“Writing is a dying art”. That’s what they tell me at least. They say that folks don’t have the attention span anymore for articles. They say that I should condense my content down to a tweet or a video or, if possible, maybe just a gif. I mean, it’s fantasy football, right? Just post the rankings. Why go through all the trouble of learning the material if we can just have the answers to the test?

And, if articles are too long for the average consumer, books are certainly out of the question, right? Who has the time to read an entire book? Especially one that’s not even about football. I must be outside of my MIND to ask fantasy gamers to even consider reading an entire book when everything they need is right there on the YouTube. It’s honestly a preposterous suggestion.

But let’s compromise here. You and me. Here’s the deal: you don’t need to read an entire book if you don’t want to. How about instead you take maybe five minutes max to read this quick article on how three books can transform you into an absolute FORCE when it comes to trading in fantasy football? Just that – one little article. And then you can decide for yourselves if you have the capacity to read a whole book. Deal?




How To Win Friends & Influence People - Dale Carnegie

You might be hesitant to read this book. I was. I thought to myself, “I have friends. I don’t need some nerd to tell me how to make friends”. But enough folks recommended the book that I finally did read it. And, boy, am I glad I did. 

The title undersells this content, implying that it’s only about “making friends and influencing people”. It’s more of a guide on how to be a good person. And, if you’re already a decent person, you’ll enjoy reading it that much more. It reinforces what you are already doing right and, hopefully, smooths over any rough edges you might have.

Some of the key points in this book can DIRECTLY help you in fantasy football trading as well because it’s all about how you talk to people. How you treat them. There are so many fair deals that get blown up because of emotions like pride or greed or even anger. You have to learn to chill out and understand the person you are trading with. Here are the three basic parts of a trade and how the book can help navigate those.


Before you even approach your trade partner, you need to understand them. One of the main points Carnegie drives home again and again is to put the feelings of the person you are dealing with first – even before your own. If at all possible, you should genuinely become interested in HELPING your opponent’s team. Put yourself in their shoes. You aren’t here to rip them off. You’re here to get what you want.

And believe it or not, that can also include giving them what they want, too. Both teams can “win” the trade. So, when you are doing your trade preparation, consider THEIR team first. Where are they in the dynasty cycle? Tank? Rebuild? Competing? Did they just blow up their team for picks and prospects? If so, do you think they are going to want the 33-year-old wide receiver on your bench? Of course not.

Figure out whether they are playing for the future or to win now. Then consider who they currently have on their roster. If they are competing now but they are loaded at wide receiver, they still won’t want your dusty old wideout. It doesn’t matter if it’s a “fair trade” on paper. Try to work out the basic idea of a trade that makes sense for both parties before you even approach them.


How you approach them has a tremendous impact on the results. Even if the offer you are sending or the sentiment you are attempting to convey is EXACTLY the same. Let’s consider a situation where you are in a position to win, and your buddy’s team is pretty bad. In fact, it’s terrible. It’s in his best interest to trade his older players and play for the future. So, you reach out and hit them with this. It’s your buddy, after all, this is how you guys talk.

“Dude your team sucks, man – you’re delusional if you think you’re going to win this year. You need to blow it up. You really should give me your best player for my rookie draft picks and focus on coming in last, get the 1.01. Did I mention that you are bad at this?” 

How do you think that makes them feel? Not great, right? I’d get pretty defensive if you came at me with that, even if we’re pals. The entirety of Dale Carnegie’s book is designed to help you NOT come off that way. Remember: you are interested in helping them. They are your friend. You don’t want to come at them with negativity or criticism. You want to stroke the ego a bit. Talk in terms of their interests. Let THEM come up with the idea. Here is the same sentiment but with a little sunshine on it.

“Sup, dude? You’ve got some nice young pieces on your squad – I like the direction you’re moving in. I’m on the other end, I need to push my chips and go all in. My guys aren’t getting any younger here haha. I’ll probably need to blow my team up in a year or two but I’m in win-now mode. What are your thoughts on a trade?”

Doesn’t that sound nice? Warm and cozy. And you’ve planted some seeds. You let them know you respect them – they are good at this and what they’ve done well is set themselves up for the future. Never mind that their team absolutely stinks, as the future holds amazing mysteries. And you’ve established yourself as a complementary pairing to them. The Yin to their Yang. The old to their young. A viable trade partner. I mean, you’re pretty much on the same team. 

