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TeachMeFinance.com - explain Tailer historic definition... Tailer -- A colloquial appellation for a small speculator who tries to follow a large speculator or group of speculators in his dealings. Copyright © 2007 by Mark McCracken, All Rights Reserved. TeachMeFinance.com is an informational website, and should not be used as a substitute for professional financial or legal advice. TeachMeFinance.com and its owner recommend consultation with a professional financial advisor prior to any investment or financial decision. Please read our disclaimer.