O'Grady returned from Faro airport, Portugal - sans luggage - on 10 July. He flew via Heathrow with codeshare partner Finnair.
Even while transiting the London airport he could tell there were issues with luggage.
"I was just completely floored by how much luggage was in that baggage claim area. I thought to myself: 'I'm not super confident that my bags will even be transferred behind the scenes for tomorrow's flight,'" he told Insider.
O'Grady was right.
He said he spent over an hour at Raleigh-Durham International but the bags were a no-show. Without any update the airline apologised that the luggage had never been scanned through.
In spite of sharing the trip with 30 of his colleagues he was the only on who lost his luggage - both pieces.
Having been contacted with images of his lost cases, he thought it would be a simple process of being reunited with the luggage.
The American Airlines' customer service thought so too, providing he could go back to London:
"We suggest that you could head down to the airport to have this sorted out ASAP," wrote the airline.
Flabbergasted and a little annoyed - O'Grady shared the conversation via Twitter.
To add insult to injury the airline responded: "We've responded to your DMs. See you there!"
The exchange went viral, with passengers piling on to share their gripes of broken luggage and disbelief at the response.
O'Grady was eventually reunited with the case on 15 July, almost a week after the incident happened.
"I've traveled all around the world," he told Insider. "I've never seen anything like this."
In April, a US Department of Transport report found that nearly one in every 140 bags on flights operated by American Airlines were mishandled.
This is higher than the proportion of bags mishandled by most other airlines flying trans-Atlantic routes.
American Airlines was contacted for comment, regarding the odd exchange.