You’ve also not only called attention to your own “mistake” that you are not set up for the future, but you’ve implied that it’s okay to “blow things up”. That’s part of the game. You will need to do it yourself, after all. Heck, maybe you will even trade them some guys back when it’s time for you to rebuild and it’s their turn to win. If we ever stop winning, that is.


You’ve now not only buttered them up but issued them a challenge: find us a trade that helps me win now and helps you win later. If they respond with, “What did you have in mind?”, you have two options. 

You can clarify your “challenge” for them to find a trade where they give away their old guys for your young guys/picks. Or you can just propose the trade you had in mind. I like to at least attempt to let them come up with the idea first. A little inception. It’s much easier to sit back and say “yes” to a trade than it is to convince them to say yes.

So, we’ve approached them genuinely and now we allow them to come up with the trade. But the reality is that we already know exactly what we want. And what we’re willing to give up. Because this next book taught us how to negotiate.




Never Split The Difference - Chris Voss

My background is actually in finance/real estate. Before switching over to this silly job full-time, my last title was Vice President of Acquisitions. I was essentially finding, buying, managing, and selling commercial real estate. Slightly different spreadsheets than my fantasy football ones but analysis and negotiation, nonetheless. And one book drastically changed the way I negotiate. Not just in real estate, but in fantasy as well. It’s called Never Split the Difference by Chris Voss. 

You should read this book. Or at least swap out your podcasts for a bit and listen to it. I’ve done both – it’s that good of a book. There’s no way to encapsulate all of it into a quick summary, but here goes:

  • Chris Voss was a successful FBI hostage negotiator
  • He later went to business school to test his negotiation skills there
  • He obliterated everyone, both in academic competitions and then later in real negotiations
  • He’s now one of the top negotiation consultants

Why is he so good? Well, he never lost his “hostage negotiation” mindset. In hostage negotiations, you can’t just say, “Alright you can kill two but give us back the other eight”. You need all ten. You can Never Split The Difference. Hence the title of the book. And that’s how we should approach trades. Know what you want. Know what you are willing to give up. And never split the difference.

Two Lists

When you approach a trade partner, you should have two lists. The lists will vary from partner to partner and from trade to trade. Different partners are going to have different types and levels of assets, after all. And each asset will have its own list of what you are willing to give up. But the general idea of the lists is simple:

  • List 1 - What you want to acquire
  • List 2 - What you are willing to give up

That’s it. If the team you are trading with is absolutely loaded, maybe you are willing to give up everything – who knows? When it comes to saving a hostage’s life, the list of things we can spare is pretty long. The end goal regardless is to get the players from List 1 while giving up as little as possible from List 2. When all is said and done, you will have given up only expendable assets while adding new players or picks to your group of core assets. 

It doesn’t always have to be perfect. If you put your name on the trophy and the money in your pocket, did you really “lose” the trade? Build the best team you can and win. That’s fantasy football. You’ll want to play your cards right, of course. Don’t start with an offer so insulting that it halts the whole operation. We want to Make Friends and Influence Others, right? 

But don’t just send the max offer right away, either. Then you might give up more than you need, and generating value is still important. As we know, HOW you approach the trade is crucial to the results. Also important is WHEN you approach the trade. This third book may be a little controversial, but stealing some key ideas can help us time the deal right and secure the assets.




The Art Of War - Sun Tzu

I’m not going to lie to you – Sun Tzu seems like a pretty ruthless dude. Some of the advice in this particular book might carry some sociopathic tendencies, to say the least. But he is also talking about war – a life and death situation – and desperate times call for desperate measures. 

We are talking about fantasy football here, so we’re not necessarily trying to murder our friends while they are sleeping under an apple tree and steal their running back. But we can glean some knowledge from this book that will help us accomplish our goals.

A lot of the advice lines up with our first two books as well. But some of the key excerpts I’ve pulled from The Art of War are about WHEN to strike. And how to keep your opponents at bay. This book is absolutely loaded with easily digestible quotes, so here are a few of them we can apply directly to trading in fantasy football.

“It is easy to love your friend, but sometimes the hardest lesson to learn is to love your enemy.”

  • Maybe you’re friends with everyone in your league, maybe you’re not. Maybe Dave is a huge jerk. But the more you understand Dave, the easier it is to trade with him. As Sun Tzu also says, “We cannot enter into alliances until we are acquainted with the designs of our neighbors.”

