Standing 6 feet 6 inches (1.98 m) tall and weighing 215 pounds (98 kg), Redd spent both his collegiate and professional career at the shooting guard position.

In his rookie year, Redd was not able to contribute immediately as he was behind NBA All-Star guard Ray Allen on the depth chart.

Later on, however, it became apparent that he was better than anticipated as proven by accounts that he had played extremely well against Ray Allen, Glenn Robinson, and other teammates in practice.

[2] On February 20, 2002, against the Houston Rockets, Redd made eight three-point field goals in the fourth quarter, a then-NBA record.

In October 2002, he signed a four-year, $12 million offer sheet with the Dallas Mavericks,[2][3] but it was matched by the Bucks and he remained in Milwaukee.

[2][4][5] During the 2003–04 season, Redd's performance, amongst other reasons (ouster of Ray Allen to Seattle via a trade), was rewarded with full starter's duties and later earning averages of 21.7 points per contest en route to his first and only All-Star Game appearance.

He chose to stay with the Bucks over leaving for his home state team, the Cleveland Cavaliers, and a chance to play for less money with LeBron James.

[8] The Milwaukee Bucks were dealt a devastating blow January 25, 2009, when they learned Redd would miss the rest of the season with a torn ACL and MCL in his left knee.

[9] Redd returned for the Bucks to start the 2009–10 season, but during a game against the Los Angeles Lakers on January 10, 2010, he re-tore his ACL and MCL in the same knee that he had injured almost a year earlier.

[20][21] Redd, a devout Christian, bought a church building for his father's ministry as the first purchase after signing his contract worth $91 million over six years.

[23] Redd, via NCT Ventures, invested in Azoti, an Ohio startup that connects producers and buyers of food.