Bored in the office staying way past I need to and was wondering about some of the biggest dick plays done in PE history. Sycamore’s takeover of Walgreens being larger than firm AUM is what got me thinking.
They don’t have to be super large $ wise, but there’s got to be some crazy “all-in” bets that have been made over the years.
| +106 | Is Everyone Too Bearish on PE? | 34 | 23h |
| +48 | Why would anyone do PE in long term in 2026? | 13 | 1d |
| +35 | MF Tech PE 2026 | 7 | 20m |
| +24 | Q&A: What It’s Actually Like Working at an Independent (Fundless) Sponsor | 4 | 3d |
| +22 | Do you think PE has actually helped you become a better entrepreneur? | 8 | 15h |
| +21 | Striking out in last rounds | 2 | 4d |
| +21 | UMM PE or High Paying Strat Finance? | 13 | 1d |
| +16 | Portfolio Marks | 8 | 12h |
| +15 | DELETE | 1 | 2d |
| +15 | Overwhelmed by amount of data / granularity | 3 | 2d |
Career Resources
Get instant access to lessons taught by experienced private equity pros and bulge bracket investment bankers including financial statement modeling, DCF, M&A, LBO, Comps and Excel Modeling.
Based on the most helpful WSO content, one notable "big dick play" in private equity history is Sycamore Partners' acquisition of Staples for $6.9 billion. This deal stands out for several reasons:
Sector Challenges: The retail sector was under significant pressure, with many chains filing for bankruptcy (e.g., Gymboree, Sears Canada). Despite this, Sycamore made a bold move into a struggling industry.
Strategic Focus: Staples' business model was shifting, with about 65% of its revenue driven by B2B sales, which Sycamore likely saw as a stable and lucrative opportunity. Additionally, only a minority of Staples' products were sold in brick-and-mortar stores, with $10.6 billion in sales being delivered to customers versus $6.6 billion in-store sales.
Leveraged Buyout Scale: The deal was the largest leveraged buyout of the year, with Sycamore paying $10.25 per share in cash, representing a 20% premium from pre-sale rumors. The financing involved major banks like UBS, BofA Merrill Lynch, Deutsche Bank, and others.
Operational Challenges: Staples had been experiencing declining sales and gross profits for four consecutive years, alongside a steady reduction in the number of stores. Sycamore's bet was not just financial but operational, requiring significant cost-cutting and strategic realignment.
This acquisition exemplifies a high-stakes, "all-in" private equity move, showcasing Sycamore's confidence in their ability to turn around a struggling but strategically valuable business.
Sources: Sycamore Acquires Staples for $6.9 Billion in Largest Buyout of the Year, https://www.wallstreetoasis.com/forum/investing/please-swipe-right?customgpt=1
Dolorem sunt temporibus sunt voluptates voluptate excepturi. Facilis ipsa quisquam et ab accusantium. Omnis labore aut porro aut tempora est ipsa vero. Ex nobis non voluptatum dolor fugiat. Eum autem consequatur odit et non adipisci ut nostrum.
Ea eos tempore pariatur. Necessitatibus ratione at qui quia. Dolor necessitatibus earum voluptatem in laudantium iste.
Unde voluptate dolores et enim autem et. Ut rerum veniam quis accusantium repellendus. Temporibus deserunt sint aut ad ea. Non temporibus dicta voluptatibus sed. Officiis officiis architecto rerum et fugit id.
Eos nisi repudiandae qui architecto sed. Necessitatibus facere dolor corrupti quo. Iure dolore voluptatem vitae et exercitationem debitis.
See All Comments - 100% Free
WSO depends on everyone being able to pitch in when they know something. Unlock with your email and get bonus: 6 financial modeling lessons free ($199 value)
or Unlock with your social account...