From Wikipedia
Negative freeroll is a term used in poker. It refers to a situation, usually occurring in no-limit or pot-limit when contemplating an all-in wager, where the player acting first checks in a situation where they would be forced to call an opponent's final bet (due to pot odds and the strength of their holding). If the opponent has a stronger hand, the opponent will most likely bet and the player will call and lose all their money regardless. However if the opponent has a weaker hand, betting may be the only way to get the opponent's money into the pot, as checking allows the opponent the opportunity to check in turn.
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Freeroll Definition
Negative freeroll is relatively common in low stakes amateur play, but in higher stakes play allowing a negative freeroll on the final round of betting is a serious blunder.
Hypothetical example
In a game of no-limit Texas hold'em, in heads up play on the river with an $8000 pot, both players have $2000 remaining behind. The board is 5♠ 6♠ 9♣ 9♠ Q♣. If the player acting first holds 6♦ 9♦ they must bet to avoid negative freeroll even though they are losing to an opponent holding 7♠ 8♠, a pair of Queens, or the 9♥ with a Queen. In this case the higher holdings will almost certainly bet and the player will be compelled to call due to pot odds and hand strength, while lesser holdings such as a lesser full house, a flush, or a straight that would have called the bet may simply check to see the hand down. Furthermore, with only $2000 remaining to bet in a $8000 pot, checking to induce a bluff is unlikely to succeed against competent opponents.
Further reading
Harrington, Dan; Robertie, Bill (2006). Harrington on Hold'em: Expert Strategy for No-Limit Tournaments; Volume III: The Workbook. Two Plus Two Publishing, pp. 41-56. ISBN 1-880685-36-1.
Freeroll is a type of poker tournaments (multi table tournaments) with free entrance (no buy-in or buy-in in points) and guaranteed prize pool in real money, tournament tickets or material values. Freeroll is a free poker tournament.
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Freeroll Definition
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