What did your boss do last night?

If he or she is anything like the execs on this list, you may want to check your company’s checking account.

A disturbing number of corporate spendthrifts have racked up astronomical bills for outrageous expenses on their firm’s dime — including multi-million-dollar toga parties in the Mediterranean and weekend retreats that probably cost more than what your entire mail-room staff made last year.

Finance departments beware – Here are some of the most recklessly extravagant corporate spenders:

1.  Roman-Style Excess

In 2005, Dennis Kozlowski, chief executive of Tyco International, a security systems company, was jailed for stealing $600 million from the firm and its shareholders. However, in the years leading up to his conviction, he had a whole lot of fun.

The most glaring example of Kozlowski’s fraudulently funded extravagance was a $2 million weeklong birthday party for his wife on a Mediterranean island featuring Roman-themed dancers dressed in togas and a performance by Jimmy Buffett.

“Guests arrive at the club starting at 7:15pm,” a memo sent to the party’s planners read. “We have a lion or horse with a chariot for shock value…Big ice sculpture of David, lots of shellfish and caviar at his feet.”

2. Strip-Club Spending Spree

One evening during Oracle’s OpenWorld tech conference last year, when many Oracle employees were prepping presentation slides and exhibition stands for the next day, one Oracle staffer named Jose Manual Gomez Sanchez allegedly used his company-issued American Express card to charge a whopping $16,490 worth of “entertainment” at a local strip joint.

Perhaps the most shocking part of the fiasco was the fact that two nights later, Sanchez had the gall to return to the strip club and use the same card to ring up another $17,050 in charges.

Fittingly, the strip club offers discounts to OpenWorld convention-goers.

3. The Post-Bailout Bash

This one might sting a bit. In September 2008, less than a week after AIG received an $85 billion bailout from the federal government, a group of the insurance giant’s top brass enjoyed a week-long retreat at the St. Regis Resort in Monarch Beach, Calif., replete with banquets, golf outings and, of course, lavish spa treatments.

After all was said and done, the tab totaled $440,000 including $23,000 for the spa. “They were getting their manicures, their pedicures, massages, their facials while the American people were paying their bills,” one House committee member famously said at a hearing condemning AIG’s ill-timed jaunt.

4.  Adultery, Christmas Tree, and a Shopping Spree

In 2003, an investigation into the over-the-top spending habits of Kmart’s CEO, Charles “Chuck” Conaway, found that Conaway had used company funds to cover personal trips to Vegas, nannies to watch his kids and home improvements, including an $82,000 fence, snow removal and dismantling Christmas trees.

Conaway’s improper use of company money even revealed a history of adultery as records showed that he charged Kmart for $15,000 worth of dental work for his wife, while also letting a vendor pay for a trip to Asia for him and his girlfriend. Talk about two-timing.

5) The Medieval Misappropriation

A crossbow. Yes, a seemingly intelligent former Executive Director of a local Habitat for Humanity used his organization’s credit card to finance, among other things, a crossbow. In total, the employee cost Habitat more than a $100,000 in charges related to his Gulf Shores condominium, his personal vehicle and his, um…medieval hunting habits?

 

Next Steps:  Imagine a world where your employees show up on time, work smart and deliver results for your small business day in and day out. Not there yet? Sign up for the weekly Small Biz Ahead Newsletter and we’ll send you the best science-backed strategies on managing productive, happy employees—including tips on how to get them to show up on time!