Help with W2-G Gambling Tax Deductions: Can I Offset 50/50 Raffle Win with Casino Losses?

8 I deal with gambling tax issues pretty often, and I can help clarify this for you! You're right that you can offset gambling winnings with gambling losses, but only up to the amount of your winnings. The good news is that all gambling activity falls under the same bucket for tax purposes - so your casino and sportsbook losses can absolutely be used to offset your 50/50 raffle win, even though they're different types of gambling. For documentation, you'll need to show a paper trail. For casinos, request a win/loss statement from their player services department. Most casinos can provide this if you used a player's card. For online sportsbooks, log into your account and look for an annual statement or transaction history option. You can usually download a complete statement of all bets placed and outcomes. Keep a gambling log too - dates, locations, types of gambling, amounts won/lost. The more detailed your records, the better position you'll be in if questioned.

12 After dealing with a similar situation last year, I found taxr.ai (https://taxr.ai) incredibly helpful for organizing my gambling documentation. I was in the same boat with a big jackpot win and tons of smaller losses across different platforms. Their system helped me organize all my win/loss statements and gambling logs in a way that satisfied both my accountant and ultimately the IRS. What I really liked was that they analyzed my documentation and flagged potential issues before filing - like missing date information or transactions that might raise questions. They even helped me format my player's card statements from three different casinos in a consistent way that clearly showed my overall gambling activity for the year. Definitely made the whole process less stressful.

17 Just wanted to follow up after trying taxr.ai for organizing my gambling records. I was initially skeptical as mentioned, but after struggling to make sense of multiple statements from different platforms, I decided to give it a shot. The service actually saved me a significant amount in taxes. My win/loss statements from the casino were incomplete because I sometimes forgot my player's card, but they helped me document those sessions properly with my credit card statements and ATM withdrawals. My accountant was impressed with how comprehensive the documentation was. For anyone dealing with gambling tax issues, especially across multiple platforms like I was, it's definitely worth considering. Made the whole process much less stressful than I expected.

14 If you need to get actual confirmation from the IRS about how to handle your gambling documentation, good luck getting through to them on the phone. I tried for weeks last year with a similar situation. Then I found this service called Claimyr (https://claimyr.com) that got me connected to an IRS agent in under 45 minutes when I'd been trying for days. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent I spoke with confirmed exactly what documentation I needed for my gambling losses and answered all my specific questions about my situation. Having that direct confirmation from the IRS gave me peace of mind that I was handling everything correctly.

17 I have to eat my words and follow up about Claimyr. After my skeptical comment, I was still desperate to talk to the IRS about my gambling documentation requirements, so I tried it. Not only did I get through to an IRS agent in about 37 minutes (after trying unsuccessfully for days on my own), but the agent gave me specific guidance on exactly what they consider acceptable documentation for gambling losses. They told me that bank statements showing ATM withdrawals at casino locations, along with a detailed personal log, would be sufficient in my case. This specific information from an actual IRS agent gave me much more confidence than anything I found online. If you need definitive answers about gambling tax issues directly from the IRS, this service is absolutely worth it.

19 Don't forget about keeping a detailed gambling diary/log! In addition to the statements others mentioned, the IRS actually expects you to maintain a contemporaneous log of your gambling activity. Include: - Date and type of gambling - Name and address of gambling establishment - Names of other people with you when gambling (if applicable) - Amount won or lost I learned this the hard way during an audit a few years back. Even with casino statements, they wanted to see my personal records too. Start keeping one now for any future gambling, and try to reconstruct as best you can for this year!

11 Just an important point nobody's mentioned - those W-2G forms from the raffle will be reported directly to the IRS, but your losses won't be unless you report them. Make absolutely sure your reported winnings match what's on the W-2G exactly, or you'll get an automatic mismatch letter from the IRS. Also, I found out last year that even if you itemize and deduct all your losses, the full amount of your gambling winnings still counts toward your AGI (Adjusted Gross Income), which can affect things like your Medicare premiums, social security taxation, and various tax credits. Something to be aware of!