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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

Thank you for reading

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briankopec
3/08
Earl Weaver Baseball...oh the hours we spent on my Amiga replaying the 1989 season.
moonlightj
3/08
IBM PC here....luckily I was an avid fan of backing up so I had archive copies of my EWB disc when the first one was confiscated. I've tried to play the simulators online but it just isn't the same for me.
briankopec
3/08
Emulating it on my PC works really well. Go find an Amiga emulator and give it a shot (WinUAE).
moonlightj
3/08
Please email me with some details/advice....I have the itch again :)
briankopec
3/08
Will do when I get home.
everettcase
3/08
I'm also a long-suffering Redskins fan who "would rather lose a fantasy title without Cowboys than win won with a Cowboy"... haven't broken that rule yet but I almost did for Felix Jones this past season.
bjfrankfort
3/08
Jason-
I am going into the auction with a significant advantage in available $$ (about $20). It is an NL-only, standard 5x5 league, 7 keepers per team. There is a lot of talent available. Since my advantage is very great at the outset, would you recommend targeting the player I most want and simply acquiring him up front?
moonlightj
3/08
If you have the significant advantage money wise, go get the 1-2 players from the pool you want that are integral to your strategy. You control the draft from the get go. If someone is going to drive you up on that player's price because they know you want him - stick that owner with that player and make them adjust your draft.

A lot of people say they want to price enforce but I doubt they have a plan in place if someone calls their bluff. I'd throw that player out at 90% of your projected value and go from there to get a read on who is serious and who will bow out quickly.
DDriesen
3/08
You have learned well, Grasshopper...
flalaw
3/08
One strategy I cannot recommend enough from nearly 25 years of auction drafting in keeper leagues is to remember that your goal is to maximize the value of your team, not just to maximize profit.

Gauging inflation, both pre-draft, and in-draft, in the most important thing you can do assuming your valuations are sound. And the first key moment in this is to project who the other teams in your league are going to keep, and then calculate inflation. If inflation is significant enough (say 15% or more), you may want to consider keeping reliable at-value or slightly above value keepers in order to 1) add value to your roster and 2) go into the draft with fewer $ that will be eaten by inflation. And inflation WILL be allocated to the top-tier players.

So if you have a $35 player at $40, keep him, especially if your league allows a large or "unlimited" number of keepers. If you don't have one of these players, try and trade for him if you think the other owner won't keep him (he'll probably want little in return since he doesn't view him as a keeper). In a high-inflation draft, the best bet is to lock in as much value as you can and go into the draft with as little money to spend and few spots as possible to fill; if you go in with $200 to spend, you WILL feel the effect of inflation.

The worst thing you can do and surest path to a low-value team is to be one of the guys sitting on too much money after the top-tier players go, and ending up paying $32 for a $17 player. I've seen it happen too many times to too many teams.
moonlightj
3/08
For years, I always bought the first player in my keeper drafts because I found that everyone either miscalculated inflation or didn't do it at all. This is particularly handy if you're in a league where you're changing the amount of teams in the league.

chabels
3/08
I've found this to be true in my 15+ year keeper league as well, particularly for the first 'non-stud' player. In my league (AL & NL East + DET, CIN [thanks for the PFM change that allows this]) everyone knows that Teixeira and Sabathia are $45-$55 players. But nobody really knows what Max Scherzer or Mark Reynolds is worth until similar players have been priced. It's the mid-tier player, the $20-$30 guys who are the most frequently under- and over-paid.

That said, because of our long history, there are only two or three first starters and two or three 30HR+ guys available in the draft, and if you need one, you've got to pay for it.

I love the idea of filling my roster with a bunch of $20 guys rather than a $40 and a $1 guy, but in practice, only half the $20 guys deliver $20 production, and barring injury (thanks Carlos Beltran) it's rare a $40 player doesn't generate at least $35 in value.

Lastly, those $40 guys are the trade chips to have if things go poorly and it's time to play for next year. Edwin Encarnacion might be a modest upgrade for someone with Placido Polanco, but you're not going to get that much back, where Longoria is an upgrade for just about everyone.
eighteen
3/08
Two traps in every auction. One, being the richest man in the graveyard. Two, confusing cost with value (i.e. $1 for some players is too much).
shmooville
3/08
I couldn't agree more with One Flap Down above. Over the years I've found my primary weakness in auction formats in keeper leagues was to let everyone else overpay for top tier talent, and then wind up with too much money at the end. Some negatives are to eventually wind up with the players you wanted but at lower prices than you expected, because you underestimated the aggressiveness factor of the rest of the league in pricing the Tiers of talent. One point that I would contest with your basic assumptions above Jason, is that I've tended to find in my keeper league auctions that often the best fair value top tier players actually go early in the draft and only sometimes do you get bargains late. This is because of the classic laws of supply and demand. Thus, if your strategy relies on a top 5 or 4 type of player, to use Marc's representation, then I would suggest targeting your player early before other players at the same position fall off the board. Stricter adherence to value propositions are better for the middle to lower tiers. Does anyone find this not to be the case?
moonlightj
3/08
"One point that I would contest with your basic assumptions above Jason, is that I've tended to find in my keeper league auctions that often the best fair value top tier players actually go early in the draft and only sometimes do you get bargains late. This is because of the classic laws of supply and demand"

Fair points -- I am looking at values early and late in the draft. If you can control the end game with your last $20 at a draft table, you're in better shape than the guy who has $7 for 5 players. There is a balance there between spending too early and too late, but that comes with monitoring inflation pick by pick.
Ecrazy
3/08
"Some negatives are to eventually wind up with the players you wanted "

There's your problem right there. You shouldn't "want" any players at all. You should adjust prices ahead of time to reflect how much you "want" them. That way a deal is a deal, regardless of the name attached to it. Wanting players is the surest way to lose.


