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One who follows
1986, Frederick D. Huebner, The Joshua Sequence, page 116:I had to concentrate on staying out of sight, yet close enough not to be stranded on the wrong side of a stoplight. I was working so hard at it that I didn't notice that the tailer had become the tailee.
2003, Philip R. Craig, A Vineyard Killing, page 74:When the car entered the traffic circle I followed after it, the tailed now tailing the tailer. The car's occupants, sure now that they'd been spotted, sped off ahead of me along Dodgers Hole Road.
2012, Henry Kane, Don't Call Me Madame:he became aware that he was being tailed. ... turned the action around and tailed the tailer, and then realized that the tailer had not been tailing him
Occupational title
2003, Dictionary of occupational titles, Claitor's Law Books and Publishing, page 1385:TAILER (mine & quarry) 930.666-014 / tailer (woodworking) 669.686-034
Cattle handler
2012, Lennie Wallace, Bow aves in the Bull Dust, page 111:Tailing is a kind of baby-sitting, only you baby-sit cattle. It is the tailer's job to hold the quiet — or relatively so —— cattle in a handy position at a creek junction or on a river flat, while the more favoured musterers scout out for more cattle.