Rashi on Sanhedrin 24b:19רש"י על סנהדרין כ״ד ב:י״ט
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24b:19כ״ד ב:י״ט

כל כי האי גוונא לאו אסמכתא היא - והיכי דמי אסמכתא כגון דאם אוביר ולא אעביד אשלם במיטבא (ב"מ דף עג:) וכגון משליש את שטרו דגט פשוט (ב"ב דף קסח.) דסומך על לא דבר דסבור כל זה בידי לעשות ומרישא כי מתני אדעתא דלא יהיב ליה לאסמכתא קא מתני דטועה וסבור לא יבא לידי כך אבל הכא לא סמיך אמידי דהא לא ידע אי נצח אי לא נצח ואפי' הכי אתני שמע מינה מספיקא אתני גמר ואקני ולא גזילה היא:

any agreement such as this is not considered an asmachta -- a true case of asmachta involves a situation in which the man obligating himself has reason to believe that he will not actually have to pay. For example, one who contracts to work his neighbor's field and stipulates that if he does not live up to his agreement he will pay a fine, never really expects to pay, because he feels confident that he can do as promised. Another example: Reuven, a debtor, pays 50 zuz of the 100 that he owes to his creditor, Shimon. To assure Shimon that he will repay the remaining 50 zuz in a timely fashion, Reuven gives the note of indebtedness to athird party, Levi, and states that if he, Reuven, does not pay the balance by such-and-such date, Levi should return the note to Shimon, thus enabling him to collect the entire 100 zuz. Reuven does not really expect to have to pay the additional penalty, because he believes that he will be able to meet his obligation on time. Since both these cases are asmachta agreements, if the contractor is unable to work the field or the debtor is prevented from paying on time, he is not subject to the agreed-upon penalty. A wager, though, does not constitute an asmachta, because each player realizes that as skilled as he may be at the game, the outcome is nonetheless governed by chance. Therefore, he is resigned to pay if he loses, and the winner is thus not guilty of stealing.