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This article came out a couple years ago in a news column. We've learned here to never say never, but how about "It's not very likely"...the more we discuss these, the easier it seems to be able to dispel a rumor though. In this case bought by a high school would make it one of the school guns...I should think.
Antique rifle tells an American tale | Rappahannock News
Unfortunately, the article contains several errors, to wit: The "school guns" are modified carbines, NOT "cut-down" rifles (as in sawed off the barrels) and TR's Rough Riders did NOT use M95 Winchesters. But, it's a good story and a nice counterpoint to the mass shooting tales.
I would expect much of the detail was dictated to the writer by the expert holding the Krag...
Most of that article is pure blarney and old gun salesman 'BS'.
On reflection, maybe he is a public school teacher or at least a college professor!
Or a fiction writer...