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    Well, certainly +1 for verifying the authenticity of the images. It doesn't do much for adding addtional proof, but maybe it is the only that can be done. I was just hoping that such a fun-story would create or leave some sort of trace in history over time. After all, if it is true, there is at least one person that could confirm it.
    – BmyGuest
    Commented Sep 25, 2020 at 18:02
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    @BmyGuest perhaps that one person is Bill Gates himself, and he's disinclined to admit it? Commented Sep 25, 2020 at 20:51
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    @MarkRansom the use of the photo may as well be unauthorized by Bill Gates. Graphical designers behave sometimes like this.
    – fraxinus
    Commented Sep 26, 2020 at 6:40
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    A statistical analysis of the geometric closeness of the silhouettes could quantify the evidence that they are associated. If they were both available at an arbitrarily high resolution and they continued to match perfectly, that would make it asymptotically certain that the similarity is not coincidental. As it is, given that they match within some finite error, one could determine that the Outlook silhouette is more similar to this mug shot than to X% of frontal head-and-shoulders portraits from a large photo library. If say X% = 99.99%, this would be very strong circumstantial evidence.
    – nanoman
    Commented Sep 26, 2020 at 7:55
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    My intuition from visual inspection of the last comparison image is that the evidence is very strong, because the Outlook silhouette closely matches many specific shapes that would vary from one portrait to another: the width and slope of the shoulders, the right shoulder being slightly higher than the left shoulder, the extra-wide collar, and about a dozen protrusions/indentations in how the hair falls around the head. There are only 3 free parameters in the match (scale, x and y offset -- looks no rotation is needed).
    – nanoman
    Commented Sep 26, 2020 at 8:06