There’s an old saying that “generals always fight the last war.” The origin of the saying is unclear, but the idea behind it is not. During their current engagements, people tend to do the things that has worked well and avoid the things that didn’t work well during their previous engagement, rather than choose their course of action based on the current circumstances. And it’s not limited to war—a variation on the statement insists that “economists always fight the last depression.”

In my deep AL-only league keeper league, I’ve had the same issue the past few times I’ve had a contending team. I didn’t trade away my prospects and/or cheep keepers to the teams that dumped early because I didn’t like the prices I was paying. Each time, I felt like the contenders who made those deals overpaid and that I would overtake them when I made subsequent deals at better exchange rates. Each time, I was wrong.

A few things caused problems for me in these scenarios:

• There’s no guarantee that any other teams will dump. Sometimes there is no “next” deal to make.

• There’s no guarantee that teams that end up dumping have assets as good as the ones the first dumpers offer.

• There’s no guarantee the later dumpers won’t hold out for the same exchange rate that the early dumpers got, even to their own disadvantage.

• The earlier a contending team acquires assets, the more stats the contending team gets from those assets.

This past week, two different teams in this league announced that they were dumping and had their eyes on 2018 and beyond. I am one of 5-6 teams in contention this year and I wanted to make a big deal with at least one of these teams. I had the cheap major leaguers and the minor leaguers required to make a significant move, or maybe even two. I even mapped out a scenario in which I made big deals with both owners.

Sunday evening around 9:00, about three hours before the weekly transaction deadline, I finalized the bigger of the two deals. I felt like I overpaid slightly, but I knew that I’d be sunk if I didn’t get a deal done, because this owner had the only ace available and I needed an ace. It’s the kind of move I haven’t made in seasons past, seasons in which I finished somewhere between third and sixth and still had assets for the future on my roster which I could have used for more immediate returns.

As soon as that deal was finalized, I sent a follow-up offer to the other dumping owner to try and get his best trade chips, too. I offered a cheap position player and two of my four minor leaguers based on preferences I had him define earlier in the week. He turned it down, saying that he was in talks with another owner and wanted to wait one more transaction period. I wanted to beat the other owner to the punch, and I also wanted to avoid having two injury-based dead spots in my lineup for the upcoming week, so I added a third minor leaguer to the offer, again based on this owner’s stated preferences. He accepted it, prompting several fist-pumps from me—despite thinking that I was overpaying, based on long-term asset-exchange rates in this league.

While the argument could be made that I overpaid a bit in each deal, I am happy with both deals, especially in concert with each other. Two dumping teams already have shed their best assets. The fact that I got those assets in each case is obviously good for me, but the fact that there are now fewer assets to be acquired by the remaining contenders helps me quite a bit, as well. The remaining contenders will have to outbid each other for the remaining trade assets, driving those prices up. And each of those contending teams will be hard-pressed to acquire the best trade assets from multiple dumping teams.

So, yes, part of my motivation in making these deals was to avoid making a mistake I had made I the past. However, I don’t think I’m fighting the last war here despite the nagging voice in my head telling me that I am. I think I identified a weakness of mine that had been a problem across multiple seasons, not a specific concern associated with a single case. I think that I’m less like a general fighting the last war and more like a hitter who just closed a hole in his swing. I hope so, anyway.

Thank you for reading

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This is exactly my problem - thanks for writing this. Three teams dumped a month ago (and the same owner got nearly all the stud assets - Goldy, Pollock, Darvish, Cano), and I had a really comfortable lead. Then I started getting slammed by the injury bug, and now there aren't enough stud expiring contracts to go around, and closer prices are through the roof. I should have made at least one move to block him, but this owner is so aggressive that I should have known I needed to account for him.
I've been there, man.
I wish you hadn't written this. :-)

Excellent article and I agree wholeheartedly. I've operated in this manner for years to my definite advantage since most of my league mates do not. They hem, haw and are reluctant to overpay, especially early.

I end up getting extra months of production while they sit and hope better players come along. Maybe they do. Maybe they can get them without overpaying. But they still have a weakness on their roster for longer than I - and nothing stops me from trying to block them later when new dumping teams show up. Maybe a 6th or 7th OF will just sit on my bench. But injuries happen to my team and, again, my competitors still have a hole.

Flags fly forever and dynasties are hard to build in keeper leagues with limited keepers and contracts that will expire. You have to make the moves that give you the best chance for now and worry about next year at that time.
Well said. Good luck.