Preparing for my tax return this year, I face a small conundrum. A longtime successful offshore gambler, I have registered token profits over the years ($50-300); in some years I’ve lost similar amounts. I always maintain a record of my wins & losses but, due to those small final outcomes, have never declared any profit. 2019 was a particularly good year and I am planning to enter a profit on Schedule 1 (Other Income, Line 21).
My profit amount is small (less than $3000), but what I’m really doing is buying Peace Of Mind. In short, I don’t want The Man knocking on my door for an audit three years from now and finding myself flat-footed for a documented explanation. I know the chances of such a reckoning are slim (retrieved cashed bank-checks), but I’d rather pay the 2019 tax than endure the psychological trauma.
Naïve and overly cautious? Likely. But I’d rather emulate some good friends, one of whom worked for the IRS. When filing their annual taxes, they went out on NO LIMBS whatsoever – a lifetime of returns -- pure as the driven snow.
Please share your thoughts and the very best (innocuous) descriptive phrase that should be placed on my Line 21.
Thanks,
TheKingfish
Sun Mar 08, 2020 3:04 pm
InstantAdamD New Member
Cash: $ 1.20
Posts: 6
Joined: 25 Apr 2015
For such small amounts why would you ever do that?
