What to do after a sizable win?

[Dunbar]

Originally Posted by casp0555

I don't think you have to pay taxes on any winnings unless they are 300 times the total wager, I may be wrong but that's what I believe the new tax rules are since 2017????

That may be the rule for receiving a Form W-2G, but the IRS still wants you to pay tax on any gambling winnings. As I understand it, the sum of all your winning days at the track are taxable. And you can only deduct the losses of your losing days, or losses from other kinds of gambling, if you itemize. (or if you file a Sch C as a professional gambler).