Originated from a miniature online bookseller to a massive superstore company raking in $75.5 billion in the first fiscal quarter of 2020 despite the surge in COVID-19, Amazon is arguably a frontrunner in e-commerce over the course of its spectacular 25-year history. This paper conducts a critical assessment of Amazon’s strategy in multi-dimensions, evaluating its initial tactics, the subsequent diversification, how the acquisition could fit into its strategy, and the strategic challenges facing the Amazon Empire.