There's no anchor on your button's front. Your second photo (as posted) shows the correct orientation. I see four intertwined letters, which are written in a font that was popular from the 1880s into the first 10 years of the 1900s. I see a letter I atop a T atop and S atop an R. Note that the R is the smallest letter, the S is second-largest, and the I is largest of the four letters.
Often, though of course not always, when you see a button with an interwined monogram which includes an S, that S stands for School. Similarly, letter I often stands for Institute. An R often stands for Regiment -- or Railroad. So, my "best guess" is that you've found either a School/University button, or a Railroad button, although it could be a County/City Militia Regiment button. I say "best guess" because I searched through all the Schools/Universities buttons, and Unknown/Unidentified buttons in the Albert book, and did not find a match. Being weary at that point, I did not search through every state's County/City Militia buttons... so that's your job.
