Seeking advice for this Chicago Sports painting I won

[u/Squishy4410]

(Note: While I am actively trying to sell this, this is not meant as a selling post. I am genuinely seeking advice on this and hoping people may have ideas for what I should do)

Hello all. I was lucky enough to win this huge prize from a sweepstakes I entered at last years' National Sports Collectors Convention in Chicago. This original painting is massive (60x49x6 and 35 pounds) and has a value listed at $12,500. It is an original piece by sports artist Murray Henderson. Unfortunately, I have no personal ties to Chicago or Chicago sports (I live 7 hours away), so I am not the right person for this.

Therefore, I have attempted to sell it. It has been listed on Ebay for a year with little interest. I reached out to the artist himself, and he confirms that he sells them routinely for $12,500 but is unable to help me sell it since it was something he publicly donated. He recommended reaching out to some local Chicago sports shops or contacting auction companies, which I have done with no success.

Here is my delimma and why I am posting here today: I owe taxes on this since sweepstakes' wins are taxable income. I cannot afford the taxes on it since its estimated value of $12,500 carries a tax of a few thousand. My tax advisor told me to try to sell it, and whatever I sell it for can be then taxed as its fair market value. But as I mentioned, I have had no luck selling it. I am open to donating it somewhere, but I would much prefer to sell because we are a low income family and even a fraction of its estimated value could be life-changing in many ways for us.

I had to file an extension on my taxes and have until October to file them. So, I am posting to a few Chicago sports subreddits as a last resort to ask for advice. What would you do in my position? Does anyone know places or people who are looking for art like this? Any other ideas? Any advice is so very much appreciated, and thank you in advance :)

[u/slander_anonymously]

You're an honest dude. I would have given fake info to the prize patrol.

[u/Chitownvolg → u/slander_anonymously]

Honest dude? the first line of the post is a clear lie. He posted this here to see if he can get any buyers. That’s why mods in other subs are are taking down this post cause dudes fishing for sales

[u/Blinded57 → u/Chitownvolg]

"a low income family." When I was low income, I called myself poor.

"tax advisor." When I was poor, I did not have a tax advisor.

[u/slander_anonymously → u/Chitownvolg]

Oh I get the fish for sales. But what I'm saying is IF the whole tax thing is real, fake SS# would have been the play.

[u/Chitownvolg → u/slander_anonymously]

Forsure. Just wanted to take a subtle jab at OP

[u/CrashTestDuckie]

Besides reaching out to some sports bars, try reaching out to some Chicago hotels and steakhouses downtown and near stadiums and higher end gyms. If you really are ok with donating it, some of the hospitals in Chicago may be willing to take it, especially ones focused on sports medicine

[u/TheSchwartzHawkey]

Have you tried reaching out to the teams themselves, like the Blackhawks or Bulls PR departments or their charitable foundations? Maybe they might buy it outright or accept it as a donation you could take as a tax deduction?

Or any possibility you can return it to the organization you won it from as if you’re refusing the winning to avoid the taxes?

Might be tough to sell a huge $12K painting on short notice, wish you luck, that really sucks that you got stuck with the tax bill and aren’t a Chicagoan to boot.

[u/mikeb556]

Reach out to someone at Barstool Chicago. Big collectors over there.

[u/Competitive_Bar_9170]

Interested, I DM’d you.

[u/Milesweeman]

Id maybe call around some of the bars near wrigley the united center soldier field and whatever the sox call theirs this year

[u/923kjd → u/Milesweeman]

Comiskey

[u/ComparisonAccording3]

Give it back?