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I would like more information on what I drank today, January 30, 2020. It is marked bottled by Osborn Brothers, Oporto, which I am not familiar with as a House.

I picked up the bottle at a Christie's Chicago Auction probably in the 70's. The bottle had sediment, but not enough to be a vintage or crusting port. There was no IDVP sticker so either it was bottled outside Portugal or before the Port Wine Institute (1933). The Bottle has an embossed 1 Pint 9 Fl Oz. My guess is that it was bottled in the 20's or 30's.

The wine's color was a medium mahogany. The taste was like a rich 20 year old tawny, though probably a little bit sweeter. It was well received by my self and six others at lunch.

I am curious about the "Osborne Brothers". Are they related to The Osborne Sherry people? And, what style of port this was originally.

Welcome to TPF, and thanks for sharing the image and story.

As far as I can tell, I can see no immediate connection between the Osborn brothers (no 'e' on the end) who were active in Porto in at least the mid 19th century with the Osborne family producing sherry since 1772, though they could of course have been related. Note that Osborne (with an 'e') did produce port from 1960 (see label examples here), though I don't necessarily see any connection to the Osborn brothers here.

I had not come across the Osborn Brothers as a shipper before, but I could find two references; the first is in papers relating to the sale of wine by British merchants to the US (letter of 1846 including "Osborn Brothers" as signatories alongside other well known houses including "Geo. Sandeman & Co.", "Croft & Co." and many others), and the second is in "A Word or Two on Port Wine" (a pamphlet apparently written by J. Forrester and published anonymously in 1844 decrying various poor practices in port wine production - a fascinating read, see here) in which the Osborn Brothers are listed as the largest exporters of Jeropiga from Porto in 1843.

Regarding your bottle therefore I'm afraid I can add very little; we might be able to tell a little more regarding the age of the bottle if you could provide addition photos of the full and/or top half the bottle (the embossing might tell others more regarding date; I suspect that limits the age of the bottle, though not the wine assuming it was originally tawny). An interesting bottle, and glad it was enjoyable. Thanks for sharing the story.

The remainder of the bottle (15%?) deteriorated the next day, It lost its fruit and the flavor was only acceptable. The color was still a medium mahogany without new sediment. Same for the second day after opening when I finished it.

I have attached additional photos for better dating of the bottle. The bottle was brown and appeared to be mechanically molded in two pieces with the top probably attached because there was no seam there. There was a fully driven cork that came out unreadable with some letters shown. There was a lead capsule, with some paraffin wax over it that I had applied after I bought it at auction many years ago.