To be fair to Mr. O'Brien, he entered the book business in 2003, when economic prospects were much brighter. Nonetheless, this was still a very poor choice. Mr. O'Brien is a lawyer. He certainly should have known better. John O'Brien graduated from the New York University Law School in 1992, and quickly went to work for Sullivan & Cromwell, a major New York law firm. In 2001, he was named a partner. Partners in large New York law firms make a lot of money, at least by ordinary people's standards. His tax liability was substantial, but only because the amount of money he was raking in was even greater. Somehow, he thought the IRS wouldn't notice.
According to charges filed against O'Brien, from 2001-2008 he earned $10.8 million in partnership income. He readily knew this because his firm sent him "K-1" forms listing his share of partnership profits (these are similar to the W-2 forms you receive for earned income). What Mr. O'Brien surely must have also known, and which makes all of this so baffling, is that the law firm would have sent copies of these forms to the IRS too. A graduate of Princeton University and New York University Law School should have recognized the danger, the almost inevitability.
O'Brien could have paid his taxes, but according to the U.S. Attorney's office, "Instead, O’Brien used the funds for various personal expenses, including the purchase of a weekend home, international travel, and the funding of a rare books business." Apparently, the biggest share went to the rare book business. He formed Hudson Street Books of New York in 2003, and apparently pumped a few million dollars into it. The firm described its specialties as "music, the visual and performing arts, history, religious studies, and related fields." Hudson Street Books appears to have closed down in 2009, which was also the year O'Brien departed Sullivan & Cromwell, evidently because he was facing major scrutiny from the IRS by that time.
In a prepared statement U.S. Attorney Preet Bharara couldn't help leveling a few jabs at Mr. O'Brien's behavior, stating, "John O’Brien went to work every day at a prestigious law firm where he advised clients on how to comply with the law at the same time that he was knowingly breaking it. He thumbed his nose at the IRS to fund an even more lavish lifestyle than his generous income permitted."