If you win a lawsuit and have to reimburse the insurance company for medical expenses can you deduct those medical expenses?

You should be able to claim the medical expenses against your income tax, but there are limitations. You may have to claim them for the year that they were incurred. Which may mean you have to re-file taxes for that year. And Medical deductions are subject to a percentage offset. Consult your attorney, who should tell you when you get your award, or consult a tax expert. I gather what happened is you had medical expenses that were originally paid by (say your) insurance company. And instead of subrogation, you continued the lawsuit and won. The money you won had to be returned to the insurance company that already paid you for it (recovered). It is all going to offset - you can't deduct the medical expense unless you claim the income from the insurance company paying you for the lawsuit. But, the easiest handling would be just like any other covered medical expense...your insurance deductible and such costs are income tax expenses if they are above the minimums (unlikely).