Sure… Most trades in the NFL end up being somewhat equitable… But the trade machine in the NFL is a fickle beast—and there have been more than a few instances in which it has giveth—and subsequently taketh in a MAJOR way.
Leaving one team dramatically on the wrong side of an uneven deal.
And in a high stakes business like the NFL—all it takes is one bone-headed deal to tank a team’s chances for years to come… Something that we have seen happen plenty of times over the years.
With the offseason in full swing, we have decided to take a look back to the turn of the millennium and peg the 10 WORST trades that NFL teams have made.
Antonio Brown
Let’s start off with a semi-recent deal that blew up in spectacular fashion on the Raiders—and, really, did so in record time.
This, of course, is when the then-Oakland Raiders packaged a 2019 third and fifth-round pick to bring the Pittsburgh Steelers’ embattled star receiver, Antonio Brown into town.
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Granted, that isn’t an insane amount of draft capital to trade for a player of Brown’s caliber, but considering how spectacularly it blew up on the Raiders—it simply had to be included on this list.
Especially because upon acquiring him—the team also wrote him a new contract that paid out $50 million over three seasons—including $30 million guaranteed, which, essentially made him untradeable once the situation escalated.
Escalated how you ask?
First, it was the cryotherapy frostbite incident that got things off to a strange start…
Then. he held out of training camp because of his qualms with the league’s new helmet policy, which deprecated the Schutt Air Advantage that he’d worn since breaking into the league. This one really spiraled out of control—as the wide receiver filed a grievance with the NFL and even threatened to retire over it.
This saga caused a rift between him and the organization, particularly General Manager, Mike Mayock, who made several public comments about Brown and was integral in levying fines against Brown, which he of course posted to Instagram and angrily confronted him about during practice, going as far as to call him a cracker.
It wasn’t long until the Raiders were forced to release AB—as the distraction had gotten out of hand, meaning that for a third and fifth, all the team got was a massive headache—and the All-Pro talent never played a single game for Oakland.
Interestingly, the Raiders have been on the wrong side of a couple of deals involving high-profile wide receivers…
And this one may be even worse than the Antonio Brown story… Because they were actually on the wrong side of TWO deals involving one player.
Randy Moss
It all started when they packaged the number 7 overall pick in the ’05 draft, a seventh-rounder, and linebacker Napoleon Harris to acquire Randy Moss from the Minnesota Vikings.
Moss, like Brown, was far and away one of the most talented receivers in the league at the time, but he had fallen out of favor with the team that had drafted him.
His antics had grown tiresome and both he and the team felt they needed a change of scenery.
Unfortunately, Oakland did not prove to be the right place. Moss looked disinterested—pretty much from the start. He at least managed to top 1000 yards in year 1, though it was by the skin of his teeth, but the team struggled going four and 12.
Things deteriorated further in ’06, as the team went two and 14 and Moss put up far and away the worst season of his career to date.
The guy who had regularly put up over 1300 yards a season and double digit touchdown seasons ever since breaking into the league managed just 553 yards and three touchdowns in that horrendous 2006 campaign.
Oakland ran out of patience and sold about as low as one could on the future Hall of Famer, sending him to New England for just a fourth-round pick—and Moss proceeded to put up one of the greatest seasons of all time, snagging 98 catches for 1493 yards and a league-leading 23 touchdowns.
He’d put up over 1000 yards and double-digit touchdowns every full season he played in New England, making for one of the most epic bargains for the Patriots that the NFL has seen.
The Raiders aren’t the only team to appear on this list twice… The Denver Broncos have had two horrendous trades to speak of.
Russell Wilson
The Raiders aren’t the only team to appear on this list twice… The Denver Broncos have had two horrendous trades to speak of.
Most recently, the Russell Wilson deal.
For anyone who needs a refresher… the Broncos sent quarterback Drew Lock, tight end Noah Fant, defensive lineman Shelby Harris, two first-round picks, pick nine in the 2022 draft and their 2023 first-rounder, two second-round picks the 40th overall pick in ’22, plus the following year’s pick, and a 2022 fifth-round selection to the Seahawks for Wilson and a 2022 fourth-round pick.
And though people recognized it was a haul at the time, no one expected the ROI to be as insanely low as it now looks to be.
Because Wilson was just about as bad as you can possibly be in year 1 with Denver. He looked like an absolute shell of himself—and pretty much single-handedly kept the team out of postseason contention.
He never even really ingratiated himself with his teammates either. I suppose they weren’t too fond of his antics… Like demanding his own office at the team facilities and telling them he had an open-door policy… Yikes.
Wilson does still technically have time to turn it around, but he is going to be fighting for both his job and his legacy in 2023—and, honestly, I don’t know that he maintains either of them by the end of the season.
Tim Tebow
Denver also made the horrendous decision back in 2010 to trade three picks to Baltimore, to move up just three picks and take Tim Tebow with the 25th overall pick.
And all because their new head coach, Josh McDaniels couldn’t find a way to get along with their star quarterback, Jay Cutler, and had promptly shipped him out of town…
So—he and the rest of the powers that be decided to push their chips to the middle of the table and gamble on the lefty QB, who made his name playing more like a full-back in a college.
Granted, there were some moments earlier on when the Broncos looked vindicated—as the team did rally around Tebow for a stretch there, but Tim never really developed as a passer and both he and McDaniels were out of town in short order.
Mitch Trubisky
This isn’t the only time we’ve seen a team blunder by moving up in the draft trying to snag a franchise quarterback in the draft…
Cough, cough… I’m looking at YOU Chicago… I know the good people of the Windy City are tired of hearing about it, but how could we not include the deal that the Matt Nagy Ryan Pace brain trust made back in 2017, packaging the third overall pick in the draft, two thirds, one in ’17 and on future, and a fourth-rounder, to move up one spot to take Mitch Trubisky out of UNC.
