I used to work at a regional airline. The jet we used for our flight to the “big city” had 6 business class seats. The business class service was really good for a 2 hour flight. It included a full bar service, a hot meal, warmed bread basket, followed by a trolley with dessert and signature coffee. The good old days...

One of our regular travelers was a local business owner who was just… a slimy businessman (SB). He had a reputation for making a lot of money from some pretty shady deals over the years. We would roll our eyes when we saw him coming to the check-in counter because he would always name drop and ask for special treatment. He always used the business class check-in line even though he was usually in economy. He didn’t have frequent flyer status, but he was buddies with one of the airline executives and always let us know this fact when he checked in by making sure to tell us that he was good friends with Vice President Karen. He would always ask for free upgrades, extra baggage, not charging a change fee, last-minute discounts, etc. If he didn’t get what he wanted he immediately called VP Karen, who would usually then call us and approve whatever it was he wanted.

So one day SB checks in for his flight to the “big city” and of course name drops and asks for a free upgrade to business class because "I'm friends with VP Karen and said it would be ok." He was traveling on a discounted ticket that was not eligible for upgrade even if he did have an upgrade coupon, which he didn’t.

I informed him that he was not eligible for any upgrade on this ticket and gave him his boarding pass and sent him on his way. Of course he flips open his cell phone and immediately calls VP Karen. Within 2 minutes the phone at the check-in desk rings and it’s VP Karen authorizing me to override the policy to upgrade SB to business class with no upgrade coupon required “if there is room.”

The flight that day wasn’t that busy and only 1 person booked in business class leaving 5 open seats. I was really irritated but I begrudgingly put SB on the upgrade list anyways. He returned to the check-in counter and picked up his standby boarding card and gave me that smug “told you so” look. But then what VP Karen said clicked with me - “if there is room.”

The next passenger I checked in was a SUPER nice lady, big smile, friendly, please and thank-you, oh thank-you so much for checking my bags to my connecting flight, that’s so nice of you. I was taking my time and we were chatting a bit since it wasn’t that busy. She was a teacher going on a trip to see her family and it was her first visit with them in over a year and was going to meet her new little nephew for the first time. She was overjoyed just to have the time off to travel. I typed in a few things into the computer to make it look like I was checking something about her connecting flights and then said “Oh, you have been selected today to receive a free upgrade to business class.” She was shocked. “I’ve never flown business class in my life! This is so amazing!”

At that time we were rarely questioned if we upgraded someone without a certificate. Over the next 20 minutes I found excuses to upgrade four other passengers - one who worked for one of our top corporate accounts, one who was legitimately a frequent flyer, can’t remember the other reasons, but by the time I went to board the flight I had to tell SB that I was sorry but business class was full and couldn’t offer him an upgrade today.

The teacher I upgraded profusely thanked me again when she boarded with the rest of the business class passengers. Little did she know that it really made my day also!

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Thank you all for the votes and awards! I'm a long-time lurker but first time poster. This will encourage me to share more tales from the airport. I could probably write a whole book about the crazy Karens, the very good and the very bad staff, the non-rev trips... anyone who has worked in the airline world knows it is unlike any other job.

There were no repercussions to my actions. We rarely upgraded passengers randomly so it wasn't something that caught management's attention, and they mostly trusted our judgment on these things. But, like many customer service jobs I'm sure, if you were nice to us we would go out of our way to help you. If you were not nice to us, we would apply the rules very strictly. Our boss did watch baggage like a hawk though - if you printed more bag tags than the passenger allowance without collecting the excess fee it showed on your daily report and you would be asked about it at the start of your next shift.