Jennings was a highly acclaimed high school player, averaging 32.7 points and 7.4 assists as a senior, and won all major player of the year awards in his senior year. After graduating from Oak Hill Academy, he decided to play professional basketball with the Italian club Lottomatica Roma instead of playing collegiately for the University of Arizona Wildcats, leading to controversy and debate on the NBA's "prep-to-pro" policy adopted in 2006. After a year in Italy, Jennings declared for the 2009 NBA Draft and was selected as a lottery pick by the Bucks, as the tenth overall pick in the draft.
Jennings was selected tenth overall by the Milwaukee Bucks in the 2009 NBA Draft. He became the first player who skipped college to play professional basketball in Europe to be drafted by an NBA team. Jennings also made a notable appearance at the draft. He had initially decided not to attend the draft and preferred to be at a family function during the draft. After he was drafted by the Bucks, he left the family function and headed to the Madison Square Garden. He later came out on the stage after the 14th pick was announced to have his picture taken with the NBA commissioner David Stern, just like all drafted players who attend the draft.
During Jennings' NBA regular season debut on October 30, 2009 against the Philadelphia 76ers, Jennings recorded 17 points, 9 rebounds, 9 assists, and hit 2 three-point shots, just shy of a triple-double and played 34 minutes. In the second game on October 31, 2009 against the Detroit Pistons, also the debut in Bradley Center, Jennings scored 16 points during the third quarter and a team-high 24 points for the game to lead the Milwaukee Bucks to their first victory of the 2009–10 regular season.
On November 14, 2009, after a scoreless first quarter, Jennings scored 29 points in the 3rd quarter against Golden State en route to a total of 55 points in the game to break the team record for most points by a rookie, previously set by Lew Alcindor in 1970. Jennings' performance was the most points scored by a rookie since Earl "The Pearl" Monroe scored 56 in 1968. He became the youngest player to ever score 55, collecting the second-highest total for a player under 21, behind only LeBron James' 56 points in March 2005, and the second-most points scored by a Milwaukee Buck (behind Michael Redd's 57 in 2006).On February 2, 2010, he was selected to compete in the Skills Challenge.
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