Introduction. This article focuses on the investigation of Boole’s theory of categorical syllogism, exposed in his book “The Mathematical analysis of Logic”. That part of Boolean legacy has been neglected in the prevailed investigations on the history of logic; the latter provides the novelty of the work presented.Methodology and sources. The formal reconstruction of the methods of algebraic presentation of categorical syllogism, as it is exposed in the original work of Boole, is conducted. The character of Boolean methods is investigated in the interconnections with the principles of symbolic algebra on the one hand, and with the principles of signification, taken from R. Whately, on the other hand. The approaches to signification, grounding the syllogistic theories of Boole and Brentano, are analyzed in comparison, wherefrom we explain the reasons why the results of those theories are different so much.Results and discussion. It is demonstrated here that Boole has borrowed the principles of signification from the Whately’s book “The Elements of Logic”. The interpreting the content of the terms as classes, being combined with methods of symbolic algebra, has determined the core features of Boolean syllogism theory and its unexpected results. In contrast to Whately, Boole conduct the approach to ultimate ends, overcoming the restrictions imposed by Aristotelean doctrine. In particular, he neglects the distinction of subject and predicate among the terms of proposition, the order of premises, and provide the possibility to draw conclusions with negative terms. At the same time Boole missed that the forms of inference, parallel to Bramantip and Fresison, are legitimate forms in his system. In spite of the apparent affinities between the Boolean and Brentanian theories of judgment, the syllogistics of Boole appeared to be more flexible. The drawing of particular conclusion from universal premises is allowable in Boolean theory, but not in Brentanian one; besides, in his theory is allowable the drawing of conclusion from two negative premises, which is prohibited in Aristotelian syllogistic.Conclusion. Boole consistently interpreted signification of terms as classes; being combine with methods symbolic algebra it led to very flexible syllogism theory with rich results.