can you deduct gambling losses if you don t itemize. One of them is you cannot claim losses greater than winnings. can you deduct gambling losses if you don t itemize

 
 One of them is you cannot claim losses greater than winningscan you deduct gambling losses if you don t itemize Sports betting losses might also be used as deductions if you itemize your deductions and keep a detailed record of wins and losses

It’s also important to note that the only way you can deduct gambling losses is if you are already itemizing your deductions on a Schedule A. Colorado state income tax and gambling winnings. Yes - gambling losses are deducted as a part of itemised deduction - on schedule A. Taxpayers who take the standard deduction are generally unable to deduct their sports. Michigan gaming but also would allow them to deduct losses attributable to gaming that did not occur in Michigan. You. However, you can claim your gambling losses as a tax deduction if you itemize your deductions. Additionally, winnings and losses must be reported separately, i. A W-2G form isn’t necessary in cases where: You have won no more than $1200 on slots; You have won up to $5,000 from poker;. So if you lose $500 but win $50, you can only deduct $50 in losses on your federal income tax returns. The IRS will be on you immediately if you don’t. You have to actually have to have winnings to be able to deduct losses. Also note that to report gambling losses, you must choose to itemize your deductions instead of taking the standard deduction. You can only deduct gambling losses up to the amount of your winnings if. This limitation applies to the combined results from any and all types of. TurboTax prompts you to enter your gambling losses after you enter your gambling winnings. In deluxe version when I claim the loss amount As the same amount as the win it does not change my refund amount back to where it was before. For tax purposes, gambling losses are tax deductible if you itemize your deductions and can provide detailed records of your winnings and losses. They can decrease your taxable income. That is, if you won $50,000 and lost $55,000, you could only deduct $50,000 of your losses. Gambling Losses are reported on Form 1040 Schedule A as a Miscellaneous itemized deduction. Example: John wins $23,500 during the year playing slots and other casino games. So if you make $60,000, and you choose the standard deduction amount of $12,550, your. 205 - Capital Gains and Losses: 03/06/2023: 206 - Pensions and Annuities: 03/06/2023: 207 - Farming and Fishing Income: 03/06/2023: 208 - Gambling Income and Expenses: 03/06/2023: 209 - Nontaxable Income: 03/06/2023: 210 - Earnings of Clergy: 03/06/2023If you itemize deductions, you can deduct your gambling losses for the year on line 27, Schedule A (Form 1040). Furthermore, you cannot offset your. You can’t deduct your losses without reporting your wins. For example, let’s say you have $2,000 in recorded wins at Golden Nugget Casino Michigan but $3,000 in recorded losses. Or at all for that matter. If you claim the standard deduction, y ou don’t get the opportunity to reduce taxes for winnings owed by deducting gambling losses. Generally, if your deductions exceed $2,690, it will benefit you to itemize. You will then pay taxes on the $500 net profit if you can itemize. You can't deduct it directly from the winnings. If somebody with $300k losses has been reporting. It is the last category listed. ) The sessions will always break even (unlikely) or net out as a gain because losses are not allowed between sessions. If you do not itemize , there is nothing you can doYou cannot adjust the w-2 by the losses. Gambling Losses. If you’re in the red for the year, don’t expect to recoup those losses with tax deductions. For a married couple filing jointly, the wagering winnings of. 1040 Page 2: Income Tax. You can’t deduct gambling losses if you take the standard deduction. This form is used to report the winnings as taxable income. In the U. If you do elect to itemize your federal deductions, calculate all your gambling losses from the year. But even if you don't receive forms, the IRS mandates you report gambling wins as income. But the IRS wants to see that W-2G, so. However, if you have $5,000 of winnings and $10,000 of losses, you can only deduct $5,000 of losses. citizen or resident alien for the entire tax year. Itemized Tax Deductions. Individuals who don’t use excess itemized deductions are more likely to see a tax cut. So you can use losses to “wipe out” gambling income but you can’t show a gambling tax loss. If you are a Wisconsin resident and paid a net income tax to another state or the District of Columbia on gambling winnings, you may be entitled to claim a credit for net income tax paid to the other state on your Wisconsin. For example, if you had $10,000 in gambling winnings in 202 2 and $5,000 in gambling losses, you would be able to deduct the $5,000 of losses if you. Some states either don't allow a deduction for gambling. You cannot claim gambling losses if taking the standard deduction. John reports his $23,500 of wins on Schedule 1 and $23,500 as an itemized deduction on Schedule A. Note that if you don't