Lorillard, formerly the third-largest tobacco company in the United States, provides a fascinating case study in corporate finance and strategy, particularly within a heavily regulated and ethically fraught industry. While Lorillard no longer exists as an independent entity, its financial history reveals crucial insights into valuation, mergers and acquisitions, and adaptation in the face of declining demand. Before its acquisition by Reynolds American (now British American Tobacco) in 2014, Lorillard’s primary revenue driver was the Newport cigarette brand, a menthol cigarette popular among specific demographics. Its financial performance was marked by consistent profitability despite declining overall smoking rates. This was largely achieved through strategic pricing, brand loyalty, and cost management. Lorillard employed a “value pricing” strategy, positioning Newport competitively while maintaining healthy margins. A significant aspect of Lorillard’s financial story is its relationship with the Master Settlement Agreement (MSA) of 1998. This agreement between major tobacco companies and numerous state attorneys general obligated the companies to make annual payments to the states to cover healthcare costs associated with smoking. The MSA heavily impacted Lorillard’s financial planning, forcing them to allocate substantial resources to these ongoing payments. This placed a constraint on their ability to invest in new product development or aggressive marketing campaigns outside of limited channels. Despite these limitations, Lorillard actively explored alternative avenues for growth. They ventured into the e-cigarette market with the acquisition of Blu eCigs in 2012, aiming to diversify their product portfolio and capitalize on the emerging vaping trend. This move represented a strategic bet on future growth as traditional cigarette consumption continued to decline. However, Lorillard’s foray into e-cigarettes proved less successful than anticipated, facing stiff competition and evolving regulatory hurdles. The 2014 acquisition of Lorillard by Reynolds American was a complex transaction driven by both strategic and financial considerations. To avoid antitrust concerns related to market concentration, Reynolds American was required to divest some of its brands, which were subsequently acquired by Imperial Tobacco. This multi-party deal exemplifies the intricate financial engineering often involved in large-scale mergers and acquisitions, especially in highly regulated industries. From a valuation perspective, Lorillard’s profitability, strong brand equity (particularly with Newport), and consistent cash flow made it an attractive target for acquisition. The valuation took into account the MSA obligations, the potential risks and opportunities associated with e-cigarettes, and the overall market dynamics within the tobacco industry. Lorillard’s story underscores the challenges and opportunities faced by companies operating in industries with declining demand and significant regulatory burdens. Its strategic pricing, cost management, diversification efforts, and ultimately, its acquisition, highlight the key financial strategies employed to navigate a complex and evolving business environment. Although Lorillard no longer exists as an independent company, its legacy provides valuable lessons in finance, strategy, and adaptation within a controversial industry.