Oh man, quite a few replies again, so forgive me if some of my answers may be redundant
I appreciate the apology Casperian, thanks.
I´m glad we got that out of the way.
Your offer is a bad one and the idea that if I don't take it I'm "Chicken" or something is straight out of Back to the Future. I'm not Marty McFly and you're not proving your point via that.
Yes, it was not a fair offer, we both agree on that. To be honest, I did not expect you to take the offer, anyway. You´re too smart for that.

In particular your wager is a poor one as the C's at the maximum are going to have a 16% chance to win. To make the bet "fair" you'd need to be offering 6 to 1 odds.
That´s besides the point. To take my offer, all you had to do was to tell me which record will eventually win the lottery. We both agree that this is not possible.
Its clear you don't believe in expected value. If you think its snake oil that's your prerogative. But just because there is uncertainty in what lottery combination will be chosen doesn't mean that every team shouldn't desire to have the most combinations on their side.
...at what cost?
If you were just saying like Nick that we shouldn't tank for other roster reasons I get that it makes sense to me. I agree that purposeful losing is very destructive.
Yes, expected value is clearly not accounting for a full year of life you, me and everyone else has to live
while we increase our odds (marginally), or as nick puts it, the human element. The relation between investment/return on any attempt to game the system alone is not worth the price we pay in attrition, in my opinion (even if that´s only mental capacity for some of us).
As I tried to showcase with my answer to the crude box example, and since we both agree that knowing the future is impossible, why waste time and energy on rooting for losses? How will you guys feel if we barely edge out the Lakers in the "tank rankings", only to see them leapfrog us in the lottery? If somebody says "we did the best we could, it just didn´t work out" afterwards, well, that might very well simply be revisionist justification of his beliefs. In other words, a mental circlejerk.
You did, however, say (paraphrasing): "Yes, I know the best position to be in, and it´s the one with the most combinations". After reading your follow-up posts, it should be clear to both of us that this particular statement of yours was not true.
I guess what we´re really arguing about here is a matter of priorities. And the problem I had with your wording was that if people take this at face value, it will mess with exactly those.
But the argument that because its a single random event that every lottery slot is equally unappealing/appealing because the winner is unknown doesn't make any sense to me.
Not every lottery slot is made equal, I agree on that, but mainly because of the potential floor, not ceiling.
You said yourself, we don´t know the future, all we can do is to try our best. Try our best at what? Many argue for probability (more losses), I prefer things like Stevens´ coaching ability, for example, or Adams´ coaching ability, or Danny´s ability to evaluate talent, or the owners willingness to put money into the team. Trying our best at something that will most likely not yield expected results is futile. Wasted energy. Steadfast belief in probability is (at least to me) in and of itself not a convincing argument for a certain direction, either. Not at this point in time, at least.
According to the math, every fourth lottery should see the worst record win it all. Out of 1000 lotteries, 250 should see the worst record win it all. 5 of them should see the best record win it all. The thing is, nobody knows at which point in the circle the 2014 lottery will fall.
Now, if we planned to be in several draft lotteries, my stance might change. That´s because each consecutive event after the first one basically substitutes as a fail-safe in case the first one didn´t work out, and that´s when probability gains traction as a viable argument, but then again, which fan in their right mind wants to be in several lotteries?
To get back to your poker argument a few pages back: even the most successful poker players have stories about that time in their life when they couldn´t win a single pot. Did they lose their ability to play? Did probability stop working? Or did probability work exactly how it was supposed to work, and they just had to suffer through a dry spell? Most importantly, does it matter to the landlord they owed the rent?
As for the box and ball bet discussed, it has no relevance. You can't really apply that analogy, as the 'negative result' has a disproportionate outcome to the 'positive result'. There's no probability or expected value in the world that would sway me to take that bet. That isn't even remotely the case in the NBA draft lottery. You don't lose your team if you 'lose' the draft lottery, you just get a less nice 'house', or whatever.
I´d say to lose a whole year and suffer through witnessing fellow Celtic fans root for losses, only to get Marcus Smart, is pretty much the definition of a disproportionate negative result, but of course, that´s entirely subjective. Either way, I would not want to be the one who "smartly" gamed his way out of Wiggins and into Smart.
Wouldn't this logic mean that the entire weighted draw system is an illusion? That's just a probabilistic setup for a one-off event, after all. Or are you saying the probability is real, it's just that anyone subject to it should deliberately ignore it in a one-off event?
The third alternative. Probability is real, but any NBA team subject to it should deliberately focus on other things in a one-off event.
EDIT: And, of course, teams do have 100% certainty of a range of picks. The worst record will never pick lower than 4th, 2nd worst 5th, etc, etc. When you look across multiple picks rather than just #1, teams with worse records have a much clearer advantage.
Yes, that is, in my opinion, the only reason why losing games can be worth it. However, we´re pretty much out of a surefire top 4 pick. Anyway, trying to game the spread at this point in time is relatively meaningless compared to other important factors, like Danny´s ability to evaluate talent, and of those who pick ahead of us, for example.
First off, I think you've misunderstood the statement, and given Faf's post (and everyone else after it), it seems you're the only one who did. Let me try clarify.
I take it that when I said "best position", you interpreted that as "having this record or rank in the lottery will yield us the best result, which is winning the lottery." That couldn't be further from the truth.
Okay, forgive me for being captious, it´s been a long season. You have a TP, too.
If so, then take up my offer, which is I bet you a TP that neither of the Suns/Mavs/Griz will end up with a top 3 pick. Another TP that the C's will end up picking higher than whoever of those 3 ends up 9th in the west.
The Suns/Mavs/Griz can win the lottery, and they may very well end up with a top 3 pick, but I'm playing the odds here. There's approx. a 1.8% chance that I lose 2 TP's, and a 98.2% chance that I win. But since this is one of those one-off events, do you really care about such odds? 
Ha, you got me there, eh? Alright, it´s on.
Maybe I should acknowledge that there´s a certain threshold, at which point gaming the system would make sense? Anyway, that threshold is certainly higher than 25% and thus not really applicable to the lottery.