The Cowboys gave up first- and third-round draft picks to acquire receiver Roy Williams from the Detroit Lions before the 2008 trade deadline. The Cowboys later signed him to a $54 million contract extension.

PODCAST
Fresh off retirement, Roy Williams talks about why he and Tony Romo never clicked, what he plans on doing with his time now and more. Listen

Williams never fit in with the Cowboys.

He caught just 94 passes for 1,324 yards and 13 touchdowns in 40 games in Dallas before spending last season with the Bears.

It was the worst trade in Cowboys history. Only one other can challenge it.

In 2000, the Cowboys traded two first-round picks to Seattle for wide receiver Joey Galloway. In his first game for the Cowboys, Galloway tore his ACL during a blowout loss and missed the rest of the season.

He would go on to catch 151 passes for 2,341 yards and 12 touchdowns in 48 games as a Cowboy.

Is it a wash?

No.

The Cowboys tried to make it work with Galloway as a deep threat, but it just never developed. He was a talented player, but the Cowboys were on the decline as a franchise and he was caught up in the middle of poor personnel moves.

“I’ve made a lot worse mistakes,” Cowboys owner/general manager Jerry Jones said last year about the Williams trade.

No he hasn't.

Williams has decided to retire, which revealed a little something about that trade. He was happy to play for a team in his home state. Williams is from Odessa and went to the University of Texas. His opportunity to play for the Cowboys alongside Terrell Owens opened the possibilities of great things for the Cowboys' offense.

All it did was increase then-offensive coordinator Jason Garrett’s lack of confidence in Williams’ abilities. There were times Williams wasn’t a focal point of the offense, and he was a starter. But when he suffered a rib injury while going over the middle on a pass, Miles Austin took over and caught 10 passes for 250 yards at Kansas City, including the game-winner in overtime that gave him the starting job.

Williams never recovered from a skills standpoint and couldn’t regain the starting job.

The Cowboys have made numerous trades in the franchise’s history, but Williams’ deal strikes as the worst.