The Art of War — Managing Your Roster

“Move swift as the Wind and closely-formed as the Wood. Attack like the Fire and be still as the Mountain.” — Sun Tzu, The Art of War

Asking for fantasy advice can be a frustrating experience. In few industries (lookin’ at you, Donald) can a simple either-or question, be answered in a million different ways, each with unique caveats and considerations . Even more frustrating is that all answers can still be right! Fantasy “experts” (I’m guilty of this as well, despite my lack of expertise) will contradict their own rankings or their own strategy articles when advising on team-specific questions, and wrap all responses in the “process over outcome” wrapper.

This is not an indictment on any fantasy sports writers or on the fantasy industry as a whole. This is a necessary evil in a competitive activity dealing with projecting the future and overcoming variance. This Art of War quote gives us an excellent first step into decomposing this seemingly contradictory advice. It takes what could be misconstrued as opposing styles, and wraps it all together to highlight the dynamic nature required of a victorious leader. Let’s break each of these 4 pieces down into greater detail, as I force a fantasy sports metaphor into each quip. Each of these four sections will outline key parts to a successful fantasy strategy, and I’ll talk about how each one of these paradigms can result in contradictory fantasy advice.

Move swift as the Wind = Stay on the Waiver Wire

Regardless of sport, being the first to check who cleared waivers is a huge advantage in hyper-competitive leagues. The impact is larger in weekly transaction leagues because it allows you to gamble with your waiver priorities and preserve a higher priority position for subsequent weeks. Streaming defenses in fantasy football is a prime example. Streaming defenses is a well-recognized strategy, and typically practiced by multiple owners in all of my leagues. On Wednesday morning, when waivers clear, at least 2 or 3 waiver claims are spent on a middling defense going up against a poor offense in the upcoming week. The reality is, I find myself picking between more interesting waiver wire defenses then there are potential suitors for the same player. I may have 3 or 4 defenses I’d be happy streaming, and know full well that only 2 or 3 will get claimed off waivers. If I’m in the habit of checking first thing Wednesday morning, I can be just as happy cleaning up the scraps and keeping my waiver claim and improving my priority for the next week where an injury to an RB or WR may present a more interesting use of the claim. Stay on top of all waiver wire happenings, and be ready to pounce on any players who slip through the cracks.

Closely-formed as the Wood = Only Fill Your Needs

On the flip side of hoarding the waiver wire, comes the restraint to only claim what you truly need. Be picky with how you manipulate your roster and be sure to not create any roster gaps by being the first to own a player. In almost every format, roster space is limited and the manager who can maximize each roster slot is going to be in the best position to win. If you’ve drafted Corey Seager in the 1st Round to be your SS, don’t trip all over yourself to be the first to grab J.P. Crawford or Brendan Rodgers. It’s nice to have the newest, flashy toy, but even if everything breaks right and the prospects succeed right away they won’t start on your team. Have a plan for every player you add to your team, and don’t just blindly add any player listed on the top of an expert’s weekly waiver wire article. Every roster, in every league is a unique puzzle and very few generic articles apply across the board to every manager.

Attack like the Fire = Focus on BIG Trades

The quickest way to improve your standing in the league is to make a positive trade in your favor. A winning trade improves the quality of your team, while diminishing the quality of an opponent. The difficulty comes in finding a winning trade. Assuming competency and fairness in the opposing managers, no manager is willingly going to make a trade that does not favor him/her. Odds are each owner is going to be right roughly 50% of the time, and wrong the other 50%. So we have two main options for trading: 1) find an owner with misaligned incentives. This really only works in dynasty leagues, or in re-draft leagues where there is a significant penalty for losing the league. If a manager is looking to win in future years, they may sacrifice value in the present. 2) Go All-In on one or two trades. The managers who make a ton of trades, typically end up in the middle of the standings. That’s because they won big on a few trades, lost big on a few trades, and many that came out in the wash. So my advice would be to make one big bet, and hope it pays off. Whether you over-leverage on a certain strategy (i.e. target all 5 pitching categories and SBs in 5x5 H2H league) or you make a play for a boom-or-bust type talent and hope to catch a hot streak (i.e. a trade for Gronkowski after his first 11 injury-riddled weeks of 2016). To be clear, I’m not advocating for trying to pull a fast one on any opposing managers. I hate the guy who sends non-stop, ridiculous trade offers as much as you do. What I’m proposing is to make one big play, and bet the season on a well-reasoned strategy. Like card-counters at Blackjack increasing their bet size when the count is in their favor, there’s no guarantee the next hand will work in their favor, but they’re betting big and willing to take a risk to make a big swing in their results.

Be still as the Mountain = No panicky, BIG moves

While risky plays can catapult your team to a championship, trades completed out of early panic will often leave you burned. Practice patience and let regression run it’s course before making any major moves. Be still as the mountain and survey the entire landscape before making your attack. Waiting until the trade deadline allows you to gather as much information as possible, while also increasing the likelihood of finding a trade partner desperate to take a big risk. This “attack like fire” and “still as the mountain” contradiction is why asking for trade advice can yield such different responses. Many experts correctly advocate that you should always receive the best player in any trade — take quality over quantity. They’ll also encourage you to not make any big trades early in the season as indicators of future success continue to stabilize (BABIP, # of targets, etc.). One trade could receive “don’t do it” advice early in the season, while receiving a “this is a no-brainer” mid-season based on what their ROS projections look like, and what your position in the standings are. Be on the lookout for a BIG move that could swing your season to extremes, but don’t force the trade to happen until the moment is right. Be still, and patient and attack with fire when all the stars have aligned.

The culmination of these four tidbits, is the foundation for fantasy success in any sport, and in any format. Interesting little wrinkles will exist depending on format, and I’m happy to discuss those in detail via email ( or via Twitter (Brian Creagh). I appreciate any feedback, and encourage everyone to reach out with questions or recommendations for future content.

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