Fantasy basketball – How to win your fantasy league

People ask me all the time for tips on how to win their fantasy basketball leagues. I love having those conversations, and I’ll typically go as far as someone wants as far as the level of advice.

What I tell my father-in-law or my children on how to get into fantasy leagues is a lot different than what I’d tell someone that’s been playing fantasy hoops every year for 20 years and is looking for Jedi-level tricks to get that little bit of edge.

For this space, I’ll address the group of people that lives in the middle of those two extremes. But if you’re the latter, and want to dive deep and/or get specific about your questions for your specific league… definitely hit me up on Twitter @ProfessorDrz.

The Draft

The draft is one of the most fun parts of fantasy sports, and it’s also how you set your team up for success. Is it still possible to win a league if you had a bad draft? Yes, it is. But man, a great draft makes it so much easier to win if you start off with the type of strong foundation you can get through the draft.

The first advice I’d give for drafting is make sure to take some time to prepare. I’ve been playing in fantasy leagues for decades, and I’ll have draft-day conversations all the time with friends that say, “Hey. I haven’t looked at this league much, yet. You got rankings or something I can look at?”

The answer is, of course, yes — I’ve got rankings for you to look at. These days, those rankings are on ESPN. Which means that literally everyone in the league has those same rankings to work off. Don’t get me wrong, it’s important to have rankings. But, it’d be even better if you had a good idea about why players are ranked where they are, so you can decide if you agree with the rankings and adjust accordingly.

To do that, you’d need to be paying attention to NBA offseason coverage. What players have moved in free agency and offseason trades, and what were the fantasy ramifications of those moves? Which young players finished last season much stronger than their season averages and seem likely to make a leap this season? Who were the most impressive rookies coming out of the NBA Draft, or even better, coming out of the NBA Las Vegas Summer League?

Answering these questions are key to your draft prep. They should also be fun to answer, because it just means that you learn more about what’s going on in the hoops world. You’re not studying for a test, you’re instead digging further into the sport that you love. And by doing so, it puts you in a better position to win your leagues.

Winning strategies

It’s important to know the scoring system you’re playing, and to draft according to it. A points-based league will have a different set of expectations and necessities than a roto league, which is also different than a roto head-to-head league. Category specialists are more valuable in the roto-style leagues than points-based, whereas efficient volume scorers that don’t contribute across the board or that may have a horrible FT% on high volume may be more valuable in points leagues. Draft accordingly.

It’s just as important to know your history when it comes to the players. These days, there are a lot of players with a huge dichotomy between their per-game potential and their history of game-to-game availability.

Kyrie Irving and Ben Simmons may both project to top-20 producers on a game-to-game basis. But, between them, they missed triple digit games last season, for a variety of reasons that it’d behoove you to understand.

Kawhi Leonard may have a top-10 per-game average, but his load management history suggests strongly he could miss up to 25% of the games even if he doesn’t have an injury relapse.

LeBron James and Kevin Durant could challenge for number one in terms of per-game averages, but they’re both at the stage of their careers where they’ve been typically missing major swathes of games. You need to keep these types of things in mind, before you decide whether to spend a first, second, third or fourth round pick on these types of players… or whether you want to let someone else in your league deal with the situation.

Start building your team around the best players available moreso than drafting for team fit. Particularly for the first few rounds, it’s better to build around the players that will generate the most points than worry about whether you have two or three of one position over another. With that said, Jedi-level drafting will pay some attention to position scarcity, but as a tie-breaker as opposed to a leading factor.

If I’ve got a choice between a player that I believe will average 55 fantasy points vs. one that’ll average 50, for example, I’m taking the former every time. But, if I’ve got a choice between two players that I think will both average about 50 fantasy points, and one plays a position where there are plenty of producers available even into late rounds (say, point guard) while the other plays a position where the talent falls off quickly (say, small forward), then in this case I’d be more likely to draft the latter.

Middle and later rounds

Now, in the middle rounds of the draft, I typically start paying more attention to team fit and making sure I have strong contributors across the board. By rounds 5-8 I’m also making sure I don’t have any position holes that I don’t think I can adequately fill in the later rounds.

And speaking of the later rounds, since by then I already have my foundation in place with sufficient positional flexibility, when it gets to the late rounds I’m shooting my 30-foot Steph Curry-like bombs with my picks. I’m going after my sleepers. I’m taking more chances. I’m leaning into more risk-reward type plays, instead of just going with steady contributors.

Often, it’s the players taken late in drafts that hit that end up being champion-making picks.

Think a level deeper

Think about where your players of interest are in their careers, and how that might affect their production. You want to draft younger veteran players that are trying to carry their teams into postseason consideration… they tend to be more durable and play more minutes because they’re younger but have their NBA legs under them. And they have to do everything they can to get their teams to the promised land.

On the other side of the coin, maybe you think twice about bringing in players that may be the best in the game, but they’re older and playing on teams that are championship-or-bust… and therefore will have an eye on staying fresh for the postseason as opposed to going all-out every game for the regular season.

Another next level thing to keep in mind, that may be trite but also contains truth: pay attention to players that may have some contract year motivations. For example, I already mentioned about Irving’s history of missing major swathes of games. However, this offseason he had a majorly publicized contract disagreement with his team, and thus next offseason he will be negotiating his next big deal.

