+1 what Eddie said.
Do you have a closeup photo of the pin in his shirt directly under his tie? I ask to see about the detail in which the pin is painted. After looking at the images, it occurred to me that the medal pinned to the jacket is subliminally prominent, as is the detail on it. If someone was going to forge such a painting, then putting something in the painting tying it to that Detroit team would key to getting a baseball collector interested. Without similar detail on the pin, then I'd infer that the 'extra detail' on the medal was intentional, a collector would be wanting to see that.
It reminds me of paintings found in courthouses depicting judges and such. after his playing days Thompson was a US Marshal, and he served as a bailiff in the federal courts there in Detroit. The painting could have been done in the early 1900s just as easily as thinking it was from 1887 or 1888. Are there similar paintings somewhere of other players from that team? It could have been painted later from a photo...
Asking about that portrait here was a good first step, but I think you need several more steps and obtain solid provenance before buying that. And it partly depends on how dear $75k is to you, how fanatical you are about Detroit baseball, and how driven you are in collecting stuff of 19th century Hall of Fame players. I wish you well with your research.
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