Milledge was born in Bradenton, Florida. At the age of twelve, he pitched and played third base and hit third for the Manatee East Little League team that was the national runner-up in the 1997 Little League World Series. He received the win on the mound in the semi-final game of the regional, giving up only one run on a solo home run to Matt Rigney in a win against Mississippi.\n', 'In 2001, he led Team USA to a Gold Medal game victory over Venezuela in the International Baseball Federation\'s AA World Youth Championships. Later that year, Baseball America named Milledge the best 16-year-old player in the United States. He graduated from Lakewood Ranch High School in Bradenton, Florida in 2003 after leading his team to the state 5A title his senior year.\n', '

Prior to the 2003 amateur draft, he was expected to be among the top three selections, but as draft day approached, press reports from 2002 resurfaced regarding Milledge\'s expulsion from Northside Christian School after his junior year for allegedly having sex with a minor. He subsequently transferred to Lakewood Ranch High School where he finished his education and amateur baseball career.\n', '

As a result of the incident, Milledge was passed over in the 2003 amateur draft until the Mets selected him as the twelfth overall pick in the first round. The Mets began contract negotiations with Milledge, but the talks were interrupted in early August 2003, when the Mets learned of allegations of additional sexual misconduct against Milledge during his time at Northside. The Mets completed a private investigation of the matter and, satisfied with the results, signed Milledge to a contract with a $2.2 million signing bonus.\n', '

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