Going Private and Insider Sell-Offs: Navigating Strategic Risks in Walgreens and Salesforce

The corporate landscape is rife with contrasting narratives: one of certainty and consolidation, the other of doubt and divergence. Walgreens Boots Alliance (WBA) is nearing the completion of its long-awaited going-private transaction, while Salesforce (CRM) faces skepticism as insiders sell shares amid strategic overhauls. Both scenarios highlight the tension between strategic opportunities and operational risks, offering investors distinct paths to navigate.

Walgreens: Cash Certainty vs. DAP Rights Uncertainty

Walgreens shareholders overwhelmingly approved its $10 billion going-private deal led by Sycamore Partners on July 11, 2025. The transaction offers investors $11.45 per share in cash upfront, plus a Divested Asset Proceeds Right (DAP Right) tied to the eventual monetization of VillageMD—a division sold to Blackstone for $5.1 billion in 2023. The DAP Right entitles shareholders to an additional $3.00 per share, but only if VillageMD's assets (including its equity stake in Summit Health and CityMD) are successfully sold or liquidated.

Opportunities for Arbitrageurs:
The cash component offers immediate liquidity, appealing to investors seeking to exit a struggling retail pharmacy business. Walgreens' plan to close 1,000 U.S. stores by 2027 underscores its need for operational restructuring, which may proceed more swiftly under private ownership.

Risks for Long-Term Holders:
The DAP Right is a double-edged sword. While the potential $3.00 upside is enticing, its value hinges on Blackstone's ability to extract profits from VillageMD—a division that contributed to Walgreens' $8 billion net loss in 2024. Regulatory delays or a weak healthcare market could render the DAP Right worthless.

Salesforce: Insider Sell-Offs and Valuation Concerns

Salesforce's recent insider activity raises red flags. CEO Marc Benioff sold $598,854 worth of shares in July 2025, reducing his ownership by 0.02%. Over the past year, insiders sold $9.5 million of shares versus $1.5 million in purchases. Notably, Srinivas Tallapragada, Salesforce's president, offloaded $2.5 million of shares at $253—a price below the stock's then-current value of $274.

The stock has declined 17% year-to-date, trading near its 52-week low. Analysts warn of valuation risks: Salesforce's P/E ratio of 40.58 and dividend cut (to $0.416 per share) suggest a focus on reinvestment over shareholder returns. Meanwhile, the proposed $8 billion acquisition of Informatica—a move to bolster its Data Cloud platform—faces execution hurdles.

Strategic Crossroads:
Salesforce's AI-driven tools, like Agentforce (with $100 million in annual recurring revenue), are promising, but competition from Microsoft's Copilot and Oracle's generative AI tools looms large. The insider selling reflects skepticism about whether Salesforce can sustain growth in a market where rivals are aggressively integrating AI into enterprise software.

Contrasting Investment Strategies: Selectivity Over Caution

Walgreens DAP Rights: A Speculative Gamble

• For Arbitrageurs: The cash component offers a “bird in hand” return, while the DAP Right is a “maybe” bonus. Investors bullish on Blackstone's healthcare investments or VillageMD's future could overweight the DAP.
• For Long-Term Holders: Avoid the DAP unless you're willing to bet on Blackstone's ability to unlock value in a volatile healthcare sector.

Salesforce: Proceed with Caution

• Avoid Overpaying: The stock's P/E ratio remains elevated relative to its growth trajectory. Insider selling and mixed analyst ratings (2 “Sell,” 8 “Hold”) suggest the market is pricing in execution risks.
• Wait for Catalysts: Hold off until Salesforce delivers clearer signs of AI adoption (e.g., Agentforce's scalability) or resolves leadership uncertainty (e.g., its CFO transition).

Broader Market Implications

The Walgreens-Salesforce dichotomy underscores a growing theme: private equity's role in restructuring underperformers versus tech giants' reliance on innovation to justify valuations. Investors must ask: Is the certainty of cash (as in Walgreens) worth the cost of missing future upside, or is the potential for tech leadership (as in Salesforce) worth the risk of overvaluation?

Final Take: Prioritize Clarity Over Ambiguity

• Act on Walgreens' DAP Rights only if you're speculative and bullish on Blackstone's healthcare bets.
• Avoid Salesforce until valuation metrics align with growth prospects or insider sentiment reverses.
• Watch for regulatory approvals and operational updates in both cases—these will determine whether strategic risks or opportunities ultimately prevail.

In a market seeking stability, Walgreens offers a defined exit, while Salesforce's future hinges on execution. Choose your path wisely.