Alphabet's decision to finance its artificial intelligence capital expenditures through the issuance of a $100 billion century bond represents a "massive bet" on a technology that is only three years old, according to economic strategist Hardika Singh of Fundstrat. The bond offering received 10 times more demand than available supply, prompting comparisons with historical issuers of century bonds, most of whom eventually faced significant challenges or outright failure. Singh noted that Alphabet's move contrasts sharply with past century bond issuers. "Alphabet itself is only 28 years old... yet it is making this enormous bet on AI through this $100 billion bond issuance," she stated, adding that previous century bond issuers tended to be older, more established companies she described as "the 'baby boomer' enterprises of their era." Singh cited historical precedents to illustrate the risks involved. JCPenney issued a 100-year bond in the late 1990s but filed for bankruptcy just 23 years later, leaving creditors with substantial losses. General Motors also experienced difficulties with long-term debt. This raises questions about whether such bond issuances signal a business model at its peak or one poised for growth. Singh believes the core issue is whether Alphabet can maintain its dominant position over such an extended timeframe. "The critical question is whether a company can continuously disrupt its own industry and reinvent itself? Because 100 years is indeed a very long time," she explained. Despite these concerns, the bond's overwhelming demand indicates investors haven't abandoned large technology companies. Singh acknowledged that while these firms may have lost their "cult-like status," the oversubscription demonstrates sustained market confidence in their ability to generate returns. Given big tech's substantial weighting in major indices, this has significant implications for broader markets. Singh questioned whether markets could continue reaching new highs if these key players - particularly in what she termed the "software stock dilemma" - fail to recover. For long-term bondholders such as insurance companies and hedge funds seeking high convexity, the ultimate success of this bond issuance depends entirely on Alphabet's ability to maintain its disruptive edge across future generations.