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One Cowboys trade is tabbed as among the worst of the past 20 years in the NFL

This one isn’t fun to remember.

Dallas Cowboys v Philadelphia Eagles Photo by Mitchell Layton/Getty Images

The Dallas Cowboys have been thought of as a team willing to risk a trade ever since they shipped out Herschel Walker for a boatload of Minnesota Vikings draft picks. Since that time, there has been a reputation of “Trader Jerry” in Dallas, whether warranted or not. The Walker trade is often cited as one of the best of all time if you’re looking at it from a Cowboys’ angle, and the opposite would be true from a Vikings’ angle.

But how about a trade that didn’t work out so well for Dallas? Bleacher Report recently looked at the worst trades made in the past two decades, and wouldn’t you know it, the Cowboys show up on the list. Ranking the top seven worst trades, the Cowboys come in fourth with their trade for Joey Galloway.

Through four years in the NFL, Joey Galloway averaged more than 1,000 yards per season and totaled 36 touchdowns. The wideout wanted a new contract from the Seattle Seahawks badly enough that he held out for half of the 1999 campaign.

In the following offseason, Seattle slapped the franchise tag on Galloway and engineered a massive trade win.

Galloway went to the Dallas Cowboys for a pair of first-round picks. One of those picks turned into Alabama running back Shaun Alexander, who would eventually win NFL MVP while setting a league record for single-season touchdowns. Alexander smashed Seattle’s franchise records for yards and touchdowns.

On the other hand, Galloway missed most of 2000 because of a torn left ACL. He managed 2,279 yards and 11 scores over the next three seasons before Dallas traded him to the Tampa Bay Buccaneers.

The funny thing about that is it can be disputed if that was the Cowboys worst trade in the past two decades, and the other trade that might qualify was also for a wide receiver. FOX Sports called the Cowboys trade for Roy Williams back in 2008 the worst ever for the franchise.

Back in 2008, [Jerry] Jones tried to take advantage of a terrible Detroit Lions team that was in the midst of an 0-16 season. Instead, he was the one that got the short end of a horrendous deal for the Cowboys.

Dallas sent three picks to the Lions — first-, third- and sixth-round selections — in exchange for Williams and a seventh-rounder, which they traded to the Falcons to move up in the fifth round. Needless to say, it’s a move Jones wishes he didn’t make.

“I’d love to have that trade back,” he said in 2011.

You would think that with these terrible two trades, the Cowboys would shy away from giving up first-rounders for wide receivers. But that wasn’t the case as they just recently did it again for Amari Cooper. Fortunately for Dallas that one seems to be working out just fine.

Which trade do you think was worse, the Galloway or Williams trade? The Cowboys gave up more for Galloway, but he was the more accomplished player. Some thought giving up a first-rounder for Williams was pure insanity. Neither player accomplished much once they got to Dallas.