The Biggest Trades of 2020 – a Three Year Review
“When you look back on anything in life, hindsight being 20/20, some things you’d like to have done a little differently.”
- Stone Cold Steve Austin
Welcome to the annual three-year review of Shadynasty’s biggest trades! I’m sure you’re thinking, “well what does he mean by ‘Biggest’? Does that mean most impactful? Most value exchanged? Splashiest? Most players included?”
The answer to your question is a resounding YES!
I’ve scraped through every trade from our inaugural year and carefully selected the ten trades that I would describe as BIG. This was no small task. My shortlist after my initial run through had over 25 trades I thought could be eligible. I would have loved to include them all, but lists are limited to ten so what could I do?
League reactions are actual posts on the chat after the trades. 1st round picks have the players that were taken with that pick included. Later picks are much more hit-or-miss so I didn’t bother. I determine who won each trade with full hindsight and there will be no debate and my decisions are final.
Some quick takeaways before we start:
- Less than half the league understood how valuable QBs are in a 14-team Superflex when we did the startup draft, and I suspect a few of us still didn’t understand by the time the season ended. As such, QBs are exchanged at wild prices.
- Many trades that were decried when they happened look a lot more fair today. It’s always good to explore options for maximum value, but sometimes you gotta shoot your shot. Even value+ trades can go belly up.
- No one wins every trade they make, but Darren takes so many L’s here it almost feels like I’m picking on him. I promise it’s unintentional. Keep plugging away buddy, we believe in you.
- All three of our league winners won at least one of these trades. Fortune favors the bold. Logger, Nick, Vito, Jim: stop being so pussy-ass and take some swings!
10.

Why Brent made the trade – “Antonio Gibson fast AF, no cap. Loved his athletic profile, and was in need of another solid RB to fill out my roster. Deebo and Jeudy weren’t really producing, and Kenny Golladay is a sure fire top 12 WR for years to come, right?…… Right??? I was also on a beach drunker than a bag of hammers for this trade if that’s relevant.”
Why Franzer made the trade – “Trade addiction and following hype. BTW it’s hard to look back and know why I made the decision at the time. Dynasty is a learning process.”
Why Kevin made the trade – “Mostly to get grab a 1st and try my luck with jeudy instead of golladay iirc”
League Reaction: None
Who won with hindsight – This trade flew under the radar, I think, because it was a bunch of similarly valued players getting shuffled around. Half of these guys have tanked in value at this point, which gives us a clear winner for this trade. Getting rid of Golladay, Mims, and Lindsey at the peak of their values? Probably luck more than anything but still. My Ruling: Kevin.
9:

Why Darren made the trade – “I’m not saying it was the aliens. But it was the aliens.”
Why Jerry made the trade – “At that time I was tanking and I believe Darren didn’t have a starting QB. For his superflex.”
League’s Reaction – “Is this real life?”
Who won with hindsight – Our first example of wonky QB valuation. It will not be the last. Drew Brees would retire after this season, but not before putting up his worst fantasy numbers of the past decade. A low-key disaster of a trade. My ruling: Jerry.
8:

Why Franzer made the trade – “I believe it was due to Hooper coming off a strong season in ATL and getting PAID by CLE. ‘Follow the money’. A prospective Hooper and two firsts seemed like pretty good value at the time for an injury risk in Kittle.”
Why Brandon made the trade – “Kittle was #2 TE in fantasy. I had too many Browns players. And Hooper sucked. Also noob to dynasty.”
League Reaction – “Poor Austin Hooper…” “Oh shit I almost forgot: RA*E”
Who won with hindsight – I think most of us would say that was fair value for a stud TE at the time. But man does it look lopsided with hindsight, especially when you see that one of the picks turned into Jamar Chase. Kittle would get injured for the stretch run that year and has been good-not-great since. I also love the extra $10 faab thrown in as well, as if that was enough to push it over the edge. My Ruling: Franzer
7:

