Before the death of Queen Elizabeth I, Shakespeare was primarily recognized as an Elizabethan author. Once the Queen was dead in 1603 and James I claimed the throne, Shakespeare’s character, social position, and works underwent significant changes, making the Jacobean Shakespeare distinctly different from his Elizabethan one. One of the major themes in Shakespeare’s plays during the early Jacobean period is the general uncertainty regarding the new political stances and the future of England ruled by James I__ an uncertainty that bears a striking resemblance to the death of Queen Elizabeth II in 2022. As new historicists claim, the textuality of history as well as the historicity of a text have both been of prime significance for long. Although the new historicist approach is applicable to any type of text or discourse from any period of time, Louise Montrose and Stephen Greenblatt have mainly used it to examine the Renaissance Literature of the 16th Century England. This paper aims to apply a new historicist approach to three early Jacobean plays of Shakespeare; Measure for Measure (1603), Timon of Athens (1605), and King Lear (1605), through which the element of uncertainty has been focused on, just as well as the mutual effectiveness of the eventfulness of the era and Shakespeare’s plays on one another. It seems that not only did Shakespeare always base the main framework of his plays on a critical reflection of contemporary political events and dubious instabilities, but this type of reflective ideation sometimes even influenced the political and social events around him. He also seems to have been able to exempt himself of the potential government penalizations of the criticizing authors through his genius.