How To Win Dynasty Fantasy Football: Expert Tips and Tricks For A First-Time Player
Matthew Freedman runs through his favorite tips and tricks to get you thinking in the right mindset for a successful dynasty fantasy football career.
There are a lot of great fantasy football formats out there.
Season-long redraft. Best ball. Guillotine Leagues.
They're all fantastic.
But my personal favorite is probably still dynasty, in part because I like the long-term nature of it. In redraft, best ball, and Guillotine Leagues, if you take a drastic stance on a player and you're right, your boldness benefits you for just one season.
But in dynasty, if you're right on a player in a big way, you receive the dividends from that decision forever … or at least as long as the league exists.
I like that idea.
Have you never played dynasty, but you want to get into it?
Great.
This piece is for you.
Here are five big-picture items and a couple of specific strategies to keep in mind as you begin your very own dynasty adventure.
For more dynasty fantasy football strategy, picks, and more, subscribe to the free Fantasy Life Newsletter—where every Saturday is dedicated to dynasty deep dives.
Premium
Go FantasyLife+
Your league is unique. Your advice should be too. Get personalized tools, rankings, and projections tailored to your fantasy football league settings.
Expert Tips on Winning A Dynasty Fantasy Football League
Know Yourself
In Hamlet, Polonius gives his son, Laertes, this counsel: “To thine own self be true.”
Unfortunately, Polonius is a tedious moron who dies because of his meddling stupidity, and Laertes is an unthinking puppet whose illogical puerility brings about the play's bloody end.
Still, I guess "to thine own self be true" is decent advice.
And to be true to yourself, you must first know yourself.
What do you care about more?
- Competing every year
- Winning a championship
Every fantasy manager wants to win a championship ultimately, but what do you care about most: Consistently having a good team, or winning it all?
Maybe phrased differently: Do you care more about process? Or results? The journey? Or the destination?
Think 10 years into the future. Which outcome would you rather have?
- One random championship and nine seasons out of the playoffs
- 10 years in the playoffs, five seasons in the championship game … but no title
When your dynasty league ends, do you want to be able to say that you won a championship? Or do you want to be able to say that you competed every year and had one of the league's best all-time franchises?
There's no wrong answer.
You just need to determine what your goal is—and then craft your approach to that goal.
Know Your Timeframe
Once you know yourself and your goals, then you can determine your optimal operational timeframe.
If you simply want to be a champion at some point, then you can afford to be shortsighted and go all-in when you want to attempt to maximize your odds of winning a title in any given season.
That would mean trading young players and future picks for current stars and contributors who can help you make a championship push.
Essentially, you're Rams GM Les Snead, and your mantra is “F*ck them picks.”
You're Reese Bobby: “If you ain't first, you're last.”
Napoleon: “Who retreats?”
If your goal is to win a dynasty championship or die trying, you can be reckless. In a worst-case scenario, you'll inadvertently set the world ablaze—but eventually the planet will recover, nature will prevail, and you will have future opportunities, like a phoenix rising from the ashes, to go all-in again.
If, though, your goal is to compete consistently each year, then you'll want to have a longer-term and process-focused perspective.
What does this mean?
Positional balance. Quality depth. Constant churning of the waiver wire. Regular exploration of the trade market. Keeping one eye on the future and the other on the present.
And in terms of capital allocation, I think a longer-term approach usually means investing more of your premium draft picks in durable assets (QBs and WRs) and less in changeable contributors (RBs and TEs).
That said, you can't invest everything in QBs and WRs (unless your league has a robust trade market in which you are extremely active, and probably not even then is it a good idea to overindex into two positions). Again, balance is significant when the long term is the priority.
Know Your League
This one is vital.
In a past life, I taught composition to college freshmen, and in my class I tried to drive home the importance of writing for your audience. Yes, I was merely trying to ensure that I wasn't bored when grading papers, but still—audience is important.
In much the same way, your dynasty leaguemates are important. Without them, there is no league. The environment they create is everything.
If you want to take a long-term approach but can already anticipate before the startup draft that the league is at risk of folding within a few years, then you might need to pivot.
Similarly, if you enter the startup draft prioritizing an immediate championship but see that everyone else has the same mindset, then it could make sense to call an audible and zig while the league zags.
And if you draft in the startup as if you'll be able to make lots of trades later, but then realize afterward that the market in your league is almost nonexistent, you'll struggle to have success if you didn't adequately address all the positions while picking.
Or let's say you think you'll be able to dominate the waiver wire because some of the guys slack in their redraft leagues … and then—because they like the format so much—they go hard on waivers in dynasty and make it almost impossible to add any players at a discount. In that case, the draft and trade market will be all the more important.
You can have all the strategies you want when you enter your league, but as a great philosopher once said: “Everyone has a plan till they get punched in the mouth.”
Your plans matter, but if they don't take your Mike Tyson-like leaguemates into account, then you're unlikely to be successful.