Why Brent made the trade – “I didn’t see my team as ‘win now’ immediately after the startup, and no one else was tanking. I thought a move like this would net me 3 young pieces to build around later. Loved Scary Terry’s upside and Jerry Jeudy as a prospect.
Why Caleb made the trade – “Let me be Frank. I’m a trash manager, ‘The Trashman’, if you will. I had no idea what I was doing being in a dynasty league for the first time. In order to hide my lack of knowledge, I went for the win now strategy (fail) and traded for the best WR in the league. I also had confidence in a recently drafted Chase Claypool who ended up having a great rookie year. Looking back now, that trade highlights my lack of knowledge rather than hiding it….how poetic.”
League Reaction – “100% FLEEEEEEEECED 100% polyester/rayon blend FLEECE” “Wow.” “Wow.” “Wow.” “If you ain’t first you’re last.”
Who won with hindsight – This one is complicated. On the one hand, Brent would win the title this season while getting younger and more diversified. Caleb hasn’t finished top 3 in three years. On the other, Adams has finished as WR1, 2, and 3 the past three seasons. Brent’s three WRs have one top 10 finish between them. In other words, Brent won the title and Caleb floundered, both despite this trade. My Ruling: Even.
6.

Why Fuzz made the trade – “I had taken two young workhorse RBs with my first two picks, so obviously I needed to round out my roster with a high end WR as well. I was targeting OBJ but settled on Juju. I came out of that draft with Darnold and Danny Dimes as my starting QBs. Mistakes were made.”
Why Siegrist made the trade – “With the power of hindsight, it was a huge fucking gamble that worked out for me. I had just drafted AJ Brown at 2.14 after his rookie year and was on the clock for 3.1 when (Fuzz) DMd me if I was open to trading. I was thinking that I really needed a QB seeing as it was a superflex league and hadn’t drafted one, but it seemed only brnt and jry had caught on to the value of QB so I decided to push my luck to see if I could get Kyler at 3.13 and get an extra decently high pick. Kyler went 3.12 to brnt, I raged.”
League reaction – “Wow things are already getting crazy up in here.”
Who won with hindsight – Shadynasty’s first official trade! Shame it turned out to be so lopsided, even with Dak being injured for 17 games in the last three years. Juju never got back to his rookie season production, and QB is king in Superflex. My ruling: Siegrist.
5:

Why Fuzz made the trade – “With Darnold, Dimes, and Rivers as my QBs, the value of a high end quarterback in Superflex was becoming clear to me. Cam Newton felt like an attainable asset given Brent’s already strong QB room, and I wanted him thanks to brnt talking him up so much. Never again. Also, adding Taylor and Squirt’s 1.02 was an idea that came to me in a dream. And dudes think Zer has a trade addiction.”
Why Brent made the trade – “Similar thought process here, although I think this was the point I was beginning to realize my team was actually pretty good. I was able to secure a top young RB + a productive vet WR with some draft capital and an old QB that was sitting on my bench.”
Why Jerry made the trade – “I think that was still the tank situation and I needed to get the presumed #1 pick (Fuzz) had gotten from Squirt. I went from trying to compete, to tanking, to not tanking in like 3 weeks time frame.”
League Reaction – “BOOM. 3 WAY TRADE. WOW, WHAT A STORY.” “Damn fuzz giving up squirt first”
Who won with hindsight – The league’s first three teamer! In hindsight, that should not have been a reason to do it. This trade is drunk. Taylor broke out shortly after this and helped carry Brent to a title. My Ruling – Brent.
4:

