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Justin Phan

Fantasy Basketball: Head-to-Head Guiding Principles

Justin Phan
Roto Arcade

Fantasy basketball purists are quick to shoot down the legitimacy of head-to-head leagues, claiming that it is largely luck-based and ultimately comes down to a two-to-three week stretch of the season where statistics tend to significantly fluctuate from the norm. There’s no denying that there is some validity to these claims, and I can’t say I’ve been a staunch supporter of the playoff format itself either. There are some ways to get around it and certain steps that can be taken to minimize the role that these end-of-season fluctuations play in determining the final standings (e.g. moving up the playoffs and cutting out that last stretch when coaches most frequently rest their star players), but in the end it is what it is.

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Where these purists see luck, I see a crossroad where preparation and opportunity meet. The beauty of head-to-head leagues goes beyond the simplicity of facing off against a new manager every week and being able to regurgitate the canned insults you heard on that recent re-run of Yo Momma. It lies in finding that fine line between which player is the best fit for your roster and which player is, well, the best. It lies in the spectrum of competing strategies vying for that spot atop the standings at season’s end.

Head-to-head basketball is a complicated game with many intricacies that often go unnoticed but can end up being the difference between first and second place. Using five guiding principles, Phil Londen and I will outline what some of these potential difference makers are and explain the impact they will have on your strategy come draft-day. Sections written by Phil will be followed by the signifier (PL), while those written that I've written will be indicated with the (JP) tag.

Principle #1: A successful draft begins with preparation.

The plan itself is simple, but the execution of the plan is what separates the consistently successful managers from the masses: come prepared for the draft. The first step to proper preparation is to stay apprised of off-season developments prior to the beginning of training camp. Coaching changes, off-season injuries, national team commitments (or lack thereof), position battles, trades and free agent signings all have an impact on fantasy values. In addition, other factors influence values, including contract status, potential trades (e.g., Carmelo Anthony(notes)) and even extenuating circumstances, such as Mo Williams’(notes) now-infamous remarks about contemplating retirement because of LeBron James’(notes) decision to leave Cleveland. Are you dropping Mo down a couple of spots because of his comments? Most people certainly are, whether consciously or not. Given the vast amount of data there is to process and interpret, draft preparation is not to be rushed and is the foundation for a successful season.

Once you form initial impressions of fantasy values, it is time to really dig in and break it down further. Analyze your fantasy provider’s opening ranks (O-Ranks) for both overvalued and undervalued players. O-Ranks are extremely influential on where players will be drafted and often influences sleeper status. Speaking of draft position, a set of quality average-draft position (ADP) rankings is another invaluable tool in your draft preparation toolkit. The key is finding ADP data derived from knowledgeable managers, and not auto-drafted leagues, which simply mimic and reinforce O-Ranks in a feedback loop. Examining discrepancies between ADP data and O-Ranks is an excellent way to look for undervalued and overvalued players.

In addition to these rankings, a thorough schedule analysis is another set of data to consider during draft preparation. While much of the schedule analysis is focused upon the head-to-head playoffs, there are actually other subsets of data that are more influential: quality games and ironically, the schedule during the first few weeks of the season. After all, if you don’t qualify for the playoffs based upon your regular season play, you never get to take advantage of favorable playoff schedules. Playoff schedules should be more of a focus around the middle of the season when you have a better idea of where your team stands and can start building towards a strong finish. Quality games (games when relatively few teams are playing on a particular day) are arguably the most important games to consider when analyzing the schedule, as quality games allow you to maximize the number of games played each week. Unlike rotisserie leagues, head-to-head leagues generally rely more heavily on being able to maximize games played.

The final element of draft preparation is getting to know your opponents. Chances are that you compete in leagues with the same group of managers year-after-year and you know your opponents in other contexts (also known as real life). Use any information at your disposal to your advantage. What team does he or she root for (i.e. which players are he or she likely to overvalue)? What are his or her draft tendencies – big ball or point guard heavy? Who does he or she have a man crush on, or just plain despise? While it’s not exactly The Art of War, there is something to be said for getting inside the head of your competition and learning about their tendencies and preferences prior to the draft. If nothing else, it gives you some good ammunition for draft-day trash talking. (PL)

Principle #2: Be aware of your competitors and react accordingly to their decisions.

