Ever since I started playing fantasy baseball I have been involved in keeper leagues. My first league began in 1987 when I was a sophomore in high school: my friends and I started simulated leagues using Earl Weaver Baseball to play out our games. I maintain that Earl Weaver Baseball was light years ahead of its time, as you could input your own stats and customize your own ballparks. Rather than pick from the standard player pools as we all do these days, we picked our players from the Topps baseball cards that we had purchased that year. The only flaw in the game was its inability to handle extremely small sample sizes. For example, Carlos Garcia went 2-for-4 as a member of the 1990 Pittsburgh Pirates but I turned him into a pinch hitter extraordinaire as he safely got a hit fifty percent of the time I used him. The league flourished in my Computer Programming class during my sophomore year in 1988—despite the 5.25” floppy disk's confiscation one January following a Kent Hrbek homer around the Pesky Pole, an event that set off celebratory music  celebratory music in the lab.  

That league folded after graduation as each of us went our separate ways but I found another league in 1993 while working late nights at Burger King. The guy who worked the grill invited me to take over a vacant team in an NL-only league—the Barking Spiders franchise was mine. Once I got hooked into the standard 5×5 scoring league, I have never looked back. The only non-keeper leagues I play in are the two expert leagues I participate in each season. I love the challenge of keeper leagues because it adds multiple levels of complexity to the sport and keeps you in it year-round, even if your team is 55 points out in a particular season. I have seen success in keeper leagues for many years by following a few strategies that I have adhered to, and I’d like to pass the tips on to you that I learned from reading Sun Tzu and The Art of War. After all, the general who wins the battle makes many calculations in his temple before the battle is fought. The general who loses makes but few calculations beforehand.

Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat. This rule applies to reset leagues or keeper leagues, but failure to strategize will be felt for a few seasons if you do poorly on draft day. It does not matter whether this is the inaugural draft in your keeper league or the sixth one, you need to have a strategy and then stick with it. If it is your inaugural draft, you need to decide whether you want to field a competitive team right out of the gate—one that blends both youth and experience—or if you want to focus heavily on youth and build a team that is built for longer term success. A keeper league is a marathon, not a sprint, so there is no shame in falling into the second division in year one if you place in the money the following few seasons. Conversely, flags do fly forever so you can decide to draft the best team possible and play a boom or bust cycle like the Marlins did to win their two league titles in the real world. Either way, don’t let the draft dictate everything you do.

One defends when his strength is inadequate, he attacks when it is abundant. This is inflation at its core and it applies to both inaugural auctions and renewal auctions. For inaugural auctions, it has been my experience that owners forego traditional dollar values in the first two or three passes around the room and will overpay for the early names coming out, thus creating some values for those who play the waiting game. For renewal leagues, you will get a feel after the first ten or twelve tosses if the league owners have properly accounted for inflation and how to react to it. If you see your league overpaying for players, let them. Sheepishly take their ribbing about your roster being void of names, and then later sweep in and buy up all of the value in the next phase of the draft much to their chagrin. At the beginning of an auction, everyone is of the same $260 strength so the best time to execute the heart of your strategy is when you are higher on the money board. Track every bid and monitor inflation by the pick rather than waiting until the end of the round to recalculate. If you wait too long to do this, you will likely miss out on a developing trend rather than catching it before it peaks.

All warfare is based on deception. Whatever your strategy is, you must work your hardest to hide it from your competition as long as possible. You need to show an interest in every player that is thrown out and either help push the player’s price up or put on your best poker face while you look through your numbers to at least feign interest. If someone at the table picks up your tell that you do not care for the last two or three players that were thrown out with a certain skill or lack of a skill, they’ll confidently bid you up on a player they want later on knowing you have already shown disinterest in that particular player type.

Sun Tzu also tells us, “do not repeat the tactics which gained you one victory, but let your methods be regulated by the infinite variety of circumstances.” To best illustrate this, I will revert over to my 20 year fantasy football league. If you do not already know me, I am a long-suffering Redskins fan and I had one long-standing rule for my draft strategy–no Dallas Cowboys on my roster. For years, I would get up and leave the auction table when Aikman, Smith, and Irvin would come up as I would rather lose a fantasy title without Cowboys than win won with a Cowboy. I said, “had a rule,” because the first year Terrell Owens was with Dallas, I stunned the entire league by throwing out my only bid on him when I saw him $10 under my projected value and the shock value worked long enough for me to get the three count and win the bid.

To know your Enemy, you must become your Enemy. I find it helpful to lay out the rosters of all of my opponents before the auction and put myself in their shoes and make a plan of attack on how I would improve their team if I owned it. Are they light on power? Do they need to target steals, strikeouts, or saves? Once you figure out what each owner needs, exploit that knowledge against them within the auction. Each time it is my turn to toss the player nomination, I find the owner who has the most money left and then throw out the player that best addresses his biggest projected weakness. It will either force that owner to act and or exhibit another rule, “if your opponent is of choleric temperament, seek to irritate him.” You can get away with this strategy for most of the draft until you are in dollar days where you are forced to nominate players you want. Until then, force the action of your competition or let their inaction become their own undoing while you pursue the players you want as others nominate them.

And therefore those skilled in war bring the enemy to the field of battle and are not brought there by him. Dollar days are inevitable but you want to delay being in that position as long as possible. The earlier you allow your competition to drag you into dollar days, the worse off you are as you watch player after player you want go for $1 more than you had left to bid—and that includes some of the rookie building blocks you were hoping to target in the end game. If you are going to get into dollar days, save it for when you need a second catcher, a fifth outfielder, or a final pitcher. The last owners to dollar days control the end game as they fight from a position of strength rather than waiting for what is left on the draft board after the skilled drafters have dominated the end game.

Now, the reason the enlightened prince and the wise general conquer the enemy whenever they move and their achievements surpass those of ordinary men is foreknowledge. Simply put, there is no such thing as too much preparation for your auction. If you know what you need, if you know what your opponents need, you have properly calculated inflation, and you know exactly what is available in the draft, you have foreseen how the auction will play out as the Emperor did in the Star Wars movies. You need to have every team’s 40-man roster at your fingertips because those are the players that are likely to be recalled when someone on the 25 man roster is injured. You need to have Kevin Goldstein’s Top 101 list and his organizational rankings so you know who is next in line to replace players that are currently on the roster. It is alright to be caught off-guard by a roster move in a reset league, but in a keeper league, you cannot afford to be that reactionary. If you play in an ultra league format with 40-man rosters, the best way to ensure continued success on your team is acquiring tomorrow’s studs at today’s bargains. Opportunities multiply as they are seized. In order to stay ahead of your competition, you have to know who will hit transaction wire before the player hits the wire and a failure to not only be informed on auction day  as well as throughout the season will allow opportunities for you to reload your talent supply to pass you buy.

In summary, be Swift as the wind in your preparation, quiet as the forest so as to not tip your hand in the auction, conquer like the fire in executing your strategy, and steady as the mountain as you stick with your plan on auction day. When the owners gather at the end of every auction, there is always one team that everyone anoints as the team to beat because they had the best auction. Be that team, because the best victory is when the opponent surrenders of its own accord before there are any actual hostilities