The first time I ever played fantasy football, which was almost 20 years ago now, it was in a women-only league.

OK, technically, I wasn't the one playing in it. That was my girlfriend.

But she didn't know anything about football or fantasy football, so she asked me for help, and what was I gonna do: Say no?

So I covertly managed her team in the league she had with her best friends, and then the next season, I decided to do the thing right by actually joining a league of my own.

Ever since then, I've been obsessed with fantasy, so much so that a decade ago, I basically had to turn sports analysis into an actual career or I'd be a dude without a job.

But deep down, I'm still just a guy who in 2006 stupidly drafted RBs Shaun Alexander and LaMont Jordan in Rounds 1-2 and finished 10th in a 12-team league comprised solely of sorority sisters.

Please, learn from my mistakes.

Also, I've probably gotten better since then.

Here are my 10 pieces of advice for first-time fantasy football players.

10 Tips For A First-Time Fantasy Football Player

Have Fun

If this is your first time playing fantasy, you're probably in a league with friends, family, coworkers, or at least acquaintances you like.

Have fun with it. Don't take it too seriously (assuming you don't have a serious sum of money riding on the outcome).

Fantasy football for you should be a leisure activity, something you do for recreation and happiness.

So whether you finish first or last, try to enjoy the journey.

Destroy Your Enemies

You know what helps make fantasy fun?

Winning. 

And not just winning—but absolutely destroying your leaguemates to such an extent that they start to question their life decisions … like being in a league with you.

Fantasy should be fun—but only for you. It should be absolutely awful for everyone else, because they have no chance of matching your alpha dominance.

If you're going to play, then play to win, and anything worth doing is worth doing well—so don't just play to win: Play to annihilate your enemies.

Enemies?

Yes, enemies.

I mean, don't tell your leaguemates that they're actually your enemies. Don't act like a sociopath.

It will be easier to destroy them if they think you're their friend, at least at first.

Don't Drink During the Draft

What's the kind of thing that a "fake friend" would do to give himself a better chance of winning at fantasy?

Oh, I don't know, maybe offering to host the in-person draft at your place, providing everyone with alcohol, and then dominating the draft because you decided to stay sober under the auspices of “I'm hosting the event, I don't want to drink because I need to be a capable master of the house, and I also must make sure that all you drunk morons get home safely after I legally rob you in the draft.”

Don't act like a sociopath … but definitely be a sociopath.

All kidding aside: Consider not drinking during the draft. Most people tend to make suboptimal decisions when imbibing alcohol.

If you drink during the draft and then make a dumb decision—like drafting Shaun Alexander in Round 1—then you'll need to live with that decision for the rest of the season. And maybe even the rest of your life.

I know it's fun to hang out with your buddies while eating buffalo wings, drinking tasty adult beverages, and pretending that elite athletes who make millions of dollars actually play for your team—but if you can resist the temptation, don't drink while drafting.

And if your leaguemates just so happen to drink while drafting, then all the better for you.

Also, this is kind of related: Maybe avoid eating any rich or uncommon foods before or during your draft. The last thing you want to do is autodraft a supermajority of your team because you need to spend time on the toilet.

Just saying.

Have a Strategy

It's not enough not to drink during your draft. Entering your draft, you should also have, you know, a plan.

What you do in the draft will be dictated to some extent by your leaguemates, but that doesn't mean you shouldn't have a strategy. It means that you should have multiple strategies, which are accompanied by contingencies.

For example: As I note in my updated "Freedman's Favorites" for 2025 fantasy drafts, I generally want to wait on QB, address RB in the middle rounds, attack WR early, and find value at TE if I miss out on the top two.

That's a plan.

Sometimes things don't go according to plan, so it's always good to have an idea for how you might adjust your strategy based on circumstances—but, again, that's planning.

I guess I'm saying that you shouldn't go into your draft with the attitude of "Let's see what happens."

Your approach should be: “I hope to do X, Y, and Z, but if A, B, and C happen, then I'll pivot to L, M, and N.”

Don't ask me why I picked those random letters. I have no idea. 

Talk Trash

In my opinion, there's no wrong time to talk trash—except maybe after a loss.

And hopefully that gives you all the more incentive not to lose.

But at another point in the year—before the draft, during the season, after you've beaten someone in a head-to-head matchup, after you've won a championship to wrap up an undefeated season—it's fine to talk trash.

In fact, it's more than fine. It's mandatory—because it ties in with the first two items on the list.

