We explicitly study how jet substructure taggers act on a set of signal and background events. We focus on two-pronged hadronic decay of a boosted Z boson. The background to this process comes from QCD jets with masses of the order of m_Z. We find a way to compare various taggers within a single framework by applying them to the most relevant splitting in a jet. We develop a tool, TOY-TAG, which allows one to get insight into what happens when a particular tagger is applied to a set of signal or background events. It also provides estimates for significance and purity. We use our tool to analyze differences between various taggers and potential ways to improve the performance by combining several of them.
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