“Victorious warriors win first and then go to war, while defeated warriors go to war first and then seek to win. Ponder and deliberate before you make a move.”

  • As we discussed earlier, by the time you say, “What are your thoughts on a trade?”, you’ve already analyzed their team and made your two lists. Keep that in mind when someone reaches out to YOU with an open-ended trade question as well. You better believe they have looked at your team and have something in mind. Try to put yourselves in their shoes and figure out what the “black swan” is (you’ll understand what that means if you read Chris Voss’s book).

“The greatest victory is that which requires no battle.”

  • Both teams can win the trade if you consider the timing and needs of both teams – especially in dynasty. It doesn’t need to be a knock-down, drag-out fight.

“The worst strategy of all is to besiege walled cities.”

  • Some folks simply don’t like trading. That’s okay. Don’t waste your time. Same goes with his comments that “there is no instance of a nation benefiting from prolonged warfare.” Negotiating a single trade for weeks on end is equally counterproductive, even if it goes through. At the risk of using 700 cliches in one article, time is money.

“A wise general makes a point of foraging on the enemy. One cartload of the enemy’s provisions is equivalent to twenty of one’s own.”

  • Try to get those throw-ins. We just wrote an entire separate article on The Hidden Value of a Roster Spot. If you can get an extra player you like from their bench or a late draft pick, get it. That third or fourth round throw-in could be the last piece you need to get your next deal done. Or maybe it’s the next Puka Nacua. It’s free real estate. 

“If they will face death, there is nothing they will not achieve.”

  • Here he is mostly speaking about his own troops, but it applies to the enemy as well. And this is the biggest one regarding timing. Let’s say you are a team playing for the future. Your league-mate is playing to win now. He’s willing to go all in. All of a sudden, their quarterback gets hurt. They now face having an older team but not winning. This is the best possible time for you to slide in and trade them that aging quarterback from your team. The value will never be higher. You just happen to have the right piece to help them. As Tzu says, “Begin by seizing something which your opponent holds dear; then he will be amenable to your will.”

“Move not unless you see an advantage; use not your troops unless there is something to be gained; fight not unless the position is critical.”

  • Don’t trade just to trade. Writing this article even has me fired up about trading. But only make moves that are actually advantageous to you. ESPECIALLY if you are playing to win this year and your opponent is also playing to win. A neutral trade on paper can seem fine but keep in mind that you might be disproportionately fixing holes in your opponent's lineup. You want them to be weak. 


"Never interrupt your enemy when he is making a mistake." - Napoleon Bonaparte

  • This one is often incorrectly attributed to Sun Tzu. But it’s a good one, nonetheless. If your opponent sends you a trade that is bad for them, accept it. When the veto calls and group chat jabs from the league come through, let them know that you didn’t propose the trade – they did. I hate vetoes but that is a discussion for a different day. Even if your league does veto the trade, what is the material harm? The trade either goes through or it doesn’t. You either gain or remain even. What are you supposed to do, hold their hand?




Read, Read, Read

At the risk of sounding like an old man, I will say this: you can’t win your fantasy league on TikTok. Put the effort into LEARNING. If you like a tweet or enjoy a 30-second clip that someone posts, then great; take an opportunity to check out their actual work. Read their articles. Listen to their podcasts. Watch their full-length videos. Absorb as much information as you possibly can and then form your OWN OPINION. 

Rankings are cool and all – we offer dynasty rankings to our members and best ball rankings in our Best Ball Cheat Sheet. Those are tremendous tools to help guide you. But they should be just that. A guide. The articles that come with those products are FAR more valuable. Because the strategy, the picks, the trades, the waiver moves – all the aspects of winning – that should come from YOU. And the things you have learned along the way.

This was just one article. And these are just three books among MANY that can help you become a better fantasy gamer. They can teach you to work harder AND smarter. And they’ve personally helped me grow into a better person. Sure, fantasy football is just a hobby. But that doesn’t mean we can’t use it to learn and to grow.

Obviously, anyone can win a fantasy football league. That is, and always will be, the greatest appeal of the game. Winning is fun and we’ll do whatever we can to gain an edge. But it’s the way you handle and represent yourself, both in your leagues and the fantasy community at large, that means more than winning trophies. 

That’s what matters most among those of us who take this silly game seriously. And, if you focus on being the best person and player you can be, the trophies will come too. That starts with taking a few minutes to sit down and read.