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Eric I find this to be an interesting topic. To even have a remote chance of accurately determining whether or not a card has been trimmed, one would have to obtain the machine(s) used to cut the card. After the machine was obtained, one would have to cut a card with the device and compare the cards' striation marks to the striation marks on the card in question. This comparison would have to be done under a microscope. At this point, you MIGHT be able to determine whether or not the striation marks on the card in question are the same as those on the card you've just cut. Does this sound ludicrous? You bet! Why?? Well, although this is a valid method of examining a card for evidence of trimming, it is doubtful that the original cutting machines are still in existence. In addition, as the cards age, the paper begins to deteriorate (particularly along the edges), making it even harder to examine the striation marks. You would also have to take into account how sharp (or dull) the cutting blade is. There are a lot of factors to consider when it comes to card trimming. I have seen dealers at card shows pull out a magnifier, observe paper fibers sticking up, and proclaim that the card has been trimmed. This is NOT an accurate way to determine if a card has been trimmed!!
You might be able to determine if a card was trimmed by a pair of scissors by looking for a crimp mark on the card. This should be done under a microscope. As the pair of scissors first comes down on the card, it has a tendency to pinch the cardboard and may leave a crimp mark.
I too have seen cards from age old collections where the cards are a variety of sizes and have been stored in a cigar box for years. It is doubtful that the cards were ever trimmed. The quality control back then was probably not as strict as it is today. I'm sure those manufacturers were more interested in selling a product and less interested in the long term value of the cards.
As for the grading companies, they probably use a sizing template and if the card falls short of the allowable tolerance, they assume (for business reasons) that it shows evidence of trimming. In reality, it is virtually impossible to determine whether or not a card has been trimmed. And so, the card companies are playing it safe. If you're not sure, then why not err on the conservative side? I admit, however, that it is inconsistent for a company to say at one time that the card looks trimmed and in a subsequent submission say that it's not. If I received a card from a company that had been marked "evidence of trimming," then I'd ask for specific proof. The fact that the card is shorter than the standard dimensions is only one aspect to consider when trying to determine whether or not a card was trimmed.
Bottom line is....buy what you like.