As dynasty fantasy football managers, it’s important to regularly assess our rosters. We need to know whether we’re in a contending window, hovering around the middle of the pack, or facing a complete rebuild. If you can manage to be objective and honest about the state of your squad, then you should be able to figure out where you stand. If you are truly a contender, then it’s time to make sure you are running out in front of the pack.
The offseason is the perfect time to look for players at a cheaper cost than you can grab them in-season. If you wait until when you really need depth or elite play, you could handicap your team’s future for the sake of a ‘ship.
With this in mind, I’ve been making some moves. To be completely honest, I have invested a ton to secure top-tier talent in the process. But a bet on the present doesn’t always have to set you up for a future dynasty rebuild. Instead, if you can insulate your build properly and still retain tradable assets, you can win today and tomorrow.
So let’s have a look at three deals I’ve made recently and how the flip can help me earn the chip.
The Upgrade to Contender Status
The first deal I’ll discuss here is a quarterback upgrade.
I finished third in the regular season a year ago in this league. But I was bounced in the first round with some insanely poor play from my guys. Most notably, Russell Wilson was out for his week 15 matchup against the inept Cardinals. Matt Ryan and Taylor Heinicke were also predictably bad.
Given those names I just dropped, I clearly needed to make a move for a legit QB. Especially in a superflex league, going into the season with Wilson and the duo of Heinicke and Desmond Ridder was not a winning strategy. So, I made this move about a month ago:
On the surface, I gave up a ton here. I still believe Kenneth Walker sees the lion’s share of the work in the Seattle backfield this season. I also mortgaged my future by surrendering two 1st round picks. However, I got a top-six dynasty QB in Lamar Jackson while replacing Walker with Miles Sanders. I think Sanders gets the bulk of the work for the Carolina Panthers for the next two years, and his contract seems to support this take. But I did give up 4 years of running back age in the process. This is a classic overpay, though not too egregious.
But I’m overpaying for a chance to win my dynasty fantasy football league this year. As you’ll see with my upcoming examples, it’s also a strategy I’m okay with provided the value is there. In this case, I’m going all in with this roster in a 12 team league.
There are some question marks here since the deal has been done. Saquon Barkley may hold out while Joe Mixon could be suspended or just flat-out released. Darren Waller has dealt with injuries over his past two seasons and my flex spots aren’t strong. But what is clear is that my wideouts and top three RBs are poised to help me win now. And with Jackson pushing Wilson to QB2, this lineup is looking a lot better than it did a year ago.
My bench is less than ideal, with Ridder, JuJu Smith-Schuster, and Wan’Dale Robinson as my best assets. But I do have some upside in Puka Nacua, Nathanial “Tank” Dell, Gerald Everett, and Tim Patrick. I even have Ridder’s and Waller’s backups to insulate against injury. It’s a contender for sure, even if on the weaker side.
This deal, though robbing me of two first-round picks, was a no-brainer. Buying a massive upgrade at QB for a team that should compete yet again made too much sense. And, I’m not just selling out for the short term. While Sanders’ window is likely small, Jackson should be a QB1 for a long time. This squad probably has a two-year window of competitiveness anyway, so at that point, I’ll either go all in or tear it down to the studs in a rebuild. Hopefully, though, I’ll have a championship trophy or two to show for it.
The Massive Overpay for a Young, Contending Core
Dynasty rosters come in many flavors. So do overpay trades. And when I tell you that this is the most I’ve ever extended myself to get a deal done, you’ll believe it… especially when you see this:
I made this move a month ago and, now that I’ve had time to sit with it, I’m still okay with the deal. Sure, Terry McLaurin could continue his high-end WR2 ways. Jonathan Mingo could become a target hog in a wide-open Panthers’ wide receiver room. Cole Turner has a path to becoming the Commanders’ TE1 this season. And, of course, the two first round picks, popping up in this deal, too.
It’s a ton to hand over. But, if I’m going to spend big, I’m going to get a young stud wide receiver for my trouble.
Chris Olave was the PPR WR25 last season as a rookie, amassing 119 targets and turning them into over 1000 yards receiving. He clearly had the second-best season of any rookie wideout, and he rivaled the numbers of college teammate and consensus rookie WR1 Garrett Wilson. In short, Olave was a stud last season. And if you’re going after a young, productive wide receiver in dynasty, you should expect to pay up.
