Specific Scenario:

Final Table of a big tournament. You are chip leader with nearly 50% of the chips in play of a 5 handed table.

Short stack with 20bbs shoves UTG with say A10o.

Everyone folds to Chip Leader with 100bbs who contemplates with 55 in sb (other short stack is in bb). Other players have 20bbs, 30bbs and 35bbs.

Payouts are roughly 1st 2 million. 2nd 1.3 million 3. 800k 4. 500k 5. 300k

Should you always be taking what is a essentially 200k flip or be finding better spots to exploit? Are there any reasons NOT to take the flip?

What did the ICM calculator say when you asked it?

dont have one...and have never used one.

Without factoring in specific ICM calculations, you'll still have at least double the amount of chips of every player left even if you lose the flip... I would go for the bust.

I recommend googling ICM and looking at ICM calculators. They are specifically for answering exactly this kind of question.

The short answer is, it depends. When you get close to the money, you start looking at the $EV of situations along with the Chip EV. Early in a tournament these are about the same, but as you get close to the money there are discontinuities and exaggerations.

Just fold it.

You want to keep pressure on all players and doubling up the 20bb stack removes it slightly because then 3 other players have decent stacks to play with. Two short stacks will both feel desperate, and taking the big blind from you won't alleviate that. Keep them forcing to open large wide and call narrow because it creates a favorable table dynamic for your big stack

In theory, you should reject some marginal bets because chips you win are less valuable than chips you lose. However, ICM considerations will rarely matter more than a couple of percent, and here you have a 53% to 54% edge (depending on the suits) and you can win 21.5 by risking 20 (you don't mention antes).

In real poker, I fold this. The problem is you can't have much more than a 54% edge unless the guy is playing 42o or something else silly (okay, he could have A5, but it's not likely), and you might be 19% versus a higher pair, even a pair of 6's. You are looking for the opposite, situations in which you cannot be a big underdog, and might be a big favorite.

One other general piece of advice. Concentrating on stack sizes leads to passive and predictable poker. Most people are better off playing their tournament A-game and in close calls choosing the more aggressive action (raise or fold, don't call), concentrating on the other players and the table feel, and letting the chips fall where they may.