7 Lessons on Daily Fantasy Sports You Can Only Learn from the Pros

Peter Jennings CSURAM88

Jonathan Bales is the author of the Fantasy Football for Smart People book series and a member of Team DraftKings.

As you might imagine, my latest book on how to win playing daily fantasy sports has been a huge hit with the ladies, many of whom e-mail me 1,500-word breakdowns of their fantasy football teams and upcoming daily fantasy strategies.

Just kidding, those are all guys, but I APPRECIATE ALL OF YOU.

Anyway, my last book has indeed been semi-popular, but that has nothing to do with me and everything to do with the people who basically wrote it—the professional daily fantasy sports players who I interviewed. If you’ve played daily fantasy sports, you recognize the names: headchopper, Al_Smizzle, dinkpiece, naaperstermaan, PrimeTime420, C.D. Carter, Mirage88, MrTuttle05, KillaB2482, and of course the newly $1 million richer CSURAM88.

Each chapter of the book sports an interview with one of the pros, followed by analysis from CSURAM88 and myself. I come armed with graphs, but I make my sections very clear so you can just skip over them and read what the big dogs have to say.

The book is filled with lessons from the pros, many of which are basic heuristics they use to craft their lineups. I’ve plucked some of my favorites from the book, along with some of the pros’ analysis on the subjects.

Lesson 1: “Emphasize both value and matchups.”

–          headchopper

In baseball, it’s 99 percent matchup stuff. It’s basically all matchup-based. In basketball, it’s the opposite end of the spectrum; it’s completely value-based. I know who the great players are in a given night, matchups don’t matter as much, and I’m just looking to see how much value I can get out of you.

I think football is a mix of those two sports. You want the value in terms of the salary, you know, but you also need to consider the matchup. It’s just a unique situation because neither one should be the only thing you consider, or even close.

Sometimes you can kind of disregard a poor matchup if the value is there, and other times a guy might have a juicy matchup and you might be a little more hesitant because of his salary. But you can’t just load up on one or the other. If you’re purely value-based, you might not have the best team just in terms of putting up a whole lot of points. Some guys might be poor values but can just go for 200 yards in any game.

If you’re strictly matchup-based, you’re ignoring a big part of puzzle. If we just stuck to matchups, everyone would have pretty much the same lineup. You can’t just plug in a running back who’s playing the worst run defense or something like that. But I’ve seen plenty of times when good offenses just explode on great defenses and not a lot of people used players from the game because it was considered a bad matchup.


Lesson 2: “Use the Vegas lines differently based on the league type.”

–          Mirage88

In cash games, I think Vegas can really help with your own projections. In tournaments, I think the biggest value from the lines comes in using them as a prediction market for ownership. So the higher the over/under on a game, the more player utilization there will be in those games. Even if the general public isn’t using the Vegas lines, they still have a sense of which games are going to be high-scoring, so Vegas can act as confirmation of where there’s going to be heavy player usage.

That’s important because, unlike in cash games, it’s important to have a unique lineup in tournaments. So if there’s a game that’s an outlier in terms of the projected total, just way ahead of everything else, it’s kind of hard to recommend players from that game because they’re going to be so popular.

That doesn’t mean I never use players from the highest-projected game in tournaments, but if I do, I need to create some elements within my roster that I think won’t be as common elsewhere. It’s not that you can’t win by using all highly utilized players, but just that it can improve your tournament odds by adding at least some contrarian elements into your lineup when you otherwise go with the chalk.


Lesson 3: “Target kickers on good-but-not-great offenses.”

–          Dinkpiece

At kicker, I’m generally looking among the cheapest options because they’re so volatile, but there’s still some nuance to it. A lot of people say they look for the cheapest kicker on a high-scoring offense, but I don’t want the offense to be too efficient or else they’ll steal field goal opportunities.

I like to target kickers on teams with decent offenses but maybe those that aren’t that efficient in the running game, specifically in short-yardage situations. Those teams tend to pass the ball more in the red zone, and passing produces binary outcomes down there; it’s usually either a touchdown or not, which sets up longer third downs and can result in more field goal tries. If you can identify an offense that can move the ball up the field but might struggle punching it into the end zone, that’s a good opportunity for points from short field goals.


Lesson 4: “Projections are useful, but they can be dangerous.”

–          CSURAM88

Daily fantasy players need to be careful when trying to translate their projections into lineups. Projections can be valuable, even if it’s only because of the research you put in to complete them, but there’s still a lot of subjectivity when trying to pick players from a list of values. There are so many players that there are naturally going to be a handful ranked very closely to one another, so you have to be able to pair players in an optimal way without just selecting the top values all the time.


Lesson 5: “Being contrarian is more useful early in the season.”

–          Al_Smizzle

My strategy changes a lot throughout the season. In the beginning of the year, I’m much more likely to be contrarian because everyone is basically picking players based off of season-long ADP, which is mostly based off of the prior season’s stats. Football is such a unique sport in that the data from the previous year isn’t really that meaningful, though; situations change, coaches change, personnel changes, so there aren’t necessarily great numbers to use to determine team or player strength.

