury. His most memorable moment with Seattle came on August 5, 1977, when he surrendered Reggie Jackson's 300th career home run.On March 24, 1979, Pole was released.
Pole ended his time in the majors with 25 wins, 37 losses, one save, and a 5.05 ERA in 122 games pitched and 531 innings. After the end of his major league career, he continued to play professionally in Mexico.
Maddux credits Pole as a major influence, and a significant contributor to his success. In a 2005 interview, he said, "I remember when Dick Pole told me one day, ‘Why don’t you stop trying to strike guys out? Just try to get them out, and you’ll probably strike out just as many guys, if not more. He was right. I’ve always tried with two strikes just to make a pitch and get the guy out. You get a lot of strikeouts just on accident.
Pole returned to his roots as pitching coach for the Pawtucket Red Sox in 1992, then spent 1993-1997 on the coaching staff of the San Francisco Giants, under Dusty Baker. Pole next worked as bullpen coach for Boston in 1998. After that, he was pitching coach for the Anaheim Angels in 1999, for the Cleveland Indians from 2000-2001, and for the Montreal Expos in 2002. He re-joined the coaching staff of the Cubs in 2003. He is currently the pitching coach for the Cincinnati Reds, taking the job in early November 2006.
Pole's name is often treated in humorous fashion by sports columnists and pundits because both his first and last names could be considered euphemisms for "Penis