If the positon of his 2nd pick doesn't change and the act of not making a first pick does not effect the decision of the other teams, then the math is not changed. After each successive pick, his odds of getting 2 players does improve but it does not affect the overall odds of getting 2 players.
I don't follow. This seems like a contradictory statement. With each successive pick, if all four of his targetted players remain on the board, his odds increase. Like I said, I think this really came down to the fact that the other owners simply did not value the players the same way he did and therefore the players were still there. I think this says more about his player valuations thatn it does the strategy.
His odds do not increase at all. In fact, I would argue that his odds of getting the players he wants actually decrease when he waits.Let's look at a simpler case to make it clear. Let's say you're drafting in the 1.11 slot in a 12-team league. You really like Jamal Lewis and Tiki Barber, and you want to get them both. In the normal case, you select one of them and hope that the guy at the turn doesn't take the other; the probability that Barber is still there at 2.02 is the inverse of the probability that the 1.12/2.01 drafter (Team B) takes Barber.
So what if you decide to wait on your pick. Now Team B can take
either Lewis or Barber. If he takes either one, you lose. So your probability of getting both is now the inverse of the probability that Team B takes
either Barber or Lewis. It is trivial that this probability cannot be lower than the probability that Team B takes Barber, and furthermore, it can be shown that your probability of getting both is actually lower if you use this tactic.
Suppose Team B's draft board looks like this:
Lewis
Kevin Jones
Dillon
Barber
In this scenario, if you take Lewis with the 1.11 pick, Barber will be there with the 2.02 pick. But if you pass your pick, Team B will take Lewis with 1.12; you just screwed yourself, for no potential benefit.
This result is generalizable; you never improve the probability that one of a group of players will fall to your next pick by passing your pick. You actually reduce the probability, because you give your opponents the chance to select a player who may be higher on their draft boards, that you should have taken with your own pick.