Bill Ackman Backs Microsoft (MSFT) Stock While TCI Exits After Decade-Long Hold

Table of Contents Microsoft (MSFT) shares surged on Friday following the revelation that hedge fund manager Bill Ackman’s investment firm, Pershing Square Capital Management, established a significant position in the tech giant as a “core holding” while simultaneously exiting its Alphabet investment. Microsoft Corporation, MSFT Shares traded at $424.81 by midday ET, representing a 3.76% gain. The stock peaked at $426.44 during the session, marking a 4.1% intraday advance. Meanwhile, broader market indices moved in the opposite direction, with the S&P 500 sliding 1.2% and the Nasdaq declining 1.4%. In an extensive 887-word social media post Friday morning, Ackman explained his rationale, describing Microsoft’s current valuation as “highly compelling” after sustained selling pressure that has pushed shares down 13% year-to-date in 2026 and 22% below their record high. The investment represents a complete portfolio swap — Pershing liquidated its entire Alphabet stake to finance the Microsoft acquisition. Ackman highlighted the company’s cloud infrastructure operations and commanding presence in office productivity applications as fundamental pillars supporting his investment thesis. Ackman’s enthusiasm isn’t universally shared. TCI Fund Management, managed by Chris Hohn and recognized as among last year’s most successful hedge funds globally, discreetly liquidated the bulk of its $8 billion Microsoft position — an investment maintained for ten years. TCI communicated its reasoning directly to investors: “We reduced our investment in Microsoft because the rapid progress in AI introduces uncertainty over Microsoft’s competitive position in the future.” This situation presents two highly respected investment firms analyzing identical circumstances and arriving at diametrically opposed investment decisions. Financial analysts are keenly observing which perspective will prove accurate. Microsoft CEO Satya Nadella appeared in an Oakland courtroom this week, providing testimony in Elon Musk’s litigation against OpenAI. Microsoft has channeled approximately $12 billion into OpenAI across seven years and currently maintains a 27% ownership stake valued near $230 billion. Musk’s lawsuit aims to dismantle this partnership, creating genuine strategic concerns for Microsoft’s artificial intelligence initiatives. Regarding operational performance, Microsoft delivered adjusted earnings of $4.27 per share against revenue of $82.9 billion for its fiscal third quarter — surpassing analyst projections of $4.05 per share on $81.4 billion revenue. Azure cloud expansion reached 40%. Microsoft’s infrastructure investments have escalated from $24 billion in fiscal 2021 to $88 billion in fiscal 2025, with projections indicating $190 billion for the current calendar year. These expenditures face intensifying examination as debates intensify regarding whether AI investments are translating into measurable customer returns. The corporation presently counts 20 million paying subscribers for its premium Copilot AI product, representing a fraction of approximately 450 million total enterprise seats. Tigress Financial Partners maintains a Buy recommendation with a $680 price objective — significantly exceeding current market levels — pointing to triple-digit annual growth in paid Copilot subscriptions. Nevertheless, the Wall Street Journal highlighted that certain clients have experienced confusion regarding Microsoft’s diverse AI product nomenclature, with some preferring Google’s Gemini alternative. Microsoft recently reorganized its AI division leadership. Judson Althoff, who assumed control of commercial operations in October, dismissed these worries: “They don’t concern me, because I think the market is still trying to figure out AI.” A research paper released by Microsoft Research this week introduced complexity to the AI optimism, determining that large language models “introduce sparse but severe errors that silently corrupt documents, compounding over long interaction.” The paper’s three researchers are affiliated with Microsoft Research.