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"Deep down I would love to play second base for the [Boston] Red Sox," the singer, 40, told PEOPLE Tuesday night in New York, while in town for the All-Star Game at Yankee Stadium.
"When I was little I wanted to be a baseball player. I wanted to be Pete Rose." Although Chesney played on his high school team, he eventually diverted his attention away toward music.
"I got into music and then I realized that I didn't want to eat, drink and sleep [baseball]," he says. "I just wanted to eat, drink and sleep."
Growing up in Knoxville, Tenn., where there is no major-league franchise, Chesney chose to became a fan of the Boston team.
"I loved watching baseball on Saturdays and they played a lot of Yankees-Red Sox games [on TV]," said Chesney, who's currently promoting MasterCard's "Roots of Rock" sweepstakes. The winner of the contest will be flown with three friends to Nashville to meet Chesney, get a tour retracing his roots in the city, and see him perform.
These days, he counts several major league ballplayers among his best friends – including Kevin Millar from the Baltimore Orioles and Nick Swisher from the Chicago White Sox – and says they have a lot in common.
"My life on tour is exactly like a baseball season. It starts in April and ends in September or the first of October," he says. "So, their off-season is my off-season, so I get to hang out [with them]."
Also being pals with other pro athletes, he notes that such friendships offer another perk: "I get free tickets."
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