I reality, he didn't "outplay" any of his contracts until 2006, when he was awarded a sizable sum of money. He barely played in 2004, so deserved the rookie minimum, which is about how much I will make in 10 years time. In 2005, he didn't "outplay" his contract either. He played the going rate that a RT (the position he played) would make in his first full season. He showed promise, so was moved to LT and was paid generously. Even he thought so, since it was his signature on the contract. In fact, as you astutely point out, he was cut a few times and no teams even sniffed. If it wasn't for the Bills, he would have sold me the insurance I bought a month ago.
But, still, I truly sob for that 22 year-old. Many of us would kill for the tribulations he had to go through.