A first-round draft pick out of Michigan State University, Skiles played ten seasons as a point guard in the NBA.

[1] In 1982, Skiles led Plymouth High School to the Indiana State Championship, scoring 39 points to lead the Pilgrims past the Gary Roosevelt Panthers in double overtime.

[5] Skiles attended Michigan State University, where in his senior season he was a First Team All-America selection[6] as well as the Big Ten Conference Player of the Year[7] and scoring champion.

[11] During his senior season, Skiles committed a parole violation on an earlier marijuana conviction, and served a brief jail sentence.

[1] Skiles made his NBA debut with the Bucks on November 11, 1986, against the Indiana Pacers, recording 2 rebounds and 5 assists in the 102–94 win.

[1] On June 21, 1987, Skiles was traded by the Bucks to the Indiana Pacers in exchange for a 1989 2nd round pick (which would later be used to select Gary Leonard).

[21] Despite lacking three of their top players due to injury, Skiles led PAOK to a winning record as coach in the remainder of the '96-'97 season, and an unexpected 3rd-place finish in the Greek League, thus assuring a qualification to the following year's Euroleague.

[22] Under Skiles, Phoenix compiled a .595 win-loss record and made the playoffs in two of his three years as head coach,[23] including a first-round win over the defending NBA champion San Antonio Spurs in 2000.

[25] In the first full year under his direction, Chicago limited its opposition to an NBA-best .422 field goal percentage and held their opponents to a franchise record and league high 26 straight games below 100 points.

Injuries to key players Michael Redd and Andrew Bogut marred the season, but Skiles was given a show of support by general manager John Hammond.

[citation needed] The next season Skiles had success with an improving, if still young, core led by Bogut at center and Brandon Jennings at point guard.

A midseason trades for John Salmons[29] and the pick-up of Jerry Stackhouse[30] gave Skiles both a reliable shooter and a veteran presence on the Bucks' bench.

After a gruesome injury to Bogut's right arm on April 3, 2010[31] Skiles coached his team to a decisive victory over the heavily favored Phoenix Suns.