ESPN’s Stephen A. Smith has suggested that Irving might even be an MVP frontrunner this season because of his motivation level. These types of considerations play into fantasy hoops expected production as well, and you should be prepared to judge accordingly.

Early season and free agency

Be flexible and ready to make moves, right out the gate. One habit that I had to change was relying too heavily on my “draft brilliance,” even once the season began and initial information was different than expectation. If my 13th round sleeper starts off the season on the bench or playing poorly, but there’s an undrafted free agent that’s scored 20 points in the first two games, I have to be willing to drop my drafted player to move onto the better prospect.

I see those first couple of weeks as crucial, because many overlooked players will make themselves known early. And you’ve got to be ready and willing to give them a try early, before your competition does.

Another decision that can be tough is deciding whether to move on from injured players… or whether to stash them. To me, it’s all a question of potential reward vs, availability. In order for me to stash an injured player, that player has to be significantly better than any player available on the free agency wire. The roster composition on my team also has to be strong enough to survive having an injured player on the bench. ‘Injured list’ spots are crucial, and allow more stashing.

Similarly, weekly transaction leagues may not require as deep of an active bench as daily transaction leagues, where volume of player availability absolutely helps determine weekly wins and losses. In a daily transaction league with no injured list and/or shallow benches, I’m not stashing any player short of a superstar.

If I’m in a team with 10 or fewer teams, or with fewer than 13 roster spots per team, I’m also much more likely to move on quickly from injured players because the free agency wire is likely to have more productive players and the line between what can be found on the wire vs. the average rostered fantasy producer is even thinner.

In a 10-team league that starts 10 players with three bench slots, the production of a ‘fantasy starter’ ranked in the 90s and the 131st ranked player on the wire is going to be similar enough that it’d make no sense to stash that injured player on your bench for six weeks instead of getting the production of the 131st ranked player for all that time.

Trading

I’m a firm believer that trading is the absolute key to winning championships in fantasy sports. Very often, at the end of the season, the teams that have pulled off the most trades tend to be clustered more toward the top of the leagues. Trades are your opportunity to look at your teams, identify strengths and weaknesses, and identify specific players to acquire to help accentuate the strengths and/or minimize the weaknesses.

To that end, there are important methods for making good trades. First, you need to really understand your team. Did you come out of the draft with any clear positions that weren’t up to standards? Did you end up having to rely on a player(s) with a history of injury or high risk/reward, without a suitable backup and/or level of redundancy? Or, conversely, do you have great depth but not enough pop in your starting lineup such that you’re unable to maximize your daily output with too much firepower on the bench?

Take some time to evaluate your team, so that you know exactly what you might hope to gain in a trade on a more granular level than just “I want to get better.” Next, evaluate the other teams in your league. In my best league performances, I not only know my own team’s strengths and weaknesses, but I also know the same for the other teams. This is crucial, because it always takes at least two teams to trade. You can come up with trade ideas to get every great player in the league, but if your league mate(s) don’t get what they need out of the bargain, there’s no impetus for them to make a move.

I like to come into any trade negotiation with a logical reasoning for why the opponent should make the move, then build a deal so that they very visibly get what they want/need… while of course assuring that I get what I want as well.

Also, when you’re ready to trade, know the personalities of the team managers you’ll be dealing with, because the way you approach a trade negotiation will need to be case specific.

Some managers may respond well to you just sending them an offer, but in my experience, most won’t. For some, adding a sentence or two of reasoning in the trade ‘comments’ area may be enough. For others, it might be best to send them an email with trade thoughts before you send any offer. For others still, I’ve found it best to call or text them about another topic entirely, then casually bring the conversation around to the fantasy league, and nudge the conversation along until you get them to bring up the topic of a trade. If they feel like the trade is their idea, they’re more likely to say yes.

It’s up to you to figure out the trading personalities of the people in your league, and to tailor your approach accordingly to maximize the likelihood of success. I like to trade early, and often. If you only operate off the draft, or maybe only do one or two trades in a season, it adds pressure to your evaluation skills early, because your team won’t have much opportunity to improve. But if you trade often, it gives your team multiple opportunities to course correct and improve, even as the season progresses.

Final tips

Finally, and most importantly, have fun. Have an absolute ball.

Set up a group Zoom for your league on draft night, so all the team managers can talk trash to one another. Or, if possible, draft live.

If you’re the defending champion in your league, show up to the draft with a WWE-style championship belt.

Make the manager that finished last the previous season buy everyone’s drinks on draft night.

Personalize it. Make everyone love the league.

Once the season starts, maybe have some game-watching parties as a league. Either in person, or over Zoom.

Watch as many games as you can… I know one of my best investments when I got into fantasy sports was purchasing NBA League Pass for sheer enjoyment in addition to helping me keep up with my players and see for myself who I wanted to have on my team vs. potentially trading away.

Set up group chats or text chains. Create more opportunity to talk your stuff, bond and enjoy your league mates.

Not only do these things help motivate you to build a team that’ll win, but they also help make your league super enjoyable and a daily joy for the next six or seven months of your life. If you can do that, then it’s like you already won… OK, maybe that’s a step too far.

Having a fun league is great but if you follow the advice in this article, you will hopefully put yourself in good position to take home the title. And trust me when I tell you — there’s nothing more fun than winning!