Know How to Trade
Many fantasy managers actively try to win every trade they transact. They won't make a trade unless they feel as if they're pulling something over on their trade "partners," whom they don't at all treat like partners.
I think this is the exact wrong way to trade.
The goal is not to win every trade. The goal is to be an active part of the trade market—to ensure that it exists—so that when you need it, it's there, it's robust, and it's accessible to you.
In dynasty, a blatantly lopsided and exploitative trade can poison the well for years, especially if the waterlike market stagnates and ceases to flow.
Does this mean that leagues should have vetoes?
No. Strong no.
Vetoes suck.
It means that the market should be strong enough so that, once someone receives an offer, that manager is immediately able to see if that offer is reasonable via conversations and negotiations with other potential partners.
The trade market should be a true market with many active participants.
With this goal in mind, I believe that trading to win all the time is a substandard strategy, but trading to win in the aggregate and long run is an optimal approach.
Sometimes, your willingness to flip coins in a few trades will give you the opportunity later to hit a big winner when you really need it.
If you're playing to win right away, then fine—I guess you can have an "every trade needs to be in my favor" mindset. It's myopic, but that's your business. If, though, you want to build for the future—and if you care about the health of the league, because without it you can't create a dynasty—then you'll likely care less about winning every trade you make and more about making as many trades as reasonable and trying to make as many people as possible net winners in the market.
In dynasty, being a good trade partner is better than being a cutthroat trade winner.
Know How to Win Now & Later
Earlier in the piece, I asked this question:
When your dynasty league ends, do you want to be able to say that you won a championship? Or do you want to be able to say that you competed every year and had one of the league's best all-time franchises?
And then I said there was no wrong answer.
I lied.
In my opinion, the goal of dynasty … is to build a dynasty. I think it's hard to build a team that wins multiple championships if it doesn't contend consistently, and the best way to compete on a yearly basis is to construct your roster with your eye on the horizon, not the path immediately in front of you.
But I'm also aware of the sad reality that many dynasty leagues fold within five years, which means that the long-term perspective is not always realistic.
And that leaves some dynasty managers in a predicament: Do I try to win now? Or later?
I think the answer is both: Win now … and then win again later.
Easier said than done, but here are two ideas for how to execute the "have it all" approach.
- Trade down in the startup draft.
- Trade players earlier than you think you should.
Trade Down in the Startup Draft
In the startup, league enthusiasm will probably be at an all-time high, which means that your trade partners will likely be more willing to make advantageous offers. If you're willing to part with some of your early startup selections, you can likely accomplish two feats.
- Acquire more starter-caliber picks in the startup.
- Acquire extra premium picks in future rookie drafts.
Let's say that each team has 10 starters and that most of them are drafted in the top 10 rounds. Now let's imagine that you trade your first three picks in the startup, but you get six extra picks in the middle rounds AND three extra first-rounders in next year's rookie draft.
What this means is that now you have 13 picks (instead of 10) to select starter-level players in the startup … and then you also have the amplified ability to load up on rookies the following year.
With your extra startup picks, you can build quality depth throughout your roster, and because you have the extra rookie picks, which you can use to replace aging veterans, you can afford to go after productive but older players who might fall down the board but will probably still be good for at least another season.
Guys like RBs Christian McCaffrey and Derrick Henry, and WRs Tyreek Hill and Davante Adams.
If you look at our Fantasy Life redraft rankings, you'll see that we have all of them as consensus top-36 players. If you drafted them this year, you'd have a chance to win a championship.
But in our Fantasy Life dynasty rankings, only McCaffrey (33) is valued as a top-36 player, and the others are all outside the top 60. Not good.
And yet, if you have extra picks in your startup draft—and extra premium picks in next year's rookie draft—then it could be a totally reasonable strategy to draft McCaffrey, Henry, Hill, and Adams in dynasty, because they could help you win a championship this year, and then next year you could get rookies to eventually replace the veterans.
Trade Players Early
I have a word limit, so I'll be quick with this one, and it's kind of evident anyway: If you trade players earlier than you want, you contribute to a vibrant trade market, and you give yourself the best chance possible of divesting from players at their peak and before their market values and production decline.
It can be unsettling to trade contributors away before you want to, but that's the conundrum, isn't it?
Once you know you want to trade a guy away, once you're ready to part ways with him, it's already too late.
If you want to win now and later, you'll probably need to get comfortable with being uncomfortable trading your guys.
If you trade too early, you might miss out on a championship. That sucks. But if you repeatedly trade too late, you'll eventually find yourself a vassal in someone else's empire.
For more dynasty fantasy football strategy, picks, and more, subscribe to the free Fantasy Life Newsletter—where every Saturday is dedicated to dynasty deep dives.
Premium
Go FantasyLife+
Your league is unique. Your advice should be too. Get personalized tools, rankings, and projections tailored to your fantasy football league settings.
