A deal at the 2008 trade deadline sent him from the Lions, a team that didn't make the playoffs while he was there, to the Dallas Cowboys, a team that expects to contend for Super Bowls every season.
Williams thought he was living a dream. But as his third season with the Cowboys came to an end on a wet and cold Sunday afternoon at Lincoln Financial Field, his time in Dallas might be over.
He finished Sunday's game with one catch for 6 yards and a dropped pass that he bobbled five times before the ball fell to the soggy grass. It was just another of those sad moments for Williams' season.
"I don't wonder at all," Williams said about his future. "It is what it is. I haven't played my last game in the NFL."
Williams hasn't developed a strong bond with interim head coach/offensive coordinator Jason Garrett, a strong candidate to remain as the Cowboys' full-time coach.
Williams made a comment last week that appeared to be a shot at Garrett.
"I was the go-to guy in Detroit," Williams said. "Coordinators can make who they want to make the star."
The receiver met with Garrett in the coaches office to talk about the comment.
"Out of context," Williams said of the quote and the meeting with Garrett. "If I was going to say anything I would have said it a long time ago. I'm as blunt a person and as honest a person you will ever meet. I don't cut corners, I'm going to tell you what I feel and I told him I didn't mean anything by that. It was just in general."
On top of everything else, it seemed the Cowboys were not happy with Williams' performance the previous week in Arizona, when he didn't have a single catch while playing through a groin injury. Williams said he shouldn't have been on the field and pointed that out to Garrett in their meeting last week.
This whole relationship with Williams is setting up for a divorce.
He finished the season with 37 catches, one fewer than last year, for 530 yards. He had 66 more yards and two more touchdowns in 2009.
If the Cowboys release him, it will be a roughly $12.9 million hit against the salary cap that is expected to return whenever the players and owners come to terms on a new collective bargaining agreement. The Cowboys could offer to reduce Williams' contract, but such an agreement appears unlikely.
Williams is scheduled to make $5.1 million next season, and his salaries increase until his contract ends in 2013.
But Williams might not get there. He's endorsed Garrett as the coach, but at times you hear something else, like he doesn't endorse the offense.
He started with 18 catches for 278 yards and three touchdowns in the first four weeks of the season. In the last four games in which he played, he had only five catches for 61 yards and no touchdowns.
The low numbers could be attributed to Williams, Garrett's playcalling and the types of defense out there.
Whichever it is, the Cowboys have to fix it if they keep Williams. It seems they're always fixing something with him.
It just might be time to move on for everybody's sake.
"This is my dream [to stay] here and it started out good," Williams said. "Started out real good, but it fell apart I guess you could say. I love to be here."