  • Talking trash is fun.
  • Talking trash—when done right—serves to destroy your enemies.

And by "done right," I don't mean something mundane, such as, “You suck.”

It has to be something like: “Remember that time in eighth grade when we lost a playoff game because you dropped a flyball and then everyone hated you? Somehow, you were even worse than that this weekend when you set your lineup.”

Really give it to them.

Don't cross a line, of course—because that will make it harder to get deals done in the trade market (more on that later)—but definitely touch the line.

Side note: I think some of the best fantasy team names are in the "trash-talking" vein. It's great to have a creative and funny moniker. It's even better if it also manages to insult someone—or, even better, everyone—in the league. 

Shoot for Upside

Remember, it's not enough to win. You really want to humiliate everyone in the league by having by far the best team.

And that means you need to focus on upside.

Here are two ways to do so.

  1. Stack correlated players from the same teams.
  2. Focus on players with undervalued ceiling potential starting in the middle rounds.

Regarding stacking: If you select WR Justin Jefferson, then maybe consider adding QB J.J. McCarthy near the end of the draft. If Jefferson goes off—and you just invested Round 1 capital in him, so you're presumably planning on him having a successful season—then that means McCarthy will also have an elevated chance of putting up useful numbers.

By stacking, you give yourself leverage, and you also limit the number of football-based insights you need to get right.

Regarding focusing on players with high ceilings relative to their draft range: If a high-floor Round 10 guy modestly outperforms his draft position, that will benefit you little, but if a high-ceiling Round 10 guy smashes expectations, that might win you the league.

After Round 5 or so, what matters is not so much the odds of a guy outplaying his draft capital. What matters is the extent to which he might do so. The force of the potential impact trumps the probability of its occurrence.

Wait on Kicker and Defense

Kickers matter. Defenses matter. But they're also incredibly hard to predict.

Don't draft them before the final two rounds.

In fact, if your league rules allow, don't draft them at all.

Instead, add two upside RB handcuffs who might turn into breakout stars if the starters ahead of them happen to hold out or suffer some sort of preseason injury.

Remember James Conner in 2018, when he put up 1,470 yards and 13 TDs in 13 games because Le'Veon Bell randomly decided to sit out the entire season?

Conner was regularly available in the final rounds of fantasy drafts that year.

Stuff like that doesn't happen all the time—but it happens more than a K or DST being the driving force behind a championship run.

Know the Rules

This one feels basic, but it's important for obvious and subtle reasons.

If you don't know the rules, then you'll make stupid mistakes throughout the draft and season.

But, more importantly, if you know the rules, then you'll be able to draw insights and make inferences that help you.

If you know the rules—and see that you don't actually need to draft a K or DST but instead have the flexibility to load up on other positions, see what shakes out in the preseason, and then add your K and DST right before the season starts—then you you can use that knowledge to your advantage.

In The Big Short, Michael Burry actually reads all the loan prospectuses to determine that the housing market is inflated, and he makes billions of dollars from that acquired knowledge.

Be like Burry. Read the rules.

Work the Waiver Wire

Too many fantasy newbies put all their attention on the draft and then too little attention on the waiver wire.

The draft is important, but so is the waiver wire. In fact, in some formats—like Guillotine Leagues—waivers might be even more important.

The draft is like a wedding, but the waiver wire is like a marriage. Anyone can have a fun wedding, but to have a successful marriage, you need to put in consistent work.

And if you have a wedding, whether it's big or small, lavish or modest, generally, the goal is to have a successful marriage.

Put in the work on the waiver wire.

That's how championships are won.

Don't Overdo It With Trade Offers

In my experience, a lot of fantasy newbies can annoy leaguemates by spamming them with trade offers—especially bad ones.

Don't be the dude who offers someone two late-round WRs for an early-round RB right after the draft. And don't be the dude who sends someone 20 trade offers, even if a few of them are decent.

The trade market is important, and you want to be able to tap into it when you need it.

In order to do that, you need to be a serious and respectful potential trade partner.

Make real offers that are fair to both parties, and—without insulting the intelligence of others—tell them in as brief a manner as possible why you think it's a win-win trade.

That said, there's one exception—and it's a very important one—to everything I just said: In the name of having fun and destroying your enemies, you can occasionally send an obviously unreal and terrible trade offer as a way of talking trash and joking about how bad someone's team is.

When done right, this is a classic move that the entire league can find hilarious.

And if they happen not to find it hilarious, then screw them.

They're just bitter about your undefeated record, right?