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…)
So, people compare stealing 2 million dollars to over inflating real estate to one of the largest banks in the world. Said bank lends the money anyway and gets repaid per the loan agreement in full plus expected interest. Just wow. Maybe you all can explain how lost money in the second scenario.
@George Romey — “What about… what about… what about…” Buddy, I said, “greater accountability, large and small, top and bottom, left and right, all the above…” not, here’s a false equivalence… let’s all get distracted by some logical fallacy… LOOK OVER THERE! *poof*
@ George — Right, and said person who is a serial committer of such frauds (and FAR FAR worse) now tries to pin absurd charges for the same on his enemies. Let’s see, doing something criminal to ripoff a big bank (or the voters of states like Georgia) for millions vs doing (apparently) nothing to get a mortgage to provide a home for a niece. Yeah, not exactly the same thing. That’s alright, the guy at the top will either be carried out in a box or cuffs before all is said and done. Probably a box following one-too-many Big Macs. Just imagine the stench.
Guess this answers the question if SWA has a internal audit dept…the paper voucher scam probably overlaps with the year it also went without a CTO in order to…save money – before $1B loss. So now it’s $1.02B lol.
Why do trolls have to bring politics into a theft by an employee? These sad trolls have to get some sort of political dig into just about everything posted.
@Win Whitmire — Oh, please. If it has to do with people, money, power, and culture, it’s all politics. As Capt. Lucky said recently at Cranky Flier, “politics came for aviation, not the other way around.” Those, like yourself, who shout ‘no-politics’ the loudest are often just rooting for their own ‘side’ to prevail in the comments, anyway. So, why not contribute on-substance, rather than attack method. C’mon, bud.
Chicago school teacher? Say no more.
@Coffee Please — Yeah, like, I’d much prefer a New Brandeis approach to the Chicago School… oh, you weren’t talking economic theory, were you… ah, just disparaging that city, because… you know… *DOG WHISTLE*
Old Military Saying: “If it’s measured, it’s done.”
Apparently, the vouchers were not reflected in someone’s budget; therefore, not monitored.
@ 1990. “It’s all politics” for you (“you be you”) doesn’t mean life is for the rest of us.
@One Trippe — Keep your horse-blinders on. Good call.