He received a 1099 Misc. 0ther income for $ 5500.00 he kept a journal re losses from the race track for $ 20,000.00 which were cash draw from his bank account can he write off the $ 5500.00 on schedule A as an expense against this, like when you receive W 2 G.
Either the racetrack used the wrong form, or the $5500 was for some kind of services. I’d try to get a corrected form using the 1099G. Otherwise, treat it as a gambling winning and take the losses on Schedule A