Keeper league strategy: Winning

Sorry for not posting yesterday. It was the trade deadline in a couple of my leagues, and I was working the phones. As per my own advice, I had completed the majority of my trades a few weeks ago and laid the groundwork with the owners who made the mistake of wanting to wait to trade. Those were the owners I was working with yesterday (over the past few days, really). In the words of my favorite Kazakh reporter, “Great success!”

First, a quick note. I had originally planned this as one article, but since it ran longer than expected, I’m going to break it up into three. Expect the remaining articles in the series shortly!

Keeper leagues

Most of this year, my writings have been dedicated to redraft leagues. I’ve rarely talked about keeper leagues, despite their growing role in the world of fantasy baseball. This might be because of the varying rules in keeper leagues. It would be difficult to find two leagues with exactly the same setup, so giving generalized advice can be difficult.

Many readers that are in keeper leagues have been in regular contact with me for advice, but I’ve never written up a formal post about them. I know that some trade deadlines have passed, but in other leagues there is still time. If you’re in a keeper league and are playing for next year, listen up, even if your deadline has passed.

Rule #1: Always play to win

If you’re sitting in fifth place right now and are confident you can come in second or third by making a couple of trades… don’t. Unless you’re in an ultra high-stakes league where you can make a small fortune by coming in third place, don’t play for it. Always play for first. Whether that first comes this year or next is up to you, but never fall into the trap of settling for less. If you don’t think you can win, go into ‘next year’ mode.

I can’t speak for everyone, but I know, for myself, that second place is simply not satisfying. Second place, in anything, feels the same as last. I always go 100% at everything I do and settle for nothing but first. I care more about the win than the money. Of course, some of you probably are the opposite, valuing money more than the win. Whatever your top priority, playing for less than first is a mistake.

In our example from above, going from fifth to second might require you to trade a player who would be valuable next year. Avoid this temptation. The big money — and the glory — come from first place. Be patient. Would you rather come in third twice or first once and fifth once? And since you’re aiming for that first to come next year, it becomes even more likely that you’ll be able to take first in the years that follow. If you’re continually playing for third, hoping for some luck to allow you to take first, it will be difficult to break that cycle of mediocrity.

Set yourself up really well for next year, and the chips will fall into place from there. The next couple of articles will explain some not-so-obvious ways to do this.


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