The Cypress Group

The Cypress Group was founded in 1994 by four senior members of Lehman Brothers merchant banking group: Jim Stern, Jeff Hughes, Jamie Singleton, and David Spalding. The firm was established to focus on leveraged buyout transactions across various industrial sectors. At its peak in the late 1990s and early 2000s, Cypress was among the largest private equity firms in the United States, raising approximately $3.6 billion across two institutional funds in 1996 and 1999.

The firm historically employed an industry-based investment strategy, structuring its operations into six groups covering sectors such as automotive, aerospace, packaging, and financial services. Since its inception, the firm has invested more than $4 billion of equity in over 30 companies, with total transaction values exceeding $22 billion.

By the mid-2000s, the firm faced significant challenges due to a series of weak investments, particularly in its second fund. These difficulties led to the departure of several senior investment professionals and the abandonment of plans to raise a third fund in 2007. By 2009, the firm had entered a period of winding down its operations and managing the orderly exit of its remaining portfolio investments.