Dallas Cowboys Two Worst Trades Ever: Analysis

FRISCO - Ever since the Herschel Walker trade, regardless of his role in the transaction, Jerry Jones has had a reputation as a trader. Whether that description is accurate or not can be argued.
There is one trade that stands out among the rest. Bleacher Report recently took a look at the worst trades made since 2000. The Dallas Cowboys, of course, made an appearance on that list.
Ranking at No. 4 on the list is the Dallas Cowboys trade with the Seattle Seahawks for Joey Galloway.
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Bleacher Report offered Galloway's performance while in Dallas as well as what Seattle gained in return as the reason for the ranking at No. 4:
"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.”
Interestingly enough, there can be some discussion if that was, in fact, the worst Dallas Cowboys trade since 2000.
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Fox Sports labeled the Cowboys' trade for Roy Williams in 2008 as the worst ever for the team:
"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."
Logic might dictate that with this history of trades, the Cowboys might be somewhat gun-shy about trading first-round draft picks for wide receivers.
However, the club recently gave a first-round pick in exchange for Amari Cooper. That trade, at least, seems to be working out.
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Timm Hamm has been a sports reporter and analyst since 2018 working for media outlets such as Sports Illustrated's On SI, Lindy’s Sports, Golf Central Magazine, and Fan Stream Sports. Timm hosts and produces several sports-related podcasts for the Fan Stream Sports network, covering the PGA Tour, Dallas Cowboys, Texas A&M Aggies, and Tampa Bay Buccaneers, as well as numerous other NFL teams and college programs, and is a credentialed media personality for the Big 12 and SEC. For media inquiries, please email: TimothyHamm@aol.com and follow Timm on X at @IndyCarTim