Now, he's one of them.
"It's kind of surreal," Milledge said.
This is no typical fairy tale, however. Milledge wasn't supposed to be here; he fell to the Pirates only after two other organizations gave up on the former first-round Draft pick by the age of 24. Now, with his future in question, Milledge is in Bradenton aiming to prove the Mets, the Nationals and a host of other critics wrong.
"I've been real focused," Milledge said. "I'm just understanding what I need to do out here and the things I have to do to be successful. I'm really keeping my mind on that and staying focused on it."
The short road from Milledge's hometown of Palmetto, Fla., to Bradenton proved to be about as winding as they come. Drafted 12th overall by the Mets in 2003, Milledge breezed through the Minors, making his Major League debut less than two months after his 21st birthday. Five days later, he hit his first big league homer against the Giants at Shea Stadium, tying the game in the bottom of the 10th.
At that moment, his career hit its peak.
Heading back to the field for the top of the 11th, Milledge began high-fiving fans on his way to his position, drawing the ire of both manager Willie Randolph and the media. The Mets wound up losing the game, 7-6, in 12 innings, and Milledge -- after enduring an 0-for-13 slump and a series of poor defensive plays later that month in Boston -- soon tumbled back to Triple-A.
Milledge didn't resurface until later that year, finding himself in the middle of more controversy in late September when a teammate taped a sign reading "Know your place, Rook" to his locker in Washington. Left off the playoff roster, Milledge broke camp with the Mets the following spring, but was back in Triple-A within days.
Later that year, the Mets discovered that Milledge had helped record a rap song featuring explicit lyrics, further straining his ties with the team. A change became inevitable, and in November 2007, despite the 22-year-old Milledge's obvious power and speed potential, the Mets shipped him off to the Nationals in a deal for Ryan Church and Brian Schneider.
In Washington, Milledge received more regular playing time but did little to distinguish himself, earning nothing but another trade -- this time to the Pirates. And so Milledge and Joel Hanrahan, acquired in exchange for Nyjer Morgan and Sean Burnett, showed up to Pittsburgh last June.
With the change in scenery came a slight improvement in Milledge's numbers: a .291 average, four home runs, 20 RBIs and six stolen bases in 220 at-bats down the stretch. Then he returned home to the Bradenton area and began training for what he considers the most important season of his career.
"He realized that he needed to work," Pirates manager John Russell said. "That was the biggest thing. He taught himself as we helped teach him how to work. I think he's carried that through."
Throughout his career, managers and coaches have consistently given Milledge the benefit of the doubt, because he was always so young for his level and so remarkably gifted in so many aspects of the game.
Now, however, Milledge no longer ranks among the youngest or most promising prospects in the game. He has long since proven his ability to hit at the Major League level, but his ability to play big league defense -- and his ability to behave -- remains in question.
Yet since arriving in Pittsburgh, Milledge has established himself as a model citizen, working on his defense and otherwise staying quiet. And he is eager to prove that's no fluke.
"The main thing was my work ethic," Milledge said. "I took the game seriously, but I took it for granted, just relying on natural ability. It wasn't good enough. I could have gotten by, but I have plus tools, and I need to work and get those on display a little bit."
"I think he was on a mission," Russell said of Milledge's work since joining the Bucs. "I think he's still on a mission. I expect him to do very good things for us."
They are counting on him. Milledge will start in left field for the Pirates, in an attempt to provide them with some right-handed pop. He will use his natural gifts of speed and power to try and mold his career back into shape.
He will, in short, attempt to remain a big leaguer for the foreseeable future.
"This spring is everything coming together," Milledge said. "I feel like the most complete player I've ever been. I feel like I can be a threat on both sides of the ball. I'm excited to see what I can do."
Anthony DiComo is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.