Rare collectibles have a way of bringing out strong emotions, especially when someone misses out on an opportunity that may never come around again. Even the closest families can end up arguing over who truly deserves an item that almost nobody can find.
This Redditor, an avid bourbon collector herself, attended a special Thanksgiving event where lucky participants had the chance to purchase highly sought-after bottles at their original retail price.
When fortune smiled on her and she secured one of the rarest bourbons available, her brother-in-law immediately claimed it belonged to him because he had originally planned to attend before work got in the way.
The disagreement has lingered ever since, with both sides convinced they have the stronger argument. Read on to see what happened.
A bourbon collector’s rare raffle win sparked a family feud over who truly deserved the prize
From a third-person perspective, the OP appears to have acted consistently with her own understanding of the situation.
She was already considering attending the bourbon event because she is a collector herself and knew the raffle offered a rare opportunity to purchase a bottle of Pappy Van Winkle at retail price. When her brother-in-law had to work, her sister invited her primarily for company.
Although her sister was clearly attending as his representative, the OP viewed herself as an independent participant pursuing the same opportunity for her own collection. At no point did she agree to purchase a bottle on his behalf or promise to surrender anything she won.
When her number was drawn early enough to buy the coveted bottle, she simply exercised the opportunity that came with her own raffle entry.
From the brother-in-law’s perspective, however, the situation likely feels very different. He had been excited about the event for weeks, only to lose his chance because of work obligations. Since his wife attended specifically to stand in for him, he may have unconsciously extended that assumption to the OP as well.
Watching someone else walk away with the exact bottle he had dreamed of owning and someone who arrived alongside his designated stand-in could understandably create a sense of “that should have been mine,” even if no actual agreement supported that belief.
Emotionally, disappointment often feels like injustice, especially when rare collectibles are involved.
Behavioral economist Daniel Kahneman, whose work on decision-making transformed modern psychology and economics, described how people experience losses more intensely than equivalent gains, a principle known as loss aversion.
Research consistently shows that people feel the pain of missing out on something highly valued more strongly than the pleasure of acquiring something of equal value. That psychological tendency can make near-misses feel deeply personal, even when the outcome was determined fairly.
That insight helps explain why “Pappygate” has lingered. The raffle itself was random. Every participant received an independent number, and no one was guaranteed an opportunity to purchase the prized bottle.
Had the brother-in-law attended, he might just as easily have drawn a later number and missed out entirely.
His frustration stems from imagining the best possible alternate reality, one in which he attended, received the OP’s favorable draw, and secured the bottle, while overlooking the many equally possible outcomes where he still would have gone home empty-handed.
Psychologically, people tend to compare reality with the most favorable hypothetical rather than the average likely result.
Ultimately, this disagreement seems less about ownership than about assumptions. The OP never believed she was representing anyone but herself, while her brother-in-law appears to have assumed everyone accompanying his wife was effectively participating on his behalf.
Neither interpretation was completely unreasonable, but only one was actually communicated. If there is a lesson in this story, it is that rare opportunities make implicit expectations especially risky.
A simple conversation beforehand, “If either of us gets the Pappy, whose is it?”, would probably have prevented a years-long family joke.
In the absence of that agreement, though, it is difficult to argue that she “stole” something that was awarded to her through a fair raffle and purchased with her own entry.
Here’s the comments of Reddit users:
These Redditors said the sister was his proxy, so OP owed him nothing
This group argued OP attended as a collector and won the bottle fairly
This commenter believed the brother-in-law was acting out of jealousy
These users felt OP should have prioritized kindness and let him have the bottle
Do you think she was right to keep the bottle she fairly won, or would giving it to her brother-in-law have been the kinder choice?
