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In that case, you'd report the medical expenses related to the incident as miscellaneous (other) income. Punitive damages are taxable except in certain wrongful death cases, as are awards for employment discrimination and injury to reputation (libel, slander, defamation, etc.).
Money and prizes won by gambling are considered income and subject to federal income tax. You have to report all of your gambling winnings on your tax return. You must include all cash winnings and the fair market value of non-cash winnings as taxable income.