Italian Career
On July 16, 2008, Jennings signed with Lottomatica Roma of the Italian Lega A. The contract he signed with Roma was for $1.65 million net income guaranteed and after earning the contract with Lottomatica, Under Armour gave Jennings a $2 million contract to showcase their products in the Euroleague. Jennings was the first player to play for a European team rather than play for a college basketball team since the NBA's age restriction rule was implemented.
In the Italian Lega A 2008–09 season, Jennings averaged in 27 games, 5.5 points, 1.6 rebounds, 2.2 assists, and 1.5 steals in 17.0 minutes per game. He shot 35.1 percent from the field and 20.7 percent from 3 point range in Lega A play. In 16 Euroleague games, Jennings averaged 7.6 points, 1.6 rebounds, 1.6 assists, and 1.2 steals in 19.6 minutes per game. In the Euroleague he shot 38.7 percent from the field and 26.8 percent from 3 point range.
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