Maddox began his career with the San Francisco Giants but, rose to prominence with the Philadelphia Phillies where his impressive defensive play earned him eight consecutive Gold Glove Awards and, where he was a member of the 1980 World Series winning team.

[4] While playing with the Giants' minor league affiliates in Salt Lake City and Fresno, California, Maddox discovered that other Giants minor league rookies received higher bonuses and were paid more per month, so he requested that the team's front office staff place him on the same level.

"[a] In 1976, Maddox had his best year as a hitter, with a .330 batting average, and helped the Phillies win the National League East, their first postseason berth since the Whiz Kids in the 1950 World Series.

But the team lost three consecutive National League Championship Series, including in 1978 against the Los Angeles Dodgers as Maddox made a crucial error in Game Four.

With the score tied in the bottom of the tenth inning, two out, and Ron Cey on first, Maddox misplayed Dusty Baker's fly ball.

In the 10th inning of the fifth and final game of the 1980 NLCS against the Houston Astros, his double scored Del Unser for the pennant-winning run.

In the bottom half, he caught Enos Cabell's fly ball for the final out to put the Phillies in the World Series for the first time since 1950.

During his career, Maddox played in six postseasons, winning five full-season Division titles, two pennants and one World Series, all with the Phillies.

But he did hit 337 doubles and 62 triples, products of the speed that also allowed him to run down fly balls few outfielders could reach, and to steal 20 or more bases in nine straight seasons.

After retiring, he founded World Wide Concessions, a leading national promotional products company specializing in unique branded gifts and packaging.

[17] On December 16, 2010, the Gaming Control Board voted to revoke the casino's license after the venture failed to secure funding.