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Published on April 15, 2024

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Walgreens Boots Alliance (WBA) Short: 45.0% Alpha Based on CEO Ability

On June 9, 2021, ManagementTrack recommended a short position on Walgreens Boots Alliance (WBA), focusing on the newly appointed CEO, Rosalind Brewer. Our analysis, rooted in an exhaustive investigative process, raised concerns about Brewer’s fit for the role given her previous experience and the specific challenges facing WBA. This case study outlines how ManagementTrack’s unique approach to evaluating executive effectiveness informed our recommendation, leading to a successful outcome with a generated 45.0% alpha.

ManagementTrack’s Investigative Process

  1. In-depth Interviews: Conducted with former colleagues and peers of Rosalind Brewer, providing insights into her leadership style, strategic vision, and operational effectiveness.
  2. Experience Mapping: Analyzed Brewer’s career trajectory, focusing on her roles and achievements, to assess her suitability for leading WBA through its specific challenges.
  3. Strategic Fit Analysis: Evaluated the alignment between Brewer’s skills and experience with the strategic direction and operational needs of Walgreens Boots Alliance.

Why ManagementTrack Believed They Would Fail

  1. Lack of Industry Experience: Brewer’s previous roles did not provide her with the necessary background in pharmacy or healthcare, critical areas for WBA’s success.
  2. Strategic Misalignment: Concerns were raised about Brewer’s ability to drive the necessary strategic transformation at WBA, given her history of operational roles rather than strategic pivots.
  3. Leadership Style Concerns: Insights from Brewer’s former colleagues suggested potential challenges in her adapting to WBA’s culture and effectively leading the company through a period of significant change.

Outcome and Performance

The short position on WBA, initiated based on ManagementTrack’s analysis of CEO Rosalind Brewer’s fit and potential impact, resulted in a 45.0% alpha. This outcome validates ManagementTrack’s process and the importance of executive analysis in investment decision-making.

Key Takeaways

  1. Executive Fit is Crucial: The case underscores the importance of aligning a CEO’s experience and skills with the company’s strategic needs.
  2. In-depth Analysis Pays Off: ManagementTrack’s investigative approach, combining interviews with experience mapping, provides a robust basis for investment recommendations.
  3. Cultural Alignment Matters: Leadership style and the ability to navigate company culture are critical factors in a new CEO’s potential to succeed.


ManagementTrack’s recommendation to short WBA based on an in-depth analysis of CEO Rosalind Brewer’s suitability for the role exemplifies the value of executive-focused research. This case study highlights the importance of understanding the interplay between leadership capabilities and company challenges in predicting stock performance.

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