Before we get into the theoretical basis on how to build a successful head-to-head squad, there’s a somewhat contentious (and perhaps touchy) fact of life that must be pointed out: it’s not all about you. Yes, you heard me. It’s easy to get completely wrapped up in putting together your own team to the point that you forget to keep tabs on what your competitors are up to. This can be a major pitfall depending on the size and settings of your league. Size is a major player here (no Greg Oden(notes) or George Hill(notes) jokes … promise). The deeper your league is, the more important it is to pay attention to similar competing strategies that are in play.

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Say you’re picking at the back end of a 16-team draft and the following players are taken in front of you: Chris Paul(notes), Stephen Curry(notes), Deron Williams(notes), and Rajon Rondo(notes). Going small ball and grabbing Jason Kidd(notes) and Chauncey Billups(notes) at the turn is a viable option, but would it be the most optimal play in this circumstance? Definitely not. With four other teams already going for a similar small ball approach (an emphasis on assists and steals), this approach is not only a redundant one, but one that only increases the natural advantage in value that the owners in the first half of the draft order have. You’re essentially playing into the hands of the CP3 and Deron owners here by trying (and most likely failing) to best them at their own game. With multiple teams already targeting similar categories, this, by extension, means they will also be targeting the same players. In this circumstance the optimal play would be to go down a road less traveled and change up your strategy/approach, even if it means sacrificing a little value at the top. The flexibility you will gain in the later rounds will be well worth it as you won’t be faced with these potential limitations as the draft goes on.

You tend to see a lot of ‘reaches’ in head-to-head drafts where managers choose to punt categories and target players that fit their team identity, so be aware of which players you can afford to let slide (usually the more efficient types – Ray Allen(notes), Jason Terry(notes)) and which ones are hot commodities who fit into the specific team concept of the managers drafting around you. It could mean the difference between getting both of the players you want and just one of them. Also be on the look out for the types of players certain managers are drawn too – there are some who prefer to play it safe and grab a LaMarcus Aldridge(notes) in the fifth round, and there are others who are hell bent on grabbing young talents like Anthony Randolph(notes) instead. Every manager has a certain tendency and idiosyncrasy, and it’s up to you to figure out what it is. (JP)

Principle #3: Build around strengths to establish an identity.

The term ‘punting’ gets thrown around way too much for my liking when it comes to building a head-to-head team. The goal should not be to go into a draft with the mindset to explicitly punt certain categories; rather, it should be to develop a core group of categories that you can count on for consistent wins while developing a group of supporting categories that you are competitive in on a weekly basis. Your team’s identity should be built around your strengths, not your weaknesses. Successful head-to-head squads will focus in on three-to-four categories that will make up the team’s core strengths, areas where the team is expected to excel in and win the majority of the time. To supplement these core categories, owners should also aim to be average-to-above average in three-to-four more categories, areas where the team can be expected to regularly compete and win more than half the time.

Punting categories is a necessary byproduct of this process that allows you to maximize and reallocate value to your core and supporting categories, but it should be done in moderation. Punting four categories is an absolute no-no, and punting three is only appropriate in the right circumstances (e.g. deeper leagues where the talent pool is thinner and category fillers are harder to find). Abiding by a two or less punt strategy will keep your team from being pigeonholed and trapped in a corner in case things go awry. (JP)

In building a coherent head-to-head team, a common mistake is to build a core to the point of statistical overkill. Often, too much value is focused upon core categories and not enough attention is paid to the supporting strength categories. You can apply rotisserie league strategy to head-to-head leagues – winning a particular category by 100 is no better than winning it by one, and the same can be said for individual categories in a head-to-head matchup each week. Winning a category each week by a small margin can be thought of as an efficient win, while winning by an oversized margin should be considered an inefficient win. Efficient wins allow you to devote more resources to developing strengths, which in turn can go a long way toward determining whether or not you make the playoffs. As the season progresses, periodically examine your team’s win-loss records looking for opportunities to reduce inefficient wins by trading statistical overkill in order to develop supporting strengths and maximize your win-loss percentage.

