Paul Allen had an impact on Oregon, both as owner of the Portland Trail Blazers and as co-founder of the business giant, Microsoft Corporation. Allen was born in Seattle in 1953, and he met fellow Microsoft founder Bill Gates when Allen was in ninth grade and Gates was in seventh. Their partnership evolved through several stages: high school computer nerds, development of a Traf-O-Data system for counting automobile traffic, work in 1973 on a project to computerize management of Pacific Northwest dams, partners in the creation of a software startup company in Albuquerque, and return to the Seattle area in 1979 with the renamed Microsoft Corporation.

In its new home, Microsoft flourished when it crafted a partnership to develop the operating software for IBM's line of personal computers (MS-DOS or Microsoft Disk Operating System). Over the following two decades, the company achieved a commanding, if not always popular, position in the software industry through Windows and its associated applications programs (e.g., Word, Excel, and PowerPoint). As a result, Allen and Gates became two of the wealthiest individuals in the world.

Allen retired from active participation in Microsoft in 1983 after being diagnosed with Hodgkin's disease and left the Microsoft board of directors in 2000. He has since lived an often lavish lifestyle while exploring business opportunities in the entertainment industry (e.g., investing in DreamWorks SKG), in technology companies, and in central Seattle real estate, with a particular interest in the South Lake Union area. He has funded such special interests as the Experience Music Project and the Science Fiction Museum and Hall of Fame, both in Seattle.

Allen also set up the Paul G. Allen Family Foundation, which gives millions of dollars to nonprofit organizations in the Pacific Northwest—12 percent directed to Portland. The multi-million-dollar Paul Allen Pavilion was added to the outdoor Elizabethan stage of the Oregon Shakespeare Festival in Ashland in 1992, and in 2008 the foundation donated an additional $300,000 for productions in the 2008–2010 seasons.

Allen bought into professional sports as well. He purchased the Seattle Seahawks in 1997 and the Portland Trail Blazers in 1988. He was also part-owner of the Seattle Sounders Football Club. In 1993, he built Portland's Rose Garden Arena, with considerable investment from the City of Portland.

Allen was a controversial figure in Portland because of his alleged micromanagement of the Blazers and his financial manipulations of the Rose Garden Arena. His subordinate company, which managed the arena, the Oregon Arena Corporation, declared bankruptcy in 2004, and he repurchased the arena from creditors in 2007. Changes in team management and personnel choices in 2007 improved his reputation among Oregon basketball fans. Allen died in 2018 from non-Hodgkin's lymphoma.