In the America’s Cup in 1983, Dennis Conner committed a fatal blunder, based on his failure to use a “follow the leader” strategy, leading to the first loss by America in that event. Essentially, the basic strategy in sailboat racing when you are the leader is to follow whatever the trailing boat does. In this way the trailing boat can never gain on you; if he has the wind you will also, if he doesn’t well neither will you, but he still cannot gain. This is a dominant strategy in game theory parlance. In that event, Conner had a 3-1 lead and in what should have been the final race, he kept his boat to the right of the course. The opposing captain, hoping to get lucky by gambling on a wind shift, sailed to the left. The rest is history.

I always thought this was a fascinating story and a good lesson to any strategist. When you have a dominant strategy or a simple strategy that will work, then you are making a blunder in failing to use it. If you have a dominant strategy you never lose by using it if you are in the lead; gambling can only make your situation worse. This is true at least when there are two competitors; when there are three it is much dicier.

What does this mean to the Fantasy General? In my high stakes league, I have a relatively large lead. The only close competitor, right now at least, made a huge trade proposal: he would trade Chase Utley, John Broxton, Jacque Jones, Brandon Inge and Evan Longoria and would get Michael Cuddyer, Kevin Youkilis, Trot Nixon, Eric Byrnes, Marcus Giles and Brad Hennessey.

I had two options; option A is to sit tight, make a smaller deal for an NL closer (I just lost Salomon Torres and needed the saves) and hope for the best. My current point total was 285 and his was 240. This was a fairly large lead, the usually winning margin in this type of league is between 10-20 points. So there was the possibility, a la Dennis Conner, that I could not respond, sit back and hope that a small move would let me hold on to the lead.

Option B is to aggressively try to knock this deal off the clock. I can not only perhaps make a deal that improves my position, but can also achieve the double whammy of preventing my close competitor from making a deal that would give him at least a fighting chance to catch up, which he may have anyway if my team falls back to the pack.

Looking at it in terms of points, it appeared clear to me that option B was my preferred strategy. The deal clearly, in my estimation, would put him in at least the 260 point range. I will spare you the details of my calculations. While I have 285 points now, with the loss of Torres, a failure to bounce back by my young hitters (see below in my post on the Arizona players) and a fall back in my AL offense, it was clear that option A, though it would preserve future value since I had to trade some very keepable players, could very well be very costly. I thought that if I lose to him so be it, but it will not be because of a Dennis Conner type error!

So I ended up trading BJ Upton, at a very keepable $10 salary. In this league, you can contract a players for long term deals after two years by increasing his salary by $5 for each year. So, most likely, I am giving up three years more of profit on Upton. The entire deal:

BJ Upton, Nick Punto, Zack Greinke (at a $1 salary) and Taylor Tankersley at $5; for
Brad Lidge, Brad Hennessey, Craig Hansen (at $2) and Michael Cuddyer.

Why this deal?? I am selling high on Upton; if he falls off as his xBA indicates he should, and Cuddyer continues his current performance, then aside from steals (of which I have a lot anyway) I might even gain offensive points, but at a minimum I hope to not lose too badly. With Lidge and Hennessey, I felt that if I were going to make a “make or break” trade then I had to get two iffy closers if I could not get one excellent one.

This was a clear attempt to minimize the risk; both have the skills to keep a closer’s job, and if they both pan out I can dump one and can keep Hennessey next year (Lidge is not keepable), thereby at least lessening the future damage. At a minimum I would expect at least one of them to hold the job for the rest of the year.