After you’ve established a core and supporting strengths and minimized your statistical overkill, you can focus your attention on finding some sleepers late in the draft. Ideally, you’d only draft sleepers who fit the core strengths you’ve established in the early and middle stages of the draft, completing the coherent team you’ve worked so hard on assembling. However, narrowing potential sleeper targets to only players who fit your core forces you to miss out on potential home runs (Stephen Curry last year) for a player who is a better fit. Ignore the core. If you end up hitting on a player like Curry last year even though he isn’t a perfect fit for your squad you can easily trade him for players who are a better fit. The critical point is selecting players who are most likely to succeed and be valuable trade assets. After all, if you’ve done your job in establishing a core and supporting strengths in the early and middle rounds selecting players who fit your system becomes overkill, so the emphasis here should be on overall value instead of core/strength specific players. (PL)

Principle #4: Maintain flexibility to maximize value.

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At the risk of sounding too theoretical, there are actually multiple ways to define fantasy value. One way is to define it as market value, or the value managers are willing to pay for someone’s fantasy production. Of course, this value is relative and is shaped in part by things like O-Ranks and ADP. However, there are often distortions between a player’s market value and his actual, or intrinsic, value. Identifying intrinsic value in a way that takes advantages of disconnects between market and intrinsic value is a prerequisite to being a great fantasy manager. While this may seem likely a strictly theoretical discussion, these ideas are played out daily in fantasy leagues in the form of the buy low and sell high. A buy low is a situation where the market undervalues a player’s intrinsic value. In contrast, a sell high is where the market overvalues a player’s intrinsic value. Another caveat worth mentioning is that your particular team strategy (i.e. core and strengths) can impact a player’s intrinsic value – remember value is relative. Being flexible allows you to take advantage of distortions between market and intrinsic value as the opportunities arise, even though you may not have been targeting a particular player at the outset of the season. Head-to-head leagues allow for greater diversity of tea builds compared to rotisserie formats, meaning there are opportunities to take advantage of wider spreads between market and intrinsic values than in rotisserie leagues.

On a more practical level, positional eligibility is one area where managers are often too rigid in their game planning. Effective head-to-head strategy generally calls for having at least three players that are eligible for any one position on board (or four if there are two of the same position, most commonly two centers) in order to minimize games forfeited due to positional eligibility shortages. With that said, managers frequently make the mistake of putting a rigid system in place where they must have X number of a particular position by a certain round. These concerns should be saved until the latter rounds of the draft with the emphasis in the early and middle stages of the draft completely focused upon maximizing value and establishing an identity. This is achieved through flexibility. After all, positional imbalances can be corrected via trades or waiver wire moves later. Leaving value on the table for something that is so easily correctable later is a losing strategy. (PL)

The idea of maintaining flexibility plays right into the third principle, and is why it is important to go into your drafts with the aim of building around your strengths rather than ignoring your weaknesses (punting). You sacrifice flexibility with every category that you choose to punt, as it only further limits the player pool from which you can choose from and limits your ability to weather key injuries to major personnel during the season. Flexibility is a highly undervalued and often overlooked commodity because it gives you the freedom and ability to capitalize on golden opportunities that arise both during the draft and in-season. Often times, managers are forced to pass on value picks that present themselves during the draft or pass on a buy low opportunity in-season because that particular player does not fit their team concept. These opportunities come few and far between, and a team that lacks flexibility will not be able to maximize value and take advantage of them when they come along.

While Dwight Howard(notes) has become all the craze in head-to-head leagues because his value catapults from 53rd to second overall if you take away his free-throw percentage, there is some unacknowledged downside here. Owning him can be a curse in some ways though because he comes with a rather rigid strategy for one to follow from the outset. One of the downsides to being locked into a particular strategy early on is that it often leads towards tunnel vision, where a manager begins to focus solely on drafting players that fits into his or her rigid team concept rather than on the ones that will offer the most overall value. This is a dangerous road to walk down and should be avoided if at all possible. Whether or not you end up with Howard or Dirk Nowitzki(notes) in the first round, it is important to keep some options open and to be prepared to alter your team’s identity should a significant opportunity present itself. (JP)

Principle #5: Take calculated risks only when the reward is sufficient.

