And when he failed to do so, it came as something of a shock to many, not least of all Milledge himself.
Milledge started as the New York Mets' great hope. This was largely based on his record in the minors, which might be characterized as borderline impressive, plus his purported "tools," which led to a first-round draft pick in 2003. But the fact was, he never produced (at a major league level) for the Mets.
He was then regarded as a talented, but lazy player, with a "when I get around to it" attitude, and was traded to the Washington Nationals, who thought so much of him that they gave the Mets outfielder Ryan Church (a better player) AND backup catcher Brian Schneider.
And perhaps part of Milledge's problem was his attitude. On the other hand, in "chicken and egg fashion," his attitude might have stemmed from a deep-seated fear that he didn't "have the goods."
The Nats suffered through a year and half of his mediocrity before trading him in disgust to the Pittsburgh Pirates. During this time, Milledge had improved his attitude to the point where he realized that he needed to earn the status of everyday player.
In accepting Milledge in trade for Nyjer Morgan, the Pirates management (positively) evaluated Milledge's newfound attitude and "maturity," meaning that they had done their due diligence. These attributes were, in fact, on display during Milledge's tenure with the Pirates.
But the underlying problem with Milledge was his basic shortage of talent.
As a Pirate, his batting average of .277 was (barely) above average. If this were true in every other category, he would have been worth keeping. But his fielding was below average, as was his power and his walk rate (which factors into on-base percentage).
At the end of the day, his talent was barely above replacement level.
One factor in the Milledge-Morgan debate was that Milledge, then 24, was five years younger than Morgan. I believe this factor is given far too much weight, and that players really need to be evaluated on a case-by-case basis.
One man may be mediocre and reach his peak at age 24 while another is a late-bloomer that is just hitting his stride at age 29—compare (older) pitcher Brian Burres to Zach Duke—Burres has more room for development.
But the tragedy is that three major league teams failed to evaluate Lastings Milledge for what he really is, a Doug Mientkiewicz-caliber role player.