For that reason, I’m not as value-based early in the year just because it’s more difficult to determine value. Then, I think there’s a lot more value in going against the grain. As the season progresses, we get more and more data and we can see how certain players perform together or how coaches are calling things. By the end of the year, I care less about projected ownership because I think I can create more accurate values.


Lesson 6: “Pay attention to how you pair players.”

–          Naapstermaan

You can get in trouble if you’re building lineups without any focus on how you’re pairing players together, because that can really increase the risk you’re taking on. If you like A.J. Green, Eddie Lacy, and Rob Gronkowski in a given week and you put 50 percent of the money you’re playing on those players but you limit the number of times they’re paired together, you’ll be in a lot better spot than if you put 50 percent of your money on them but you put them all together in every lineup. If two of them have a bad game or something, you’ll probably have an awful week no matter how the other players perform. Thinking of it in poker terms, you need to leave yourself ‘outs.’ You don’t want to be in a position where you lose everything because of one or two fluke games.

I’m always cognizant of player exposure when I’m creating lineups. For me, it’s just a ‘feel’ thing; I might see I have too much of one player and I need to start working away from him, for example. I also build a general game plan before creating lineups, so I know I want around X amount of this player and Y amount of that player. If you just start blindly building lineups, you can get lost in it and take on a lot more risk than you’re anticipating.


Lesson 7: “There’s not a single ‘correct’ bankroll management strategy.”

–          KillaB2482

I have a poker background, and in poker, a lot of inexperienced players think there’s just one right way to play a hand. Similarly, I think the biggest bankroll misconception in daily fantasy is that there’s one magic formula that’s ideal and going to lead to profits no matter what. There’s not just one way to profit in daily fantasy sports; some pros play only cash games or only tournaments, for example.

There are certain principles that you should understand—like not placing 50 percent of your bankroll into a single tournament lineup, for example—but there are different ways to reach the same result. The specific path that’s best for you really depends on your lineups, risk tolerance, league selection, and so on.

Just consider typical payouts in different leagues. If you play someone of the same skill level as you in a 50/50, you’ll win once every two days, on average. If you play a 1,000-man GPP with the top 200 paid out, however, you’ll win once every five days. Just from those numbers alone you can see that there necessarily must be different bankroll management paths.


Bonus Lesson: “Base your lineups around how you can win the flex position.”

–          The Dumb Author

One of my favorite aspects of daily fantasy football play is how to handle the flex spot. I think that’s the biggest area where an experienced user can gain an edge over a novice, especially on a PPR site like DraftKings, because there are so many different ways to go with the flex spot. It’s the only place where you need to make direct comparisons among players at different positions, which creates an entirely new layer of strategy.

In my last book Fantasy Football (and Baseball) for Smart People, I received data from DraftKings on what strategies are actually winning daily fantasy leagues. Here’s a look at the probability of winning a head-to-head matchup based on which position is in the flex.


It’s pretty remarkable that there’s been so little success for tight ends as flex plays in cash games, but it makes sense; tight ends see the lightest workloads of any skill position, so they’re bound to have the most variance from week to week. Wide receiver workloads are bigger, while running backs are a step above both.

You can enhance your cash game win probability by playing a running back in the flex, and specifically a pass-catching running back. Those players are extremely safe from week to week because they aren’t reliant on a particular game path for points; they can contribute regardless of the score, and there’s safety in that. They also see the most touches, meaning their play has the most chances to regress toward the mean, i.e. you get what you pay for.

If nothing else, the above data is evidence that a safe approach to cash games is indeed the correct way to approach them. That means projecting players’ floors, asking yourself “What’s the worst-case scenario for this player?” For running backs, that “worst case” is typically better than for receivers.

In comparison, here’s a look at GPP win probability based on flex strategy.


It’s the exact opposite, which is even more evidence that safety wins cash games, while volatility wins tournaments. A running back might give you a high floor of points in a given week, but all except the truly elite backs don’t possess ceilings as high as wide receivers on PPR sites like DraftKings.

Note that most tight ends’ ceilings aren’t quite as high as the top running backs, but they’re also typically much cheaper, too. That means that playing a tight end in the flex 1) gives you a high ceiling relative to the cost and 2) allows you to spend big elsewhere.


This new book is a nice complement to Fantasy Football (and Baseball) for Smart People, which is filled with awesome DraftKings data on what’s actually winning leagues on the site. No more creating lineups based on hunches—just the numbers (like those above) to help you win leagues.

Two other quick tips. First, read Justin Bailey’s “Joe 2 Pro” series this year. Really smart guy and it should be an awesome look at what it’s like to manage a bankroll and play fantasy football with money on the line.

Second, utilize the GLSP Projections App. So much of daily fantasy success is about understanding which players have access to certain ranges of potential outcomes each week, and the app allows you to do that very quickly and efficiently.

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