About

What you need to know to maximize your free winnings

Purpose

This website is designed to help users analyze, compare, and structure sports betting opportunities from a mathematical and risk-management perspective. In other words, to help you. In no way do I support the rampant gambling industry that preys on addicts. New user promotions are in essence a door these corporation use to give people a taste of the thrill of gambling. They make money not from the recreational sporadic gambler but from the addicts that lose tremendous amounts and gamble not from reason but because of a medical disease. It is for this reason that I cannot urge enough that you should never start on the path of making a single wager that is not fully arbitraged for a profit independent of any outcome. While you may be an individual that would not fall into this trap, remember that a potential gambling addict thinks that very thing and that intelligence by no means protects a person. So, after fully utilizing new user promotions, it is surely in your best interest to self exlcude yourself from a sportsbook.

Taxes

By the letter of the law, all gamblings winnings are taxable and should be reported even if no tax forms are issued. Any losses can only be deducted from winnings if you itemize your deductions, and even then you can only deduct up to 90% of your winnings on your federal taxes. Therefore, if one was going to report every single wager they made, even if no tax forms have been issued and there is no way the IRS would have known about your gambling, it does not make financial sense to place any wagers.

With that said, let me clear up what actually goes on. While I can't openly promote tax evasion, you should know:
  • The current threshold for 2026 tax year for issuing 1099-MISC is $2000 as a result of Trump's One Big Beautiful Bill Act which raised it from $600. Moving on to the 2027 tax year and so on, the $2000 figure will continue to rise in accordance with inflation. Betting platforms that issue 1099-MISCs may still on reference in customer support and on their websitess this old $600 threshold but trust that by February 2027 these platforms will 100% be using the $2000 threshold.
  • Online sports gambling — whether through state-regulated sportsbooks/DFS or sweepstakes/social sportsbook platforms — operates within regulated financial systems that require full KYC (Know Your Customer) identity verification, typically including your legal name, date of birth, address, and often your Social Security number before withdrawals. As a result, there is a clear digital paper trail linking you to the platform and your transactions. However, unless a reportable tax form (such as a W-2G or 1099-MISC) is generated and transmitted to the IRS, the federal/state government will not be aware that you engaged in any gambling activity. Similarly, standard ACH deposits to and withdrawals from state regulated or sweepstakes platforms are processed like ordinary bank transfers and do not trigger IRS notifications (i.e. a tax form) simply because the transaction involves a gambling operator -- frequency or sizes of these bank transfers do not change this fact.
  • Traditional sportsbooks (i.e. DraftKings, BetMGM, Fanatics, etc.) will not report net winnings. Instead, they will only issue a Form W-2G for indivudal wagers that net at least $2000 and payout at least 300 times the wager amount. An enormous longshot wager like the type that would trigger a tax form would never be placed by a gambler simply using arbitrage for guaranteed profits.
  • If you are taking advantage of a new user customer promotion on a Pick'em platform (i.e. PrizePicks, Underdog, Chalkboard, etc.) a 1099-MISC tax form will be issued if you have net earnings in a calendar year of at least $2000. Simply arbitraging wagers that exploit new user promotions and the free picks new customers receive, will not lead to netting $2000 (without promotions, there is for all intents and purposes no reason to use these apps which give heavily reduced payouts).
  • Platform-funded sweepstakes/social sportsbooks (i.e. Fliff, Onyx, Thrillzz, ReBet, etc) where you purchase virutal coins that can be wagered and then redeemed for cash, are supposed to issue a 1099-MISC if you redeem (not net) at least $2000 in a calendar year. Utilizing a new user promo on these platforms which generally aren't that rich anyway, will 100% not get you near that threshold (Betr the exception), and because these apps typically don't have the tightest lines, you wouldn't even want to make large hedge wagers on them. I know I said redeem here, but it seems having talked to customer support at ReBet at least, they are saying they determine the threshold based on your net winnings of their virtual cash currency - and even then I know people who passed this threshold and still didn't receive anything. Whatever the truth is, it's better to be safe and not redeem more than $2000 from any one of these platforms, which I emphasize shouldn't happen even if you were not concerned about this threshold -- the one exception is Betr Social Sportsbook because they offer new users a 25% first purchase bonus match that is not capped. In this instance, simply purchase the $999.99 package rather than the $9,999 one.
  • Platforms like Kalshi are regulated financial exchanges under the Commodity Futures Trading Commission which means they, like a broker, will issue a 1099-B for all trades - friend referral bonuses are separate and given the $2000 threshold, will not lead to any tax forms.
  • Sporttrade is a licenced and state regulated sports betting exchange which means instead of a 1099-B, they like traditional sportsbooks, have a near impossible threshold for issuing tax documents -- the new user promtional cash back up to $100 may go toward a 1099-MISC threshold but this would certainly not amount to the IRS threshold.
  • Peer-to-peer sweepstake model social sportsbooks like NoVig, or 4Cx purposefully operate in a gray area that allows them for your purposes to not have to issue tax documents. By being peer-to-peer, redeeming virtual currency is argued to not be a payout from the platform but from other betters, a specific legal distinction that negates a 1099 requirement. Since this whole industry is still the wild west, the future of P2P in the coming years could change, whether that means more state issued cease and desist orders or legal model shifts. However, any regulatory reinterpretation if it even were to occur in the coming years, would unquestionably be prospective only.

In summary, taxes on gambling winnings, in no small part to the gaming industry and their lobbyists, rely almost exclusively on self reporting and are thus heavily underreported. The industry itself is rapidly changing and regulators are still trying to catch up on emergining businesses that exploit legal loopholes. However, this effort is focused almost exclusively on ensuring consumer protections and collecting large tax revenues from the platforms themselves. After all, the incredibly narrow W-2G thresholds are a policy choice, not an oversight.