gambling

man in forground, big TV football game in background

I won $8,500 gambling on sports this year. My uncle told me that if it’s under $10,000 I don't have to declare it on my taxes. Is that true?

You had a good year betting on sports, and when it was all said and done, you were ahead by $8,500. Then your uncle gives you even more good news: you don't need to worry about taxes because it's under $10,000. Sounds great...if it's true.
June 29, 2026 Jesse Singer
sad man at casino table

I lost big at the casino last week. If the IRS taxes gambling winnings, can I write off all my losses?

You walk into a casino hoping for a lucky night. But while you might know that the IRS wants its share when you win, the bigger question for most of us is: can we write it all off when we lose? The answer is more complicated than most gamblers realize.
June 18, 2026 Jesse Singer
Internal - Same Game Parlays

My brother spends $50 on game parlays every Sunday. Should I tell him that I think he has a gambling problem over $50?

My brother spends $50 on game parlays every Sunday—should I worry? Here is how to tell whether a small weekly betting habit is harmless fun or a sign of a bigger gambling problem, plus how to bring it up without starting a fight.
April 21, 2026 Jack Hawkins
Sportsbettinginternal

Sports betting is now a multibillion-dollar growth industry, but 95% of people who bet lose money over the long term.

Sports betting was effectively legalized in 2018 and the industry has grown faster than anyone anticipated.
December 4, 2025 Quinn Mercer
Brotherbettinginternal

My brother’s constantly broke but spends hundreds on sports bets. He wants to move in with me rent-free but only “for a little while.” What now?

Few situations test your patience like a sibling who’s broke, irresponsible with money, and now asking to move in with you. We look at how you can help without compromising your finances.
November 11, 2025 Quinn Mercer
Husbandgamblinginternal

My husband hid over $100K in gambling debts while I thought he had the money invested. At 55, our retirement is off-track. What happens next?

It can be devastating to discover hidden debt if you're in your 50s, but there are steps you can take to protect your future and your retirement.
October 29, 2025 Sammy Tran