itemize, you can't deduct your gambling losses: If you had $5000 in winning sessions and $6000 in losing sessions, you have to report the $5000 as income, and you can't subtract out your losses, because you're not itemizing. You can claim your gambling losses as “Other Itemized Deductions” on your income tax. LISA GREENE-LEWIS: Right. So you can use losses to “wipe out” gambling income but you can’t show a gambling tax. Itemized Deductions: To deduct gambling losses, you will need to itemize your deductions on Schedule A of your federal tax return. For 2022 tax returns (those filed in 2023. If you had a big win, are concerned about your tax liability, or have any questions related to gambling winnings or losses, contact the. In addition, gambling losses are only deductible up to the amount of gambling winnings. Some states have poorly written laws. Another deduction you can take on your federal return to try to nip away at your tax bill is for the income taxes you must pay to your state on your winnings. Here are five bad days — and ways that tax experts say you could turn them into a smaller tax bill. Starting in 2021 if you elected to itemize deductions on your federal return (you did not take the standard deduction) and deducted wagering losses from casual gambling, you may be eligible to deduct wagering losses. Level 15. They’re deductible, but only as itemized deductions. If you itemize your tax deductions you may be able to deduct some of your gambling losses. If you don't have enough other deductions to itemize, then it is to your. Changes Under the Tax Cuts and Jobs Act There is a threshold requirement for the gambling losses deduction, which means that you can only deduct losses that exceed 2% of your adjusted gross income (AGI). If you only claim standard deductions, you can’t use poker losses to offset your payable taxes. Gambling losses can only be deducted up to the amount of the gambling winnings. The Tax Court's decision. If you do not have enough itemized deductions to exceed your standard deduction, the gambling losses have no effect at all. Finally, gambling losses can, in certain circumstances, trigger the dreaded Alternative Minimum Tax (AMT). In general, individuals not in a trade or business or an activity for profit, may take a standard deduction or itemize their deductions. You may only deduct gambling losses, to the extent of gambling winnings. Amount of your gambling winnings and losses. Charitable Cash Contributions, Even If You Don’t Itemize. The deduction however, unlike the gambling deduction, is subject to the 2%. You can also deduct certain casualty and theft losses. "You can deduct those losses to the extent of your winnings," Allen said. You may or may not receive Form W-2G Certain Gambling Winnings, but you can report all gambling winnings in the same place in the TaxAct program. Need a coach for filing your income taxes?DoninGA. Then there is MS, that charges a 3% nonrefundable tax to all nonresidents. Contributing to a 529 college savings account can offer tax advantages, including tax-deferred growth and tax-free withdrawals for qualified education expenses. Any information provided to you on a Form W-2G. And in order to deduct your losses, you have to be able to itemize your deductions. You may deduct gambling losses only if you itemize your deductions on Schedule A (Form 1040) and kept a record of your winnings and losses. For taxpayers who do not gamble as their trade or business, losses from gambling transactions can be deducted as an itemized deduction to the extent of any gambling winnings. You must report your gambling winnings even if Wisconsin income taxes are not withheld. Winnings are reported as "other income" on Schedule 1. You may deduct gambling losses only if you itemize your deductions on Form 1040, Schedule A ) and kept a record of your winnings and losses. To make. The IRS takes a broad view of what constitutes a. The winnings will still show up as income. You can deduct gambling losses on your tax return, but only if you itemize your deductions. If you used your players card, you. For additional information on withholding gambling winnings, please contact the office. The additional losses are not deductible. Your total gambling deduction is limited to $800, the amount of your winnings. "But, you must itemize your deductions. Can i deduct gambling losses { $5,000 } even if i don''t itemize? Ask an Expert. Therefore, if you lost $3,000 gambling, and won $1,000 of it back, only $1,000 can be deducted as a. So, you should keep: An accurate diary of your gambling winnings and losses1. My point is if you only have evidence of a $50k loss that is all I would claim. If you itemize, you can deduct $400 for your losses, but your winnings and losses must be handled separately on your tax return. For New York purposes (Form IT-196, lines 21 through 24), you can claim these deductions: 2017 IRS Publication 463, Travel, Entertainment, Gift, and Car Expenses So there you have it, that's what "itemizing your deductions" means. You should only itemize if all your personal deductions, including gambling losses, exceed your standard deduction for the year. With a refinance, you can