Would you take this deal?

[BobC]

I'm not a tax expert and I don't play one on TV, but do you have a monster box of Gregg Jefferies rookies, or some other collectibles you could sell at a big loss, to offset this transaction? Would that work?


Sorry Mark, nice try though. LOL

If you are a collector, selling your collectibles, you cannot deduct any losses from the sale of one against the gains from another.

Now, and I've said this on the forum before as well, if you can prove to the IRS somehow that you were not a collector, and that you actually bought your card(s) strictly as investments, then you can offset the losses against other gains, and potentially against other income as well. And if you could do that, convince the IRS you card(s) were not collectibles and were only investments, your federal long-term capital gains tax rate would be maxed at 20%, not the 28% it is for collectibles.

The problem is that the IRS has historically viewed and defined sports cards pretty much all as just collectibles. It is only most recently that sports cards are starting to look more like a possible type of investment after all. Trick is how to then convince the IRS to agree with that assessment for cards you bought strictly as investments. It will probably take someone willing to go to court with the IRS, and winning their case, for that to happen. And unless we are talking about a T206 Wagner, or some other cards in the six to seven figures, and up, range, I can't see anyone willing to spend the time and money to fight the IRS in court to prove that sports cards can also be investments as well for tax purposes. But I can see someone eventually trying to fight the IRS on this down the road.