The paper looks at the problem of correlation of cognitive processes taking place in the person’s cognition with the syntactic organization of their speech. The speech of any individuum mirrors their thinking, and this is one of the ways they come to know their environment, acquire cognitive experience for building up their own picture of the world. In the process and due to communication, a human is shaped as an individual with a certain intellectual level of mind. The presented work is focused on syntactic peculiarities of the English-language verbal message, produced depending on the intellectual level of the virtual speaker. The topicality of the conducted scientific research consists in lingual and gnoseological need to penetrate into the cognitive-communicative essence of the processes of generating messages, and is motivated by the lack of serious scientific research of this problem. The objective of this paper consists in singling out a scientifically valid criterion for determining the intellectual level of a virtual speaker in the aspect of syntactic construction of sentences inherent to him. The starting point of this research was an assumption that there are certain typologically different structural sentence models, preferred by representatives of a certain psychological group of individuals. In our previous studies, it was established that in dialogue communication, simple sentences prevail among other structural types, while complex sentences take the third place in terms of use frequency with almost all speakers, regardless of their education level, social status, and cognitive abilities. According to our observations, a striking contrast can be seen in the native speakers’ use of complicated sentences, the grammatical status of which is not fully specified in grammar. The carried-out research specifies the concept of “complicated sentence”, and by means of comparative analysis of speech samples provided by the protagonists’ of three English novels captured at different stages of their lives, this type of sentence is determined as an indicator of the speakers’ cognitive peculiarities at the level of syntax. It is suggested that, in contrast to the surface representation, deep structures of human speech organization correlate with deep structures of human thought activity. Hence, a high intelligence level of an individuum is reflected not only at the level of adequacy of information perception, but also in the form of message representation and generation, namely, mainly in the constructions with a hidden deep structure of predication.