deduct points over the life of the loan — so, as an example, you could deduct 1/30th of the points every year for a 30-year mortgage, which would total $33 per year for. YOU DO NOT PUT $500 IN THE INCOME SECTION. Maintaining a journal or similar. You report gambling winnings as Other Income on the 1040. While you can write off some gambling losses if you itemize, that deduction can’t exceed the amount of your winnings. You must include the U. ) A tax credit, on the other hand, is a dollar. You cannot use gambling losses to create or increase a tax loss. For New York purposes (Form IT-196, line 20), you can claim casualty and theft losses. For example, if you have $5,000 in winnings but $8,000. The Tax Court held that Coleman had substantiated that his gambling losses for 2014 were in excess of his gambling winnings, so he was entitled to the $350,241 gambling loss deduction. You may deduct $10,000. Meaning if you win $2000 and lose $5000, only $2000 worth of gambling losses will qualify for deduction, and the rest can still be taxed. If you claim the standard deduction, you won’t be able to write off. You can claim your losses as “other itemized deductions: gambling losses” on Form 1040, Schedule. You may take a deduction for the Indiana portion of the federal net operating loss deduction (NOL) you added back on line 2 of Schedule 1 (This will be a net operating loss deduction from an earlier year(s) carried forward to 2017. For your 2022 taxes, which you will file by April 18, 2023, teachers, counselors and principals who aren’t reimbursed for buying supplies can deduct up to $250. Gambling Loss Limitation. For information on withholding on gambling winnings, refer to , Tax Withholding and Estimated Tax. Due to the passage of the Tax Cuts and Jobs Act of 2017, most individuals choose to use the standardized deduction rather than itemizing deductions on their tax returns. 5 percent of the amount of your fed - eral adjusted gross income on Form OR-40, line 7, or Form OR-40-N or OR-40-P, line 29F. If you qualify to itemize your deductions, you can use this form to deduct your gambling losses. Practically, IRS auditors may allow some reconstruction of these expenses if. Also, the amount of gambling losses you deduct cannot be more than the amount of gambling income you reported on your return. However, the deduction for those losses must be included with “itemized” deductions. Claim your gambling losses up to the amount of winnings, as "Other Itemized. tax code is very broad in how it defines what is taxable. This is $52k of taxable income. One final note: casual gamblers can deduct gambling losses as well, but not the same way as professionals. On the other hand, a professional gambler can deduct other expenses associated with their casino play (it's a JOB after all - ha!). First, you can only deduct losses up to the amount you won that year. You can deduct only the part of your medical and dental expenses that exceeds 7. Claim your gambling losses up to the. 0 1 4,431 Reply. If you itemize deductions , you may claim gambling losses up to your gambling winnings. “The U. 4. However, gambling losses can only be claimed if you itemize your deductions on Schedule A of your Form 1040. You can deduct your $50,000 of gambling losses as an itemized deduction. When you win, the gambling establishment may issue you a Form W-2G if the winnings meet certain thresholds. Gambling losses go on schedule A line 28 and are not subject to the 2% threshold. In 2013, North Carolina passed the Tax Simplification and Reduction Act (), which increased the standard deduction but eliminated many of the itemized deductions, including deducting for gambling losses. Gambling losses are reported on Schedule A (the form for itemizing). This limitation applies to the combined results from any and all types of. you would have to report all $10K of gambling winnings in your income, whether to itemize with the offsetting losses or take the standard deduction is up to your specific tax situation. You can't use it to offset your gambling gains in other years. Finally, you. Conversely, you may only deduct gambling losses if you itemize your deductions on Schedule A of Form 1040. The winnings will still show up as income. So you ask, why not declare myself a “professional” gambler. If you don’t itemize you are screwed! You cannot deduct losses on a standard deduction. You can't deduct more in gambling losses than you have in gambling winnings for the year. Conversely, if you reported $12,000 of. This. For federal purposes, you can no longer claim an itemized deduction for a casualty or theft loss unless it is the result of a federally declared disaster. The amount of losses you deduct can't be more than the amount of gambling income you reported on your return. Also, the amount of gambling losses you deduct cannot be more than the amount of gambling income you reported on your return. Do you have to itemize deductions to claim gambling losses? Yes, gambling losses are only deductible as an itemized deduction on Schedule A. To deduct gambling losses, you must itemize your deductions: Claim your gambling losses as a miscellaneous deduction not subject to. The income