Federal Income Tax Archives

Prepayment: to Deduct in Year 1 or Year 2?

Say you are an accrual method taxpayer and you hire someone to provide a service to you in year one, the service is to be provided to you over a twelve month period, and you prepay the person for this yet to be provided service. When can you claim a deduction for this prepayment? The…

Bankruptcy Filing Does Not Prevent Innocent Spouse Relief

There are often times when different government agencies with different clients and missions are at odds with one another. This is frequently true when it comes to the IRS and the bankruptcy trustee. The IRS is tasked with protecting the government fisc. The bankruptcy trustee is tasked with protecting the estate for the benefit of…

IRS Says When a Grape is No Longer a Grape

The tax law is filled with artificial distinctions and deadlines that often don’t match up with the way businesses actually operate. One area where this is particularly true is in the realm of capitalization. Capitalization rules allow taxpayers to calendar expenses and treat them differently depending on the phase of a project or manufacturing process.…

One Ticket or Two? Withholding Tax on Small Lottery Winnings

Winning the lottery can be a dream come true for many, but it can also trigger a number of tax-related complexities. This includes everything from income tax on the sale of lottery payments to substantiating lottery costs and losses. The IRS frequently challenges these issues on audit. One of these complexities arises when it comes…

Sale of Lottery Payments: Capital or Ordinary?

The IRS is always waiting for taxpayers to have windfalls as the tax on these one-time events is significant. Lottery winnings are no exception, as they are treated as income from gambling and subject to ordinary income tax rates, which can be as high as 38% or more depending on the amount won. But what…

Court Preempts IRS by Taking Taxpayer Property

In some cases, courts may take shortcuts to ensure that justice is served. While these shortcuts can be effective in obtaining the desired outcome, they can also raise concerns about fairness and due process. One such case is United States v. Spangler, 224 F. App’x 890 (11th Cir. 2007), where a trial court ordered the…

Navigating the Taxability of Defamation Awards

The taxability of compensation for personal injuries unrelated to lost wages or earnings has been a topic of uncertainty, especially after the Murphy decision. The IRS may request the Supreme Court to resolve this issue if it is not successful in the upcoming rehearing of Murphy. Recently, the Ninth Circuit Court of Appeals solidified its…

Can the IRS Collect Additional Taxes After Tax Restitution Is Paid?

In the case of Creel v. Commissioner, 419 F.3d 1135 (11th Cir. 2005), the IRS attempted to collect additional taxes, penalties, and interest from a taxpayer even after his criminal restitution obligation for the very same tax had been paid and satisfied. The district court had ordered the taxpayer to make restitution to the IRS…

Referrals/Leads Group is Not a Tax Exempt Entity

The tax laws in the United States provide for several types of tax-exempt organizations, including charities, social welfare organizations, and business leagues. In Private Letter Ruling 200709070 the IRS has brought attention to the requirements for organizations to qualify as a tax-exempt “business league.” The ruling denied tax-exempt status to a referral/leads group on the…

Video Poker Cannot Qualify as Professional Gambling

As technology and computers advance, there are more and more activities that put us, as humans, against computers. We, as humans, are in the position of having to game or strategize how to manipulate or beat computers to produce desired results. While it is not pointed out generally, whole industries are focused on doing just…