Loopholes

When we enter upon a new Administration, we wonder at the shape of things to come. But surely since 1916, we have never had an incoming Administration promise us a repeal of the income tax and the reestablishment of the import tariff as the principal source of Federal funding. I would not, however, immediately cease to follow the proceedings of the US Tax Court.

Is student loan forgiveness taxable? Yes. No. Maybe. Sometimes. It primarily depends on the student loan forgiveness program. But like everything else with student loans, there are a number of other factors at play. Why make it easy when you can thoroughly confuse taxpayers, federal student loan servicers and financial planners for years to come? Keep reading to learn when student loan forgiveness might be tax-free and how to prepare your clients for taxable loan forgiveness.

John Anthony Castro is a colorful character. He entered several Republican primaries seeking the Presidential slot after failing to win the primary for a Senate seat representing Texas. He sued to have our once and future President Donald Trump be removed from the ballot on Fourteenth Amendment Section 3 grounds. As we can easily infer, those suits went nowhere. But more than anything, John Anthony Castro was a tax guy with a virtual practice with locations in four cities. Not anymore. Now he is resident in a Bureau of Prisons facility – the Federal Medical Center Fort Worth. On October 30, 2024, Judge Terry Means sentenced Castro to 188 months in prison, followed by one year of supervised release and restitution of $277,243, following his conviction on 33 counts of “Aiding and Assisting in the Preparation and Presentation of a False and Fraudulent Return." Does the sad story of John Anthony Castro hold any lessons for us? Perhaps.

No holiday break for US Tax Court, as fresh developments arise, and some old doctrines need reenforcing. As usual, we've got both common problems and arcana on the radar, with one potential blockbuster.

There are roughly 42.7 million federal student loan borrowers as of Q4 2024, creating an opportunity to provide additional insight to your clients beyond tax preparation. By leveraging certain tax and repayment strategies, you can help your clients reduce their tax liability and lower their student loan payments in one strategic swoop. Here’s how.

Just a few new developments out of United States Tax Court in November. Technical issues predominate in this short working month.

In the prior article "Tax Trends in M&A and What It Means for Your Clients," we had discussed certain techniques to, e.g., maximize net operating loss (“NOL”) and interest expense deduction utilization in the context of M&A transactions. This article examines certain additional strategies to monetize expiring, latent, or otherwise disallowed tax attributes.

On the website for Axium Wealth, Charles Dombek tells us that: “Most CPAs are historians that tell their clients how much they make, how much they owe, when and where to file their taxes, and oftentimes how to write large checks at the last minute when you least expect.” When it comes to Axium, though: “We help clients recover dollars they unnecessarily pay in State and Federal income taxes.” Axium also helps clients diversify capital into off-market passive real estate and alternative investments. Before Axium, there was The Optimal-Financial Group LLC. Of course many of the readers of Think Outside The Tax Box are CPAs, or EAs or others who both help their clients be compliant and advise on ways to minimize their liability. When I was practicing I would call the things I might suggest my “bag of tricks.”