He was originally drafted as a second baseman by the Detroit Tigers in the 33rd round of the amateur draft. In 1973, he played for the Anderson Tigers, posting a batting average of .246 with one home run and 26 runs batted in in 86 games, drawing a lot of walks. With the Clinton Pilots in 1974, he batted .229 with one home run and 25 RBI in 110 games, with a .932 fielding percentage.

From 1978-1985, Wolff coached the baseball team at Mercy College.

Wolff found himself on the Cleveland Indians coaching staff from 1990 to 1994, where he dealt with baseball psychology.

After his baseball career, he became a writer, among other things.

Writing an article for Sports Illustrated about the minor leagues, Wolff got the chance to fill in for Cesar Bernhardt of the South Bend White Sox for a three-game series against the Burlington Braves during the season. He went 4 for 7 at the plate, driving in three runs and hitting a double. His average-.571-was the highest among all players in the Chicago White Sox chain that year. Because he played for three games during the season, he also got a championship ring when the South Bend White Sox got to the playoffs.

Wolff is considered an authority on children's sports and sports psychology, and he is the chairman of the Center for Sports Parenting. He has also hosted The Sports Edge on WFAN Radio in New York City. In 1997, he co-hosted a videotape program called Youth Sports with quarterback Steve Young.

Wolff is currently a consultant to the Peekskill Robins, a team in the Atlantic Collegiate Baseball League.