Two terms that I always reference when assessing a player with considerable risk are his ‘ceiling value’ and ‘floor value’. It is essential that you realize what a player’s range is, so you know how high the payout is if he plays to his potential and how much he will end up costing you should he disappoint. The greater the range between a player’s ceiling and floor value, the more likely it is that that player should be avoided in the early stages of a draft. It is highly recommended that you minimize the risk you assume in the first few rounds, because it is at this stage of the draft that leagues can be lost, not won. It is certainly possible to overcome a sixth-round bust, but the same can not be said if your first- or second-rounder blows up in your face.

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Conduct an honest assessment of your own appetite for risk. Some managers are inherently risk-takers and some managers are very conservative. Don’t fool yourself. The ideal spot to be on the spectrum is somewhere in the middle. You don’t want to be the guy who is consistently duped into drafting Andrew Bynum(notes) and Greg Oden in the fifth round year-after-year just because they’ve flashed top-40 upside. On the flip side, you don’t want to be the manager who plays it too safe and doesn’t take enough shots to differentiate him/herself from the pack either. While some prefer to chance it with the oft-injured, my philosophy on calculated risks has always been to opt for young career-year candidates instead. I will pass on the Oden’s and Bynum’s and take shots on guys like Jrue Holiday(notes), Nicolas Batum(notes), Roy Hibbert(notes), and JaVale McGee(notes) later – reason being I don’t feel comfortable grabbing significant injury risks (or character risks, e.g. Gilbert Arenas(notes)) in the first five-to-six rounds. This is by no means the only approach, but it is the one that has worked for me. (JP)

In any context, reward comes with some degree of risk, whether the risk is financial, emotional or physical. Fantasy basketball is no different, with the terms of risk versus reward commonly embodied in injury-prone players. However, the injury-prone label is often assigned liberally, without fully considering the specific factual circumstances at play. For some players, the propensity for injury is a natural byproduct of their style of play (Dwyane Wade(notes), Gerald Wallace(notes)). For others, a number of injuries can stem from an initial injury of a more random nature (Gilbert Arenas, Elton Brand(notes)). And still others experience a high rate of injuries because their bodies are freaks of nature (Yao Ming(notes), Greg Oden) that simply cannot handle the full rigors of the NBA schedule. These are just a few examples, all of which have a high ceiling if healthy. But these categories of injury-prone players are not all created equally. A player like Wade whose injury-prone status is a result of his style of play can reduce his chances of getting injured by changing elements of his game. A player like Oden can’t change his chances of injury because his body itself is the root cause. In rotisserie leagues, injured players are easier to carry due to games played limitations for each roster spot, which curtails churning. In head-to-head leagues, however, maximizing games played is crucial to team success, especially if your league has no restrictions on move limitations. Understand which players have serious injury history and the extent of the injury history when you weigh the risk of injury against the potential rewards of fantasy production.

Taking it one step further, there are a handful of seriously injured players that get drafted every season based upon a risk-reward analysis. At some point, managers determine that the potential reward justifies the risk of taking on an injured stud. This season, Yao Ming, Greg Oden, Andrew Bynum, Mehmet Okur(notes) and to a lesser extent Andrew Bogut(notes) are all injured to start the season. Note that all of these players are big men (coincidence?) and are being drafted and stashed with the temptation of elite fantasy production keeping these players off the waiver wire. Keep in mind that any dead weight carried reduces the number of total games played, putting you at a competitive disadvantage relative to competitors with healthy rosters. Remember, you’ll inevitably end up with in-season injuries to carry. Conduct extensive research if you are considering drafting a player who will not be fully healthy to start the season and determine when the risk of a lost season due to injury is outweighed by the potential reward. The worst mistake a manager can do is to draft and carry an injured stud for part of the season only to dump him because your team fell in the standings. The time spent occupying a valuable bench spot is wasted and can never be made-up. The opportunity cost is real, making due diligence especially vital when dealing with injuries and injury-prone players. (PL)


The head-to-head strategy principles discussed here are meant to be a guide and are by no means exhaustive. There are a variety of different ways to apply these five principles to real life situations, which we will expand upon in a later piece. The main unifying theme that connects these five principles of head-to-head strategy is analysis-based preparation. While you can’t guarantee yourself a championship by applying these five principles to your teams, you can greatly increase your chances of being the last man standing at the end of the season. After all, that is really all you can hope to do, and it is an inherently worthy goal for no other reason that it makes you a better-rounded manager. (PL)

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