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Hi, I know this is late but still helpful information, and I’m actually building a course on profitable sports betting and demystifying gambling taxes for professionals and more casuals, it’s no surprise that these people you asked didn’t comprehend the question in its complete form because the IRS is so unclear on gambling taxes…

All gambling income is taxable and USUALLY can’t be netted unless a professional, this means that for sports betting for instance you are taxed on your gross winnings, typically if you receive a W2-g perhaps a misc for wins over $600 with a wager requirement of 300x some sportbooks like DK & Fanduel do have other thresholds as well which is why they are in more states than other books but this circumstance might have your win $ loss look like this… DK $100,000 in winnings 

FD -40,000 in winnings for a net of $60,000 unfortunately they don’t let casuals net unless itemizing which is not as popular with SALT CAP (this will change in 2025/2026 hopefully when Tax cut is removed and itemizing becomes more appealing) but you will be taxed on $100,000 to make it simple it could be much worse but I’m assuming you never had a winning bet on FD to make this simple. Paying far more taxes on income that isn’t real is a real issue and is avoidable by becoming a professional OR SESSION GAMBLING session gambling is very unknown as there is no court cases on it the IRS are only clear on session gambling for slotted, I don’t think it’s wise to consider a session more than 1 day unless it’s a tournament spanning over more than 1 day. I use a lot of arbitrage sports betting and if I wasn’t a professional I would try to session gamble each individual ‘trade’

for instance Travis Kelce Over .5 TD +155 $3,000 (DK)

Travis Kelce Under .5 -125 $4,250 FD

This is an arbitrage bet, no matter what side wins the dollar amount won is $400 but IRS doesn’t wanna tax only $400 they want a bigger piece to tax which is ridiculous so for casuals that have these situations come up a possible solution is Session Gambling even though these are two different sportbooks I believe it is possible to session these because it’s the same event/bet placed at the same time and then this would be a session ending in $400 in proof it/income it’s important to note negative winnings (losses in a gambling session can’t be subtracted from a previous gambling session winning that losing session basically evaporates into thin air. 

gambling session is 100% a thing and you can’t ask anyone at H&R Block about gambling taxes because they are scared of their own shadow in regards to gambling taxes, I would seek out a CPA probably in the Vegas area as they will have far more experience. For me it’s a business, and the IRS is tricky with what constitutes someone being a professional as well, there are court cases on that matter if you are curious, basically stating treating it in a business manor (daily log, expenses, time, location (state & site) wins & losses type of bet, if it was money or bonus funds etc, having records to back that up goes a long way to being a professional this whole 40 hours a week and not having other income is just spooky no other buisness has those requirements to being a professional, and their is a trucker case where they have other income and are still professional odds are you won’t have to deal with this in court being a professional unless you don’t make profit, don’t record keep, switch between benign a pro and not, so don’t abuse this. I think being. Aggressive with gambling sessions the way I explained is possible it’s likely you will be asked about it by the IRS but highly doubt they want to go to court over something like what I showed it’s the same bet in the same player just on a different side on different sports, because the IRS is not clear (left vague on purpose) my belief is this is totally doable until they close this loophole for casual gamblers. Not a Licensed CPA or anything but this is my two sense and would recommend contacting a professional that’s not scared of their own shadow. Best of luck!