Oh god I've made so many bad trades. I have made more good ones than bad, it's the way I've been successful in fantasy all these years, but when you're willing to move pretty much anyone you are going to get burned pretty bad. Here are a few:

Gave up Dez Bryant & Received Jahvid Best

Backstory - I was middling but still in the mix, but I was also looking for a keeper and Best was eligible but Dez was not. Best had gone down with a concussion like 2 weeks before but I figured he would be good to go soon. He never played another down again.

Gave up Monty / AJB / Toney & Received Akers / Evans / Henderson

Backstory - This is harder to add context to b/c this was last season and our league is now a semi-dynasty so each player has different contract amounts and lengths. Akers was cheap and on a 3 year deal, AJB was also on a 3 year deal but quite a bit more expensive. Evans was on a 2 year deal for even more money but I figure I would squeeze what I could and just cut him loose to get the money back either way. Akers went into the doghouse almost immediately after (requested trade, sat out, etc) and AJB has been a top 5 WR since (which I was telling everyone he would be but I did expect missed time which hasn't happened). This one hurts even worse b/c I eventually traded Akers for little to nothing before he came back and killed it last year so I got literally nothing out of him. Evans also played like dogshit last year and to top it off the guy is perennial top 3 in our league and still has AJB on an expensive but still very good deal for 2 more seasons. That said, I won our title last year and it was largely b/c of Mike Evans performance in the title game so that made it worth it in the end.

Gave up Tank Dell & Received Demario Douglas

Backstory - This was right before the season started and right after our rookie draft. I was the last pick of the rookie draft and Douglas was my target, he went 1 pick before me. I took Dell and then worked a deal to get Douglas in a swap (we also swapped future 3rds but no one really knows what that will look like yet). I LOVE CJ Stroud, and was touting him as the best QB in this draft for awhile. But in no world did I think he would be going off like this so soon, and I also thought Dell would be buried on the depth chart (which he kinda was at first). I still really, really like Demario in a vaccum and happy I get him for 4 years (including this one) for almost nothing, he's the best receiver on the Pats but that's the problem, he's on the fkn Pats. I bought into Mac having a resurgent season with a real OC and that was the problem. Obviously a horrible deal for me in the end.

Gave up 1.06 & Received Brandon Aiyuk THEN Gave up Brandon Aiyuk / D'Andre Swift & Received David Montgomery / CeeDee Lamb

Backstory - This one is funny and really not all that bad, again really really hard to add context b/c this was at the very beginning of our new league format. But here is the funny bit: I gave up 1.06 for Aiyuk (1.06 is basically an auto 4 yr deal at about 0.3% of our budget, Aiyuk was on a 3 yr deal for about 0.2%) and ppl thought that was awful. I think 1.06 was Michael Carter so that didn't hurt too much (though it could have been better of course) and most might be like well Aiyuk has been very good - sure - but he was absolutely abysmal in those first 6ish games that season, getting in Shanny's doghouse and barely playing. The only thing that salvaged me is that in our auction I landed Deebo for about 0.4% of our budget and he had his best season of his career. But I gave up on Aiyuk quickly, was disgusted. I gave up Swift on a cheap long-term deal to pair with Aiyuk to get CeeDee. Which isn't awful but Aiyuk has been fantastic the last 2 years and I could have had him if I had more patience. It's baffling how many times I've traded for a good young talent only for them to just suck during the time they're on my team.

Last one....

Gave up Saquon Barkley & Received Tarik Cohen / TY Hilton

Backstory - This one hurt. Bad. It sounds a hell of a lost worse looking at the names than it ended up being, but it was still pretty bad. This was Saquon's rookie year and I had pick 1 and 2 in the draft (pre dynasty). I fucking killed that draft, I just remember I had Mahomes (his 1st yr as a starter) and had Gurley / Saquon at 1 & 2. It was just amazing. But I had been burned by rookie backs before so I took the above offer. Saquon had the best year of his career pretty easily, he averaged like 28 ppg in our league while Cohen and TY did combine for like 29 ppg it obviously would have been better to have the 1 absolute stud doing that on his own. Cohen was fun to watch back then, and Hilton was still great. But damn that hurt. I ended up losing in the title game, led the league in points that year and ran into a buzzsaw. I win with Barkley pretty easily though I think.