from gambling shows up on the first page of your tax return. That being said, if you do itemize and your gambling losses are on your Schedule A, be careful. No. $27,700 for married taxpayers filing jointly or qualifying widows/widowers. Casual gamblers also must keep records of their gambling. If you’re in the red for the year, don’t expect to recoup those losses with tax deductions. Generally speaking, though, gambling losses are tax deductible only to the extent of gambling winnings. (If you're working online,. It is very hard now to get to deduct losses. So if you had winnings of $2,000 and losses of $5,000, your deduction is. Gambling winnings are unique because you can also deduct your gambling losses and certain other expenses, but only in specific circumstances (see our article about this). When you win $500 for one bet, you must report the entire $500 as taxable income. If somebody with $300k losses has been reporting. If you don't have enough deductions to itemize, your screwed. If they’re married to another educator and they’re filing jointly, the limit rises to $500. If you do not have enough to itemize, however, you cannot deduct the gambling losses. For example, if you won $5,000 in a casino but lost $7,000, you can only deduct up to $5,000 of your losses. Though you may not be able to deduct all your losses. Topic No. You may deduct gambling losses only if you itemize deductions. "For federal you have to show in the income on the 1040, your schedule "A" is where you take your itemized deductions and that's where you right off your gambling losses," Robinson said. Top videosItemized deductions. Based on your tax bracket, sports bettors in Pennsylvania could owe up to 35% of winnings to the federal government in addition to the 3. So you ask, why not declare myself a “professional” gambler. But whether you’re wagering on. Your losses can't exceed your winnings, though. Itemized deductions are expenses that you can claim on your tax return. nakor28 • 3 yr. You can include in your gambling losses the actual cost of wagering plus other expenses related to your. For tax year 2020, the standard deduction is: Filing Status 1: $2,110. Assuming you file jointly with your wife, the federal tax would only be 24% if your joint taxable. Claim your gambling losses up to the amount of winnings, such as Other Itemized Deductions. You can deduct gambling losses if you itemize your deductions on your tax return, but you cannot deduct more than the gambling income you received. The 2017 tax law, known as the Tax Cuts and Jobs Act, also modified the definition of “gambling losses” under Section 165(d). So, if you win $1,000 and lose $1,500 in another league, your deduction is limited to just $1,000. $1,000,000, you don't have to worry about other itemized deductions. You show the income,. You have to report that. However, if you itemize deductions on your tax return and claim losses (up to the amount of your winnings), then you may be able to deduct your losses on Line 27, Schedule A (Form 1040). That $300 applies whether you're a single filer or you file a joint return. S. The amount of losses you deduct can't be more than the amount of gambling income you reported on your return. Losses on line 16 cannot be greater than wins on line 8. Claim your gambling losses up to the amount of winnings, as “Other Itemized. “If you win $10,000 and keep gambling for the purposes of tax deductions, you can win $10,000 and then lose $10,000, and then you take home nothing. If you don't provide your Social Security number, the withholding will be at 28% and start at lower payment amounts. How much do you need to itemize for 2021? That might sound like a lot of work, but it can pay off if your total itemized deductions are higher than the standard deduction. If you win more than $600, venues send both you and the IRS a tax form, according to TurboTax. For example, if you win $2,500 from gambling but lost $4,500, you can only deduct $2,500 of those losses. All income from gambling). Losses: You can deduct gambling losses that don't exceed your winnings as itemized deductions using Schedule A (Form 1040), but you need to provide. However, if you do itemize, you can deduct the $1,300 as a gambling loss which will offset $1,300 of your gambling winnings. Gambling winnings are fully taxable according to IRS regulations but gambling losses can be deductible up to the amount of your winnings if you choose to itemize deductions on your tax return. 