Ask Rotoman: The Next Step to Winning

Hello,
I’m writing because I read your article in your magazine. It’s great it’s been around for 20 years.  Typically I print out a cheat sheet and try to study it and overstudy but can’t beat having a magazine with insights and tips.  I’m also writing because I am the commissioner of my league.  This will be the 10th anniversary of it!  It’s been 10 years and I still haven’t won a championship.  My league is with Yahoo 5×5 Head to Head.  I rack my brains out every year.  I’ve gotten better over the years, making the playoffs, but I can’t get over the hump.  Any suggestions or advice you may have, besides walking away with my sanity while it’s still intact?  I laugh buts it’s true.  Every year I try a different strategy but never seems to pan out.  Oh and it’s not a keeper league.  Which I think makes it a lot more difficult.  Thanks for reading my plea for help.  Hopefully I’ll be able to hear from you soon. Keep up the great work!
“Bridesmaid”

Dear B:
In my day (which is a long one) I’ve won a fair number of league titles, but I’ve been playing in Tout Wars for 20 years and not won a title. Second place a few times, in the money some, but never a first. So I know where you’re coming from. The fact is, however, that there is no one-size fits all answer to the question. Here’s why.
If everyone in your league was equally talented, equally smart, made an equal effort, in 10 years at least two teams, despite doing everything right, would not have won titles. In 2o years the odds would be that one or two equally talented teams would not have a title. So the fact is that we’re really looking at a sample size that’s too small to accurately judge what’s going on based on the results. The challenge for you is to analyze what’s happening in your league, and then come up with a strategy that will give you an edge, because the keys to winning are three: Knowing the values of players, knowing how other teams value players, and working hard to always get the edge in value.
Here are a few places to look:
Knowing the value of players: Of first importance is knowing your scoring system. How many points hitters and pitchers score, and when, makes a huge difference, and will determine how valuable players are. In shallow mixed leagues nearly all the value is found in the more better best most extraordinary players. While everyone knows these players, they’re the first ones to go in the draft. Then, at every pick later in the draft you’re going to have to choose between a player who is 30 years old, a solid regular with unspectacular production and a player who is younger, more athletic, but with perhaps injury or playing time issues. In other words, $10 in the bank versus the possibility of buying $20 with the risk of getting only $1. What you need to remember is that in a shallow mixed league the value of $10 in the bank is less than the riskier player, because if your riskier pick fails there will be other players available on waivers who are almost as good as the safe pick.
Knowing how other teams value players: One of the things I like about drafts is that bad players can totally screw up picks if they don’t know how the room values players. One of the things I don’t like about drafts is that I can screw up picks, too, if I don’t get the room right. The way to get familiar with what other people do in the draft room is to participate in Mock Drafts. It only takes a few, played by your league’s rules, to get a feel for the types of players taking Adelberto Mondesi and Vlad Jr. in the second or third round. There is variation in every mock, but seeing the highs and lows for players will give you an idea about when you need to reach for the guys you value highly, and not reach too early. (It’s also an opportunity to try out different approaches to your draft, to see how the opposition reacts.)
Working hard to always get the edge in value: Working harder means working effectively. I think your first order of business should be to figure out if there is a reason other teams have won your league. If it’s just one or two guys winning, what are they doing? If it’s a different team winning every year, and they’re all doing different things, what are all the things they’re doing? And what can you do to find the bargains they leave behind. Then, work hard in season to stay on top of matchups, player health and slumps, and pursuing creative trades that can earn you extra points bit by bit. Extra points lead to extra wins.
You may or may not solve this thing this year. Head to Head can get pretty random, especially in the playoffs, so the best team doesn’t always win. But having the best team will give you the best chance. If you execute this year and honestly evaluate after the season about what went right and what went wrong, you’ll be able to hone your approach the following year so that you get better. Consistently working in a framework of evaluation and experimentation is the way to improve, so that when you get lucky you’ll find the championship you long for.
Good luck!

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