There are TWO universal truths in an Auction:

***When the first player of the auction is purchased, 12 other owners thought he was overpaid ***

***When the last player is bought, it doesn't matter what the other 12 owners think***

The trick to doing well, is finding that middle ground, where you stop bidding against every owner , and just bid against a few. It's this sweet spot that wins the day.
varmintito
3/08
I'm not in a keeper, but shmooville's advice is sound in a redraft auction as well.
There are no bargains for top tier players, only differences in valuation. If anything, the price of the last 1-2 superstars at a position can be far higher than a comparable player nominated earlier, especially where there is a steep drop off.
Value time is when most of the superstars are off the board and some owners are acutely aware that they have $57 left to spend on 14 players.
The beauty of an auction is that it rewards good planning AND the ability to adjust.
Pinson
3/08
I don't get it. The article is supposedly about auctions, but Paragraph 3 is all about drafts. Of what use is the article if the author can't distinguish between auctions and drafts?
moonlightj
3/08
Draft and auction, as used in the paragraph, are events rather than describing the type of event. My mixing of the terms was likely due to fielding the multiple when/where is "the draft" questions in the 3 leagues that I run so my apologies for that confusion. The advice, however, would apply to either format.
beitvash
3/08
It's about innagural auction drafts, for keeper auction leagues who are starting at "Year 0." There is a different strategy for leagues in this state.
wennodc
3/09
The Barking Spiders has been my team name since 1996 too--small world, eh?
moonlightj
3/09
I have no idea where it originated from -- I just inherited the team name. That's too funny.

I keep my team names as long as I win the league. Personal DeJesus has been retired in 2 leagues and has been replaced with I Like My Women Buehrle Legal with Chris Hanson as the team logo.
aliendna
3/09
What exactly is inflation? Is this overpaying the traditional dollar values by position? My keeper league typically pays a 10-20% premium for starters but always underpays for catchers. Are you then suggesting going to battle with a two-edged sword: “I am looking at values early and late in the draft” as well as “If you have the significant advantage money wise, go get the 1-2 players from the pool you want that are integral to your strategy.” So in other words, it may be necessary to overpay for a few key players but primarily focus on value?
BurrRutledge
3/09
Inflation refers to the value of your auction dollar as the auction progresses. If you track how much is being spent (as the PFM will help you do), you can see how much money is left for the remaining talent. So, if some of the top players each were claimed for a few dollars less than expected, then the dollar value of the remaining players is determined in relation to how much money is left out amongst the bidders. Therefore, there price tag actually goes up compared to what you might have expected.
moonlightj
3/09
Yes, you need to show some flexibility with the stars in the league. Inflation assumes that everyone will stick by the book but if 1 or 2 players in the league go stars and scrubs, someone could end up exceeding the inflation price of the player.

Last season, I had a very loaded offense in my keeper league along with cheap relievers. I needed five pitching spots and had budgeted $90 for my remaining pitching. I missed my auction because I was doing Tout Wars but I told my proxy to get Hamels and Halladay on my team. I had projected Halladay with a $43 inflated value - he went $50. I had Hamels projected at $27 and he went $33. I had the high money going into the draft and those 2 were the 2 of the first 4 names thrown out. I got what I wanted, but had to pay a little more, but it also screwed up the draft plans for others who thought those guys would be attainable.
Robotey
3/09
For every experienced veteran GM in a keeper league there is no recurring nightmare like the "I have $80 left and 8 spots to fill and a pitcher named Snell is the best on the board". I lived that one year and paid $24 for him and clearly I have not gotten over it. Better to overpay 3 or even 5 dollars for a player you love--Hanley, Albert, Utley etc.-- than curse yourself later. You'll more than likely bid $2 instead of $5 on a 5th starter later in the draft and at that point it's a toss-up. The simplest way to prepare for the draft is plug in your keepers and then plug in your dream roster with real prices. Once you start doing that you'll realize you've only got a buck apiece for your last OF --or maybe last two, same for last starter --or maybe two, and your last RP and Utility, mid etc.If you know what your roster will look like having over-budgeted for your favorites then you'll be able to deal with it later in the draft. Last year Halladay snuck through early in our 11 team NL keeper for only $28 and we all kicked ourselves all year over it. Just because I had Hanson, Nolasco and Lincecum was no reason for me to let him go that low. If you get the half dozen players you want--you may need a plan B in some instances, Uggla for Utley etc. -- then you won't walk away from the draft with the woulda coulda shoulda's.
VDracul
3/11
Art of War is on my bookshelf and reading this article, makes me want to go read it. Maybe I will dress up like a general for my draft day and only answer to "La Commandante".
Victory shall be mine!