Taxpayer with his own funds bought a building 40 years ago that was titled in his father’s name. During that time until present, Taxpayer was operating a doctor’s office as a sole proprietorship out of that building. Despite all indicia of ownership, Taxpayer never took title.
Taxpayer’s father died 25 years ago and left all his property to his wife. During this time, Taxpayer continued to operate a doctor’s office out of the building. Years later, the Taxpayer’s mother died and her will left all of her property to be shared amongst the children (Taxpayer and Brother) equally. Brother of Taxpayer decided to file suit for the property.
The taxpayer decided to settle and pay a lump sum settlement of $100,000.00 dollars to Brother. The settlement discusses an agreement arising out of the Estate of Taxpayer’s mother between Taxpayer, individually, (he was operating a sole proprietorship), and Brother. Taxpayer took out a home equity loan (against his personal residence) to pay for the settlement.
Would the settlement be a deductible expense on the taxpayer’s 1040?