Considering Milledge's track record as a disruptive force with both the Mets and the Nationals, it is a roll of the dice for Huntington and the Pirates.
"Coming out of the draft, there were many who thought he could be an All-Star," Huntington said. "In his first full season in the big leagues at (age) 23, he had a very nice year _ 24 doubles, 14 home runs, stole some bases. We think there are some things we can help him with defensively and there are some things we can help him with at the plate."
Milledge played in just 260 games over four seasons in the majors and has a career .261 batting average with 25 home runs. This season, he hit .167 in seven games _ and also blew off a team meeting and took lazy routes to fly balls _ and was demoted to Triple-A.
"There is a good person there," Huntington said. "We can help him fulfill his potential. He can be challenging at times, but there are a lot of players in baseball (like that).
"With maturity, with some guidance, with some direction, we might have ourselves a pretty good player here. It was a chance we were willing to take."
Milledge views the trade to Pittsburgh as a second - really a third chance.
I see it as a good opportunity for me," said Milledge. "I don't get caught up in what other people say about the organization and all the trades. They brought me here to try to help the ball club, and that's what I'm going to try to do."
Before arriving in Pittsburgh, Milledge played in the Pirates' Minor League system since getting traded on June 30. Most of his Minor League appearances with the Pirates came with Triple-A Indianapolis. In 17 games with the Indians, Milledge hit .333 and drove in seven runs while posting a .425 on-base average and stealing three bases.
"It's really been an experience," he said. "I've kind of had everything given to me throughout my career, being a first-rounder. This time I really had to up my game and my work habits had to get better."
Milledge had to adjust to the Pirates way of doing things.
"It was a little tough, I'll be honest," Milledge said. "Just trying to get into the swing of how to do it here in Pitt. It's a lot of discipline down there. You can't drive to the games, have to [ride on] a bus and stuff like that. I had to really get used to a lot of that stuff. It's really paying dividends."
So far Milledge has been a model citizen with the Pirates. Entering action on Sunday he was batting .230 with no home runs and six RBI.
He's been great, very attentive, very vocal with his teammates in a good way ... he's signing autographs, he's just very pleasant," Pirates manager John Russell said. "I have absolutely seen nothing other than determination and drive on the field and working hard. You hear the things from in the past, but I don't look at him and say, 'OK, I'm waiting for something to happen.' He loves being here. I think he has said it a few times in the paper, this is something that he feels like he earned."
Pittsburgh is hoping that structure and some tough love can help Milledge realize his tremendous potential.
"This guy had a pretty nice year last year at age 22 in the big leagues," Russell said. "He's been there, he's done it, and he's made some nice adjustments. He gives you a pretty legitimate bat that can do some things at the top of your order."