No. Gambling winnings must be reported as income, but gambling losses are deductible only as an itemized deduction. There is no dollar limit on the write off but it’s limited to the extent of the gambling winnings.
For 2007, a high deductible health plan is a health plan with an annual deductible that is not less than $1,100 for self-only coverage or $2,200 for family coverage, and with annual out-of-pocket expenses that do not exceed $5,600 or $11,200, respectively.