The Bible is a religious canon but a good literature as well. Concerning the biblical ambiguity, can literature support or criticize theology? What is questioned is all about the academic role and influence of the English language and literature, and further about the literary criticism. Applying the syntactic thinking to contrasting a variety of sentences and the major words, this microscopic case study is to try to find more criticism to the structure, meaning and background of Matthew’s Beatitudes in the Sermon on the Mount of the English Bible. My version of Matthew’s Beatitudes, the extracted findings by the syntactic thinking for the questions raised, and eventually the induced conclusion about the above issues are ventured to pursue a kind of proposition. The analysis shows many syntactic findings resulting in the conclusion that concerning the biblical ambiguity literature independently precedes and thus can support or criticize theology. In such a way that this case study proves mostly through the digital humanities as a methodology, this approach to the English Bible by the English language and literature is strongly commendable for a literature-based non-confessional religious education particularly in Korea where it is very rare but fair. This literary research further insinuates that it would be also further induced other than just only from the Bible up to a more generalized theory applied to all kinds of religious canons including Confucianism, Buddhism, etc. So strongly recommended is such a policy of practical religious education for the Ministry of Education in Korea.