American Express's 1987 launch of the Optima Card — its first revolving credit card — was a strategic and financial disaster that nearly destroyed the company's premium brand positioning. The Optima card was marketed through existing AmEx charge card relationships but attracted a segment of cardholders who wanted revolving credit rather than the responsible charge card experience — resulting in credit losses that required over $1 billion in write-offs in 1992 and contributed to CEO James Robinson's forced resignation. The episode demonstrated that AmEx's premium brand did not automatically confer credit quality advantages and that revolving credit required underwriting discipline that AmEx had not developed.

James Robinson's "financial supermarket" strategy — acquiring Shearson Lehman Brothers (investment banking), IDS Financial Services (financial planning), Trade Development Bank, and other financial businesses through the 1980s — created a conglomerate that was capital-intensive, cyclically volatile, and culturally incompatible with AmEx's consumer payment brand. The strategy consumed management attention and capital that could have been invested in the core card business, and the eventual divestiture of most financial supermarket assets under Harvey Golub cost AmEx years of strategic clarity and billions in restructuring costs.

American Express maintained its premium merchant discount rate structure throughout the 1990s and 2000s without sufficiently investing in expanding merchant acceptance to close the gap with Visa and Mastercard — allowing the acceptance differential to become a meaningful deterrent for consumers considering AmEx as their primary card. The strategic error was treating merchant acceptance as secondary to cardholder economics rather than recognizing that acceptance universality is a prerequisite for cardholder value. The belated acceleration of merchant acceptance investment in the 2010s was necessary but costly in lost cardholder acquisition opportunity during the preceding decade.

American Express's exclusive co-brand partnership with Costco — which gave AmEx exclusive acceptance at all Costco locations and generated an estimated $80+ billion in annual card spending from Costco shoppers — was lost to Citibank and Visa in 2016 when AmEx refused to match the economics Citi was willing to pay for the partnership. The loss removed a major everyday spending category from AmEx's cardholder value proposition and transferred the spending of millions of premium consumers who used the Costco AmEx as their primary card to a competing Visa product, representing one of the most costly co-brand partnership losses in credit card industry history.

American Express was slower than Chase and Capital One to invest in digital-first cardholder experiences — mobile app functionality, real-time transaction notifications, instant virtual card issuance, and frictionless dispute resolution — through the 2010s, creating a perception among younger consumers that AmEx was a legacy financial institution rather than a modern digital-first brand. The digital experience gap contributed to the millennial acquisition underperformance that the post-2019 product revamp was designed to correct, representing a multi-year competitive disadvantage in the demographic most important to AmEx's long-term cardholder base renewal.