Back in 2023 I wrote about a Southwest Airlines customer service agent at Chicago Midway who allegedly discovered the airline’s LUV vouchers weren’t just goodwill tools – they could be turned into money on demand.
One of the buyers in that scheme, a former Chicago Public Schools teacher, has been sentenced to a year and a day in federal prison for his role in the fraud.
Customer service agents at the airport can issue Southwest Luv Vouchers as compensation. One agent discovered he could do this even when there wasn’t actually a disserviced passenger.

The Midway agent and a former Chicago Public Schools teacher worked together, according to the indictment, to generate these vouchers and sell them for cash. The agent had the printing press. The teacher brought the buyers. In total about $2 million was alleged to have been stolen. The scheme lasted four months:
- The vouchers were $200 – $500 each
- That likely means creating about 50 fraudulent vouchers per day. Every single day, weekday and weekend, whether working or not.
- So it probably means generating even more vouchers than that per workday. Did this guy ever do actual customer service work?
In St. Louis, another Southwest employee was later caught with roughly $36,000 in stolen travel vouchers hidden in an airport locker – a smaller case in dollar terms, but the same structural problem. Once an employee realizes vouchers are effectively stored value with weak controls this becomes almost inevitable.


I’d think it a safe bet said teacher will get rehired by the Chicago school district upon being released from prison.
@ George — That seems fair given that Dear Leader received 37 felony convictions and was rehired. It won’t end so well for him next go round.
Steal $2M and you get one year and a day in the pokey. Seriously? I’m shocked more people aren’t doing this.
@George Romey — No one condones misbehavior, criminal or otherwise; however, yet again, your cynicism and nihilism are not the solution either. There must be greater accountability, large and small, top and bottom, left and right, all the above. But, inevitably, you’ll punch-down, regardless. Wouldn’t it be something if those with money and power were held to account, too? Hmm.
A year and a day results in a shorter sentence than a year. That’s because you get good time credit of 15% if your sentence is longer than 1 year. This results in 311 days in jail v 365.
@Thing 1 — As @Gene correctly points out, the fish rots at the head. Our President is the poster-child for the global criminal kleptocracy. (Just imagine, if it were someone from the other party…)