Another frustrating win

I won a trip to Costa Rica in 2019. They arranged and paid for everything in advance and I was never 1099'd. Never paid taxes on it.

The value of the trip in question would be added to your gross income before any deductions. It's not a flat tax on the $3,600. Your adjusted gross income (income after deductions) would have to be over $534,600 to be taxed at 37%, and if your AGI is that much, why fret over $1500?
 
Taxes should be considered unless there is a cash option a lot of these contests value the prize way higher than I would pay. I don't believe not getting a 1099 will excuse you if there is an audit although chances of audit are probably low
 
Thank you all for your feedback - I guess the main takeaway is to read the rules carefully and only sign up for Sweepstakes with prizes that are worth the tax amount (for me).
In 1995 I won a trip to the NCAA tournament where Virginia, Memphis, Kansas and Arkansas played and it costed $1,600.00 and that year I think I owed approximately $400.00 in taxes. It was a wonderful trip and Gillette gave me $300 to spend. I think my younger brother and we had a great time. I also was there along with 22 other contestants to win a chance at $25,000.00. Unfortunately, only one person hit the 3-point $25,000 shot. It still was a blessing to go. Gillette even catered a watch party in a presidential hotel suite with lots of food and drinks. I have won other trips over the past few years but nothing like that. Keep entering contestants but you will never know who you might meet at the event. I met coach Nolan Richardson because the Arkansas Razorbacks stayed in the same hotel as us. Good Luck! Remember, many people enter but few people win.
 
Hello all, I was just notified that I won a $3,600 travel package to Indianapolis Race Track, however since it has no cash element I will have to pay the taxes out of pocket, which would be around $1,500. Hence, I had to decline. Any ideas on how to deal with it?
Many ask for cash offer only, if they can't travel for some reason.
 
Hello all, I was just notified that I won a $3,600 travel package to Indianapolis Race Track, however since it has no cash element I will have to pay the taxes out of pocket, which would be around $1,500. Hence, I had to decline. Any ideas on how to deal with it?
All you need to do when you have a big win is to offset the win with losses, since entering contests is considered gambling. So all you need to do is collect that amount in State or any Lottery tickets, you can use the ones you have purchased, or by any other means such as gifts, etc.
When you do your taxes, you put in the "income"(1099 form) from the WIN, and then offset it with the total of the Lottery tickets - so you don't pay any tax on your win.
Also, when you win, you pay Fair Market Value on your win. A lot of prizes costs have been exaggerated to make it seem better than it is. For example - if you win a trip, and they say airfare is $1000 - then you find a cheaper one for say $500 - that comes off the total winnings, same for hotels and meals. (Fair Market value for a car is much lower than what you think you have to pay taxes on)
Always ask the contest sponsor for an itemized list of your win.
Hope this helps, sometimes you still have to pay taxes, like on a car or something big, but usually you can offset them with the lottery tickets. But even with a car, you can offset a lot of the taxes with lottery losses.
 
It will be added to your final tax bill based on your current income. I would just set $1,500 to the side.
You can offset any win with losses, since Contesting is considered Gambling, so you can add up all the losing Lottery Tickets you have and enter into your tax return under Gambling Losses. (must itemize taxes)
 
Hello all, I was just notified that I won a $3,600 travel package to Indianapolis Race Track, however since it has no cash element I will have to pay the taxes out of pocket, which would be around $1,500. Hence, I had to decline. Any ideas on how to deal with it?
I don't believe a tax rate of 41% is valid even in your state. When I won a substantial prize I increased my federal withholding by $10 per pay to make up any deficit. Double check with your state before giving up claiming a prize like that.
 
Are they making you pay upfront for a withholding or in your next return? Also, what race? If it's the 500, you can probably make that money back selling it.

What a buzzkill though. Worse than simply not winning it.
Thought about it, but they wouldn't give some items of the prize, it's all or nothing
 
I won a trip to Costa Rica in 2019. They arranged and paid for everything in advance and I was never 1099'd. Never paid taxes on it.

The value of the trip in question would be added to your gross income before any deductions. It's not a flat tax on the $3,600. Your adjusted gross income (income after deductions) would have to be over $534,600 to be taxed at 37%, and if your AGI is that much, why fret over $1500?
I wouldn't fret if that was my income :) in NY you need to add state and even local taxes, which can be almost 10%
 
You can offset any win with losses, since Contesting is considered Gambling, so you can add up all the losing Lottery Tickets you have and enter into your tax return under Gambling Losses. (must itemize taxes)
Very interesting idea! thanks!
 
I'll take it... might not get 1099... I rarely do

You could still have to pay taxes even if you don't get 1099'd.

The IRS auditing you is pretty rare, depending on your income and how you file your taxes.
 
Your outcome is why I tend to steer away from prizes that are trip/travel related. Some even offer no transportation and they seem to inflate the value of the prize. Trust me, you will get a 1099 for the full stated value. I dont even know if you can transfer it to someone else. Good luck.

I have never won a prize where I could transfer it to someone else. NEVER.
 
Back
Top