There has long been a tradition of scooping a hollow in the top of a whole Stilton cheese (either full sized or a baby) and adding port to it – “feeding” it daily.
I like Stilton, and I like port. Contentiously though, I think the two items should be enjoyed together but separately.
My theory is that 200 plus years ago, Stilton had to be transported, without refrigeration, from the makers to, say, London, in summer by stagecoach. UPS it was not, and could take a few days.
In the middle of summer this could cause the cheese to dry out and lose its beautiful creaminess which could cause consternation (and a financial loss) to the cheesemongers who had ordered it.
Port goes with Stilton and there is no doubting that, so maybe some clever chap devised using port to wend its way through the arterial blue passageways of the cheese to soften it and then got some gullible fashion setter to declare it “The In Thing”.
I can’t think of any other way the idea might have come about.
But I might be wrong?