63%. You may deduct gambling losses only if you itemize your deductions on Schedule A (Form 1040)and kept a record of your winnings and losses. Once entered, you will be asked about gambling losses. If. They will tax you, at the state level, on gross winnings. The deduction can only be claimed if you choose to file. The policy allows you to deduct your gambling losses up to the amount you won during the year. It is very hard now to get to deduct losses. The deduction is equal to the wagering losses claimed by the taxpayer as an itemized deduction on the federal income tax return for the same tax year. • The amount of gambling losses you can deduct can never exceed the winnings you report as income. If you're in the red for the year, don't expect to recoup those losses with tax deductions. Another. Gambling Losses are reported on Form 1040 Schedule A as a Miscellaneous itemized deduction. Yes, you can deduct your losses if you itemize your deductions instead of taking the standard deduction. ‎April 4, 2021 2:00 PM. Losses can be claimed up to the amount of your winnings. Moreover, the Tax Cuts and Jobs Act (“TCJA”) modifies the limits on gambling losses for professional gamblers. However, if your total itemized deductions are greater than the standard deduction available for your filing status, itemizing can lower your tax bill. You can enter your winnings, and then keep clicking through the interview to enter gambling losses. “Taxpayers can deduct gambling losses only up to the amount of their gambling. And gambling losses aren’t deductible in the AMT. Canceled checks or credit card statements aren't enough—you need to keep receipts and other bills showing what you spent the money on. Ones total tax is based on a wide variety of factors. 02-01-2021 02:39 PM. For tax years prior to 2018 and after 2025, you can only deduct casualty losses not reimbursed or reimbursable by insurance or. $19,400 for head of household. You can only itemize your losses up to $10,000 on your tax returns. . Educator Expenses. You can claim your gambling losses as "Other Itemized Deductions. Itemized deductions are expenses that you can claim on your tax return. In other words, you can’t have a net gambling loss on your tax return. Winnings are reportable always. To deduct your losses from gambling, you will need to: Claim your gambling losses on Form 1040, Schedule A as Other Miscellaneous Deduction (line 28) that is not subject to the 2% limit. Gambling losses. Nov. However, your gambling loss deduction shouldn’t exceed your winnings. Example: John wins $23,500 during the year playing slots and other casino games. If you reported your $5,661 of income as 'hobby income', you would still need to itemize to deduct the $1,300 to offset any income. 1 Solution. The IRS allows you to claim your gambling losses as a deduction, as long as you don’t claim more than you won. Regarding your federal tax returns, you may deduct gambling losses only if you itemize your deductions on Schedule A (Form. In short: The only reason to actually deduct gambling losses would be if they — along with other deductions — are more than the standard deduction. When filing your return, you reduce your taxable income by subtracting the greater of either the standard deduction or your total itemized deductions — which may include charitable donations. However, these deductions may not exceed. As you pointed out, if there was no "session" gain, there there is $0 of taxable gambling income to report. You may itemize your deductions for Kentucky even if you do not itemize for federal purposes. The amount of losses you deduct can't be more than the amount of gambling income you reported on your return. Level 15. Gambling losses are not a one-for-one reduction. You actually have to have winnings to deduct losses, and then you can only deduct what you won. The bad part is say you win 10k and have. The gambling losses will be on Schedule A, if you itemize your deductions, as opposed to. As an example, let’s say that in a given year you went gambling twice, winning $6,000 in one instance, but losing $8,000 in. So, the. Form 1040 Schedule 1 and U. If they have $100,000 in W-2Gs, they can write off $100,000 in losses AND subscriptions to gambling resources, travel and meal expenses, home office expenses, and legal/professional fees. Additionally, you must meet a. 1. So that's one thing to. Meanwhile,. Ones total tax is based on a wide variety of factors. You can deduct your losses, but only if you itemize your deductions on Schedule A (Form 1040). Miscellaneous itemized deductions are those deductions that would have been subject to the 2%-of-adjusted-gross-income (AGI) limitation. The tool is designed for taxpayers who were U. For tax purposes, you can only deduct losses up to the amount of your winnings. If you itemize deductions, you can deduct your gambling losses for the year on line 27, Schedule A (Form 1040). If you were issued a W2G form for your FanDuel gambling winnings, it is mandatory to report them on your tax return. SHE OWES AT LEAST 25%. Casual gamblers also must keep records of their gambling. Online gambling and. In addition, you won’t be able to write off gambling losses unless you itemize your deductions. Gambling Losses and Itemized Deductions I have about $20,000 in gambling winnings with the same in losses. Gambling losses are an itemized deduction. Gambling losses can be deducted from. Statements. If you're in the red for the year, don't expect to recoup those losses with tax deductions. But the amount of losses you deduct can’t be more than your reported gambling income. Still, if your standard deduction is greater than your itemized deduction, there is no benefit to claiming the gambling losses. The cost of your food, lodging, etc. You can deduct gambling losses only up to the extent of gambling winnings, and the losses can't exceed the winnings. Gambling losses cannot