The 4 Worst Trades in Dallas Cowboys History

The 4 Worst Trades in Dallas Cowboys History
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The Cowboys weren’t scared to swing big with a trade, even if it didn’t always pay off.

I respected that about the front office when Jerry Jones was the real one in charge. I would rather the Cowboys be aggressive than be too scared to make a move.

I also want to point out that aggression and bad aggression aren’t the same thing. Dallas has made some trades that built winners. These next four trades are the ones that burned draft capital, created regret, and still bother me years later.


  1. The Joey Galloway Trade

This is the worst trade for me.

Dallas sent Seattle two first-round picks for Joey Galloway in 2000. That is a massive price to pay for any receiver, but it gets worse because I knew the Cowboys were not player away.

This wasn’t a dynasty adding one final piece. If you remember, it was an aging roster with Super Bowl stars past their prime. A fading team trying to buy speed and pretend the window was still open.

Then the worst case scenario happened.

Galloway tore his ACL in his first game with Dallas.

I can’t blame a guy for an injury. It was just bad luck, but it showed why the trade was so dangerous. When you give up two first-rounders for one player, there isn’t any cushion for it to go wrong.

If that player doesn’t become a franchise-changing weapon, the whole move looks terrible, and it did.

The pick damage made it look even uglier in my opinion.

Dallas ended the season 8-8 in 1999, so that pick ended up becoming the 19th pick in the NFL Draft. Seattle used it on Shaun Alexander.

The 2001 first-round pick ended up being the number 7 pick in the draft. The Seahawks used it on Koren Robinson after a trade down.

Dallas didn’t just lose two first-round picks. It lost one pick that became an MVP running back and another pick that landed in the top-10 of the draft.

While Joey Galloway finished his Cowboys run with 151 catches, 2,341 yards, and 12 touchdowns in four seasons, he never topped 1,000 yards in a season as a Cowboy.

I don’t like that production for two first-rounders, but who could have known?


  1. The Roy Williams Trade

I think we are starting to see a trend with the Cowboys and wide receivers, and the Roy Williams trade still makes no sense to me.

Dallas sent Detroit a first-round pick, third-round pick, and a sixth-round pick for Williams in 2008. That’s the price needed to be paid for a true WR1.

The problem is Dallas didn’t get a WR1.

Roy Williams’ best year with Dallas was 596 receiving yards and seven touchdowns. His entire Cowboys career was 94 catches, 1,324 yards, and 13 touchdowns. Talk about a let-down.

The draft slot makes this look much worse.

Dallas went 9-7 in 2008, so the first-rounder became number 20 overall. Detroit took Brandon Pettigrew,...