Dynasty Fantasy Football Trades Gone Bad: Dak Prescott For Who?

Hi, my name is Jake and sometimes I make bad trades.

Look, I’m not perfect. I’m not batting 1,000 in the ol’ trade market. I have, on occasion, made some breathtakingly awful transactions, especially early in my dynasty career.

I once traded away Dak Prescott for Josh Rosen plus a couple of meaningless rookie picks. In a Superflex league. Yes, Joshua Ballinger Lippincott Rosen, a first-round draft pick by the Cardinals who was replaced a year later by Kyler Murray. I did that willingly. I wasn’t being blackmailed. No one had taken my dog hostage.

So believe me when I say I understand the anguish someone can feel looking back at a horrible, no-good, very bad dynasty trade.

That’s why, today, I’d like to help you move on. To cleanse your dynasty aura before the NFL season begins anew. To do that, we must first confront our past sources of angst and negativity …

Confessions Dynasty Fantasy Football Trades Gone Wrong

I enlisted some help from my followers over on Bluesky. I asked them to bear their souls and share the worst dynasty trades they’ve ever made.

And folks, I heard some stories.

I heard tales of future studs traded away for pennies. Of former studs acquired and then promptly disintegrating. I even encountered the name Laquon Treadwell. Talk about a jump scare!

Out of respect for their anonymity I’ll withhold the names of those who were vulnerable enough to share their dynasty trauma with me. But I do want to share their stories. To look these rough decisions in the face and maybe even try to learn something from them.

Deep breath in. Deep breath out. OK, let’s do this.

Matthew Berry's Draft Day Manifesto

Confronting the Ghosts of Dynasty Past

I don’t blame you for mentally blocking out some of the details of this trade. That’s often our brain’s way of trying to protect us.

Losing Brock Purdy for such a pittance obviously stinks. But it’s the fact that you had the choice between Purdy and Kenny Pickett that really rubs that salt into the wound. Then again, when faced with choosing between a first-round draft pick–even a tiny-handed fella like Pickett–and the guy chosen with the very last pick of the draft who was almost definitely going to get leapfrogged by Trey Lance … I get it.

Lesson: Draft capital usually matters! Right up until it doesn’t.

It’s unfathomable now to think of Derrick Henry as anything but “The King” of fantasy football, but there was a time when Henry looked like a complete bust.

His rookie year, he was firmly stuck behind another legend, DeMarco Murray. The next year he was stuck splitting time. When Murray was finally out of the picture in 2018, Henry averaged less than 40 rushing yards per game through the first 13 weeks!

And then, without warning, Henry busted out a 238-yard, 4-touchdown rushing performance. WHO THE HELL COULD’VE SEEN THAT COMING?? You gave the guy plenty of runway to prove himself and it’s not your fault that it took two-and-a-half years to finally take off.

Lesson: It’s pretty clear. Never trust Rob Gronkowski.

Matthew Berry's Fantasy Football Rankings

As poorly as that first trade turned out, it still warms my heart to see the name Tyler Boyd. I fondly remember those couple of years as the Bengals default WR1 and you can never take that away from us.

Not all rookie draft picks are created equally. The vague idea of getting three first-round picks for a couple of stud players sounds reasonable enough on the surface. But how sure are you that they’ll be early-round picks? And even if they are, can you be certain you'll land a future star with them?

Lesson: A stud in hand is worth three in the bush.

Is this … is this a warning not to abandon Chris Olave? Because it sure feels like a warning not to abandon Chris Olave, who just signed a big ol’ contract.

I think the timeline in this post is slightly off (Jameson Williams wasn’t drafted by the Lions until 2022), but the point remains. An exciting wide receiver prospect joins a team with a well-rounded WR1 and the impulse is naturally to downgrade the veteran and hype up the rookie.

Lesson: Sometimes a really good receiver is just … a really good receiver, and can earn targets at a high level regardless of some added competition.

GAHHH, sorry about that. This image should’ve been preceded by a trigger warning.

When Treadwell entered the league as a first-round pick, Davante Adams was really bumming out Green Bay fans and dynasty managers alike. He hadn’t topped 500 yards in a season. He was dropping EVERYTHING. There was a chance he’d never live up to the hole left behind by Jordy Nelson.

So you did what you felt you had to do. And he made you pay.

Lesson: Leave Matthew Golden alone! He’ll be fine!

To be honest, I’ve been waiting a long time for Chase Brown to be supplanted in that Bengals backfield. Where are my Tahj Brooks believers at? But I’m finally ready to admit that he’s the guy … just in time for his fantasy football ADP to be at an all-time high.

But hey, if you buy into Jaylen Waddle leading the Broncos depth chart (and I do), his value may be inching back closer to Brown’s. Still a bummer, but not such a catastrophe as this first seemed.

Lesson: On a long enough timeline, even the bad trades can look decent again.

Don’t Let Your Past Dynasty Trades Dictate Your Future Dynasty Trades

If you leave this article with only one takeaway, let it be that Laquon Treadwell owes everyone who drafted him a dollar.

If you leave with TWO takeaways, the second should be that one bad trade does not define you as a dynasty manager. It’s what you do AFTER that bad trade that counts.

Now that you’ve borne witness to these other managers’ shame, I invite you to look inside yourself. I want you to think about one of your own bad dynasty trades. Conjure up every grim and embarrassing detail. What’s one thing you can learn from it?

And now close your eyes and picture driving away from it, staring at it in the rearview mirror until it fades away completely into the horizon. There. It’s gone. It can’t hurt you anymore. And you’re going to keep driving, looking forward to that long dynasty road ahead of you.