But this move isn’t just about present contention, though it is. It’s also about solidifying my core for the future. And my core is my corps – specifically, it’s my wide receiver corps – and even in a 10 team league, it’s nothing short of magnificent.
Justin Jefferson, CeeDee Lamb, and Tee Higgins are three of the younger, established, super-productive wideouts in dynasty fantasy football. While Higgins has Ja’Marr Chase in front of him, he’s still a part of a prolific pass offense, finishing as last year’s PPR WR18. With the aforementioned Wilson on this squad and now Olave, I have an incredibly young and star-studded core at WR and RB.
Now, securing Darren Waller in this move was no mere afterthought. In fact, Waller was my initial target. But when the price was higher than I was willing to pay, moving for the elite TE and Olave was my play. Upgrading over David Njoku was a major boon for this team, and I expect Waller to be the number one option in the Giants’ passing game this season. It should be wheels up for this squad this season, after finishing in the middle of the pack last season.
But just one more quick note about the massive overpay here. Though I am not without my next two firsts, I’m okay with it. None of my top-five wide receivers is over the age of 24. In fact, only quarterback Kirk Cousins and Waller are starters over the age of 26. And with Matthew Stafford, Ridder, Alexander Mattison, Njoku, and a mix of upside and youth on my bench, I don’t really need the late firsts much anyway. And, if I fall off quickly, I can always cash in those youthful productive wideouts and build it over again.
The Over-the-Top Move to Contend Now in Dynasty Fantasy Football
The final trade I’m going to look at again involves me sending away a 2024 first round pick. However, this time, I sent my ‘24 second instead of a 2025 first rounder. Still, it’s not necessarily an overpay, but a more traditional pay-up for a productive veteran dynasty move.
While I didn’t lose much in Rashid Shaheed in my opinion, I am paying for a guy who just proclaimed his retirement two years early. Tyreek Hill is one of the best currently doing it, but I’m paying for a short window if his statements this offseason are to be believed.
But, typically, these are the type of moves we should look to make as contenders. Which guys put me over the top? Do I really need to hold on so tightly to later, future first-round picks? Can I buy just one championship a la the NFL’s Rams that will make all of this effort worth it? For my money (and draft picks), the answer is most decidedly “yes”.
The first thing to understand about this deal is that I was moving to solidify both the depth and upside of a squad that lost in the championship last season. My Kirk Cousins and Justin Jefferson stack killed me in week 17 last year, netting just a combined 9.4 points and nuked my chances. JJ cost me three ‘ships last year. I’m still not over it. But now that Hill has been added to the fold, I’m able to move my new WR3 in and, hopefully, profit from this lineup.
The Cousins/Jefferson/TJ Hockenson and Joe Burrow/Chase stacks are a chef’s kiss, while Tony Pollard, Sanders, Olave, and Chris Godwin round out an elite starting roster. The bench is light, but Allen Lazard, Tim Patrick, AJ Dillon, and three Giants receivers should be enough. Of course, nuking my chances at acquiring the necessary depth in-season was not ideal. However, the chance to insert Hill into this corps on this team was too good to pass up.
I’m a big fan of making a move for one elite guy to put my dynasty roster over-the-top. It’s a power move that not only makes other contenders uneasy but puts them on notice. This should naturally spawn other deals and, if you’re lucky, maybe some panicked mistakes in the process. Though the ultimate goal is improving your team, it’s also an added bonus to stick it to your leaguemates. After all, what’s dynasty fantasy football if we’re not having fun destroying our friends’ hopes and dreams?
Dynasty Fantasy Football Trading Conclusion
It’s important for me to note that I’m not overpaying just for the sake of it. All three of these deals were legitimate trade discussions that went back and forth multiple times. The overpays here were carefully considered and meticulously negotiated, ensuring it was worth it on my end.
In dynasty fantasy football, I’m not looking to win every trade. I’m looking to win nearly every trade, but the end goal should be to make your team better. If, at the end of the day, you’ve done that for both the long and short term, consider the deal you made a winner. And, as a contender, seal the deal by grabbing elite contributors who fill your roster holes and elevate your squad beyond the others. When you find yourself in that contending window, step on the throats of your opponents and do what you must to ensure the ‘ship.
Jeremy Shulman
Jeremy is an avid football fan from New York who lives in Amsterdam and roots for the Patriots. This walking contradiction has played fantasy football for over than 20 years. He is now a Senior Dynasty Writer at The League Winners. In his spare time, he writes and edits professionally.