This deal, of course, was further soured by hindsight, as Patrick Mahomes and now to a lesser degree Deshaun Watson were both on the board and taken in the first round that year… Never mind all of the valuable draft capital that the Bears blew, seemingly competing against themselves for a relatively unheralded ACC quarterback.
These are the kind of trades that can absolutely unravel an organization for years… Trubisky was simply not the guy they thought him to be…
I mean… It feels like the Bears are just now getting their footing back on solid ground again—and that took a full house cleaning to do. That’s how devastatingly bad this trade was.
RGIII
The Washington—then Redskins—pulled a similar stunt in 2012—during the infamous Andrew Luck / RGIII draft.
The two aforementioned names were the big ones looming over the draft that year… and heading into draft day—it seemed like a foregone conclusion that the Indianapolis Colts were going to take Luck first overall.
But Griffin looked to be up for grabs, as the then-St. Louis Rams were sitting at 2 and seemed more interested in shopping it than taking the former Baylor quarterback, as they still had faith in their 2010 number one overall pick, Sam Bradford.
The deal ended up being quite a haul for the Rams—they got three first-round picks, including the sixth overall pick in that year’s draft, and a second-rounder to move up to number 2, where they took the Heisman Trophy winner.
And, well, this is actually kind of a tough one to blame them for—even looking back on it…
Washington’s record jumped from a measly five and 11 in 2011 to a division-winning 10 and six during Griffin’s rookie year. And he was clearly the straw that stirred the drink.
RGIII shattered all expectations heading into the year, even outplaying Andrew Luck, a name that he’d be tied to for the remainder of his career.
In route to taking home Rookie of the Year honors, Griffin completed 65.6-percent of his passes for 3,200 yards and 20 touchdowns to just five interceptions.
That alone would’ve been a solid rookie year, but the dual-threat quarterback was so dynamic with his legs—that he nearly reinvented the position running for 815 yards and seven touchdowns.
Unfortunately, it did not prove to be sustainable… RGIII suffered that nasty leg injury—and was really never the same player. Which, really, makes this trade all the more painful for Washington.
I mean—they almost nailed it, but it still has to go down as one of the worst deals we have seen over the last two plus decades, considering the amount of draft capital they gave up—and the minimal return they ended up getting out of Griffin. Not to mention the crushing disappointment of having that temporary success!
Champ Bailey
Of course, this isn’t the only terrible trade that we have seen Washington make. Remember when they sent Champ Bailey, a generational talent at cornerback to Denver for Clinton Portis… a running back?!
The trade in question took place back in 2004, when Mike Shanahan, who coincidentally later coached Washington, was calling the shots in Denver.
Shanahan made the bold decision to trade Portis, a phenomenal running back at the time, who had accumulated over 3000 yards in his first two seasons in Denver. Perhaps he believed that Portis was a product of his running back friendly system, similar to what we’ve seen play out under his son, Kyle’s tenure in San Francisco.
Denver not only sold high on Portis in a masterful way, they truly fleeced Washington in the process, acquiring one of the best cornerbacks to ever play the game, Champ Bailey, and a second-round pick to boot!
This was an absolutely horrendous decision for Washington looking back at it… Granted, Portis did continue to put up solid numbers, but it always felt like they were empty numbers because the team never found the sustained success with him as the focal point of the offense.
Trent Richardson
At least it went better than it did for Indianapolis when they traded a first-round pick to Cleveland for Trent Richardson, one year removed from him being the third overall pick in the draft.
In Indy’s defense, Richardson had a solid rookie year in terms of traditional statistics. Just under 1000 yards and 11 touchdowns—nothing to scoff at. But he averaged just 3.6 yards an attempt and, honestly, the tapes was even more worrisome… His vision was horrendous and was lacking as a pass blocker.
All things Indy learned the hard way as he would total under 1000 yards during his 29 games there, before flaming out of the league entirely.
What a terrible way to use what would end up being the 26th overall pick in the following year’s draft.
Sam Bradford
I suppose this shouldn’t come as a huge surprise though… NFL teams love to overpay for players based on the ‘sticker value’ of their resume or pedigree… Especially if they were taken high in the draft.
The Sam Bradford trade is a perfect example of this.
Bradford was taken 1, 1 in the 2010 draft—and put up reasonable numbers during his first few seasons in St. Louis and Philadelphia. At least while he was able to stay on the field!
But he was never the franchise-altering quarterback that the Vikings hoped for when they sent a first and fourth rounder to Philly for him.
Bradford played well enough in year 1, but the team hovered around .500 with him under center, then he played just two games in 2017—before a knee injury subsequently ended his time as a Viking.
Just a horrendous return on investment Minnesota.
Willie Roaf
Last up, we have one of the worst deals on this entire list… The New Orleans Saints decision to trade Willie Roaf.
This one dates back to 2001—when New Orleans shipped their future Hall of Fame offensive tackle to Kansas City in exchange for a fourth-round pick.
Granted, he was 31 at the time, but considering he went on to make the Pro Bowl during all four seasons he played in KC—and snagged two All-Pro selections—it is safe to say that the Chiefs made out like bandits in this deal.
Meanwhile it was one of the worst trades that the Saints have ever made because even if they were entering a rebuild—they should’ve pushed for way more draft capital than a measly fourth-round pick!
An embarrassingly small haul for a player of Roaf’s caliber.
Which NFL trade do you think was the worst in the league since 2000? Did we miss anything?
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