be greater than gambling wins for the tax year. The amount of losses you deduct can't be more than the amount of gambling income you reported on your return. As we all wondered, unless you have enough deductions to actually itemize, you’re stuck paying taxes on all of the winnings and your losses get lumped into the standard deduction. Detailed records could be a diary of receipts, tickets or other records that show accurate amounts of bets. There is one golden rule to keep in mind when deducting gambling losses on your tax return. You can deduct gambling losses from your income, but there are a few catches. Form 1040 Schedule A. Gambling losses are deductible on your 2020 federal income tax return but only up to the extent of your gambling winnings. tax code is very broad in how it defines what is taxable. 5% of your income to be greater than the standard deduction. This means that out-of-pocket expenses for transportation, meals, lodging, etc. In other words, you can’t claim more in losses than you have in winnings, and you cannot claim the standard deduction. they can provide a win/loss report. However, for a casualty loss that is the result of certain federally declared disasters (Form IT-196, line. When wagering, there is the chance of incurring losses. Do online casinos report your winnings to. Gambling losses can be the hardest to prove IF you’re audited. Married taxpayers filing a joint return: $25,100. Updated: Mar 5, 2023 / 12:00 PM MST. Gambling losses are. Furthermore, you cannot offset your winnings from one day. You can claim gambling losses as a miscellaneous itemized deduction, but only up to the amount of your gambling winnings. Accurate record-keeping and supporting documents are essential to prove your losses, and you can only deduct losses up to the amount of. Since you lost $30k, you can itemize your deductions, file Schedule A, and prove to the IRS with a ledger and receipts that you lost $30k. For New York purposes (Form IT-196, line 20), you can claim casualty and theft losses. If you suffered gambling losses in 2022, you can deduct up to the amount of gambling income that you reported. Losses: You can deduct gambling losses that don't exceed your winnings as itemized deductions using Schedule A (Form 1040), but you need to provide records. You can’t deduct more than you won, even if you did actually lose more than you won during the course of the year. The full amount of your gambling winnings for the year must be reported on line 21, Form 1040. If you itemize instead of taking the Standard Deduction, you can deduct gambling losses up to the amount of your winnings. If you don't have enough deductions to itemize, your screwed. Enter your winnings in the Form W-2G topic or as Other Income. You would then enter total winning on schedule C and losses as business expenses. For example, if you spent $1000 at the casino but only won $200, you'll only be able to claim a gambling loss of $200. See more• The amount of gambling losses you can deduct can never exceed the winnings you report as income. 4. With $10,000 in winnings, you can deduct combined losses up to that amount. Residents: report the amount of wagering losses you. Professional gamblers don’t have to itemize to claim losses—those also can go into a Schedule C. Also note the $11K will be included in your AGI. Claim your gambling losses up to the amount of. Second, the losses you report can’t exceed your winnings. Form 1040 Schedule A. The deductions only apply to gambling profits. In making its decision, the court relied in part on the testimony of a gaming industry expert who testified on behalf of Coleman. citizens or resident aliens for the entire tax year for which they're inquiring. Also, keep detailed records of the gambling losses you deduct for a period of at least five years. As long as you meet various qualifications — which most borrowers do — the IRS allows you to deduct the lesser of $2,500 or the amount you actually paid in interest on. Gambling Losses. You are allowed to list your annual gambling losses as an. S. Topic No. The only requirements are that you cannot report more losses than your winnings, and you must have records to support your claim. For federal purposes, you can no longer claim an itemized deduction for job expenses and certain miscellaneous deductions that were subject to the 2 percent of FAGI limitation. You can only deduct your gambling losses once, not twice. In other words, you cannot claim losses that exceed your total winnings. I just rounded to an even number, $10k, for the sake of the post. One tax reform-related change relevant to gambling is this: Because you must itemize gambling losses, it won't help if you don't have sufficient overall deductions to. You must include the U. For 2019 federal tax purposes he is eligible to claim an itemized deduction* based on the $345 amount repaid. Don't ever feel like you have to pay the IRS more tax than you actually owe. You would typically itemize deductions if your gambling losses plus all other itemized expenses are greater than the standard deduction for your filing status. You must itemize all your deductions to deduct your gambling losses on your tax return.