Okay it wasn’t as brazen as the post title suggests. But yes, it’s a real life datapoint of asking for an upgrade (that was probably deserved) and getting it!
Back at the end of January, when AA opened up premium award space to Europe pretty widely, I jumped on it to book a business class class ticket to Ibiza, SFO-JFK-LHR, LCY-IBZ as part of a summer Europe trip. My friends were going on the same trip, so I encouraged them to do so as well. Except for the first statement on their Citi AA cards hadn’t closed yet so they didn’t quite have the miles!
Space started to dry up over the next few weeks, so by the time that their statements closed and the miles posted, availability was a bit more limited. The boyfriend managed to grab the same itinerary as me fully in business, but the girlfriend could only get SFO-JFK in First, JFK-LHR in Economy, and LCY-IBZ in Business. I felt super bad that she was spending more miles (62.5k vs 50k), not sitting with her boyfriend for the two longhauls, and was stuck in Economy for JFK-LHR. The AA agent told her she would have top upgrade priority as a voluntary downgrade, but I doubted that as I don’t think there is a similar system as United, where you actually DO have top upgrade priority if you’ve paid the miles for the premium cabin but are in a lower cabin.
I recommended that they wait and check availability everyday, especially as the date got closer. I also set up a bunch of ExpertFlyer alerts so we could be alerted if space ever opened up.
Nothing had opened until a week before the flight. That leg was Saturday, and loads looked pretty low, and Thursday and Friday had both opened up seats on the exact same flight. But got to Friday and they still hadn’t opened up a seat for that Saturday flight!
I checked ExpertFlyer again Friday noon about 14 hours before the flight and ExpertFlyer was showing there was only 1 Business class seat left and none available for awards. Perhaps AA had already run through all their upgrades and now there was only one business class seat left. Now I was feeling pretty bad about my advice. I told them to ask at check in to see if there was an upgrade as she had already paid for a First Class award ticket and try her luck, but was feeling somewhat doubtful.
I show up at the airport to check in, where I found my friends. They said that as they checked in, she asked if she could be upgraded next to her boyfriend on that segment as she already had paid the First Class price but was stuck in Economy. The agent looked at his/her screen and was happy to do it! And when the boyfriend went to check the seat map, there were at least 4-5 seats left in business.
So lessons learned: obviously it’s better to book the cabin you want in the first place, but it’s possible to get that upgrade if it is a reasonable request and you ask nicely, such as getting the cabin you paid for in the overall award. AA may not necessarily reason award seats last minute, and their ExpertFlyer bucket information may also not be correct last minute.