Why Fuzz made the trade – “My three week Cam Newton experiment exploded in my face, so I decided to shift gears into tank mode by moving Nuk. I jumped on Josh Allen having a bad week amidst a breakout season to snag him and a former 1st round TE in Fant. And just like that, my sins were washed clean.”
Why Darren made the trade – “Probably because I wanted to.”
League Reaction: None.
Who won with hindsight – If we weren’t sure about Allen as an elite QB when this trade happened, all doubts were erased before the season ended. Allen finished as QB1, 1, and 2 the past three years, and was a large reason the Wimps won a title in 2021. Giving up a top 5 dynasty WR for a consensus bust QB was a bold move that paid off. My Ruling: Fuzz.
3:

Why Darren made the trade – “Idk.”
Why Jerry made the trade – “I needed a high end RB at the time to try and compete and thought Darren needed additional starting caliber players. Think Gordon and gurley were both top 15 rbs at the time and addition of a potential starting QB might be enticing.”
League Reaction – “So we’re gonna complain about Carson for Lindsay and a 3rd, but totally ignore the fact that jerry traded a 4th string QB and some washed RBs for the best back in the league?” “Darren got useful assets.”
Who won with hindsight – A classic four quarters for a dollar trade. Jerry has been the big dog of this league for 2.5 years and this trade was like Thanos adding the Mind stone to the Infinity Gauntlet. Hindsight makes this trade look worse than it was, as Love still hasn’t turned into a playable asset and both Gurley and Gordon ran out of gas quickly. Sorry Darren, you’re 0/3 in big swings. My Ruling: Jerry.
2:

Why Fuzz made the trade – “I took the 1.01 in the startup because I thought it was good value, even though I wasn’t big on Burrow. I assumed Squirt would be hot for him and I was right. I also assumed he would be undervaluing his 1st the next year and was right about too.”
Why Squirt made the trade – “Cause Joe Fucking Burrow.”
League reaction – “That is not a low price.” “It hurt to accept that. I feel like an accomplice.” “This was obviously a lopsided trade, but Squirt also has a glaring need at QB.”
Who won with hindsight – This trade almost destroyed Shadynastys before it even started and led to a lengthy debate on vetoing powers. It was a huge risk by Squirt to give up so much for a rookie who the Bengals hadn’t even drafted at that point, but sometimes it pays to get your guys. Odell fell off a cliff immediately, while Fields and Swift have both failed to live up to expectations despite retaining most of their value. Burrow, however, looks like The Man and led Squirt to his first title game appearance this past year. My ruling: EVEN.
1:

Why Franzer made the trade – “Seen the writing on the wall and did not think I could compete at the time or near future so I decided to blow it up for shits and giggles. No point in being stuck in the middle.”
Why Squirt made the trade – “Cause I wanted picks and to clean house I guess. I did not see much value in Gordon.”
Why Jerry made the trade – “Zer said he was looking to tank and I didn’t think I could out tank him.”
League Reaction – “Jesus Christ.” “So zer tanks for a guy with douchey long hair….who will suck…and a ohio state qb who always suck in NFL…while Jerry over here play 4d chess.” “Remember when squirt traded up for the 1.01, and that led to a league-wide discussion on vetoing horrible trades?? This one is so much worse.”
Who won with hindsight – The Behemoth. Where to even begin? There has not been a bigger shift of power before or since. I can’t even imagine what the discussions leading up to this looked like. Jerry turned his tanking squad into a leading contender with a snap of his fingers. Zer went all in on Trevor Lawrence and the 2021 draft. Squirt got younger and much more diversified without giving up much of anything.
So who won this trade? I think all three guys could make a strong case. Jerry has been collecting checks from the rest of the league the past two years and has only recently shown signs of slowing down. Still, no title yet, and only three of the players he traded his five 1sts for are still relevant. Zer is set up well for the next five years (if he can stay out of his own way). But zero playoff appearances in three years is hardly a “win.” And he traded his golden boi Lawrence as well, the impetus for this entire trade. (That one should be a fun review in two years.) That’s why I think I’m leaning Squirt here. I love a pure value gain trade, and turning those three older players into all of that young value gives me a big rubbery one. My Ruling: Squirt!