I spent a few years in big global corporate world for a consumer products company. Due to acquisitions, multi-national locations, and being around for nearly 200 years means thousands of entities and an unimaginable number of tax filings.
Would the global head of tax quip they are under audit all the time? Of course and they would technically be correct.
With Trump, as with most all things Trump, people conflate a lot of different happenings to try and paint unique, oft misleading takes on the routine.
Trump has had several famously failed real estate deals, the most known being the casinos. Depending on which tax years one pics, those failed deals and subsequent losses wipe out his other income. But these become quite hard for the layman to follow due to the LLCs and partnerships, which ARE routine in real estate projects (unlike the Biden LLCs which are not as usual).
Another audit stems from the Trump Chicago project which opened in 2008. One can imagine that was not an opportune time for a luxury residential property to come online. In these deals, investors, owners, operators, residents, lenders all have different types of holdings through different entities - again all very standard. I imagine Trump participated in several different manners including a likely licensing deal on his name separate from owning several of the units like having an interest in the property amenities, parking, having some ownership in the partnership performing the construction management, maybe a separate investment for the land, separate for the development of the tower, maybe an interest in a partnership that brokered the sale of individual residences.
Trump claimed a substantial deduction for his original investment then other deductions later on related investments. The question from the IRS was whether this was a double-dip as Kansas Kid alluded to. However, it's not just likely but highly probably that alleged double-dip was related to write-offs of related, but separate investments in the project that rolled up to Trump. As a simple example, I invested in an entertainment venue that has a real-property interest. I have been offered opportunities to invest in the concession operations of the venue and an overall company that owns multitalented venues. If the entire thing goes tits up, then I have 3 different losses that to a rando on the webs looking at flown-the-coop's illegally released returns may conclude the IRS is right and I scammed them.
If it turns out I sue the IRS for releasing my information illegally and I also ask to resolve their claims I wrongly took the deduction, we may reasonably reach a settlement that also ends their audit of my losses and compensates me for their violation of law. It would be incorrect to assume that it was nefarious for them to drop ongoing audits and agree not to audit those years as they have already "tainted the pool" with their nefariousness in releasing the returns in an attempt to influence my business and personal reputation.
That's a ton of words to say that it is simply wrong to conclude the overall actions by the IRS regarding Trump were routine. People then lump in other actions taken by state agencies regarding the leak return to then paint Trump, his family and his businesses as perpetual tax cheats. They are not.
I am certain I may have gotten a minor detail or two not quite right but the overall picture is correct be my understanding.