[6][7] His financial support for a 2008 California constitutional amendment to ban gay marriage resulted in some calls for a boycott of his hotels.

He then went to San Diego State College (now University), where he was a member of Sigma Chi and worked as a campus representative for an insurance company.

[21] In November 2013, he bought eight local weeklies in the San Diego region, which continue to be published as separate papers.

[22] In 2015, Manchester sold The San Diego Union-Tribune to Tribune Publishing Company[23] after selling the building for redevelopment.

He also had major holdings in Brookfield Asset Management, Disney, Apple, Exxon Mobil, Wal-Mart, Ford, tronc, and Pfizer.

[25] The Washington Post has noted that Manchester "has a hand in dozens of other businesses, including biotechnology, mortgage receivables, and television and movie productions.

Covering 3 million square feet and eight blocks of urban oceanfront, the project will include a 17-story Navy headquarters; three office towers, respectively 29, eight, and six stories high; a retail "paseo"; an 1100-room convention hotel; a 260-room luxury boutique hotel; a museum; a park; and a pedestrian walk along the entire length of the site.

[27] In 2018, The Washington Post reported that during his four years as the owner of the San Diego Union-Tribune, Manchester "employed an unconventional, anachronistic management style that upended the newspaper's culture and made many female workers uncomfortable."

"[33] His prominent support for the initiative, which was narrowly approved by voters in November 2008 but was ultimately ruled unconstitutional, led to calls by gay-rights groups for a boycott of Manchester's hotels.

[8] At his August 2017 Senate hearing about his nomination for an ambassadorship, he said that he now regrets supporting the initiative and believes that same-sex marriage should be legal.

[40] Two weeks after Trump's inauguration, Manchester said that "for the first time, a true capitalist is in the White House, an incredibly smart man with a big heart and an amazing family.

[44] The committee advanced his nomination to the full Senate on September 19, 2017,[45] but it failed to receive consideration before being returned to the President on January 3, 2018.

[52] He sponsors the Child Abuse Prevention Foundation in San Diego County and contributes money to the Preuss School, Monarch School, Polinsky Children's Center, Southern California Boys and Girls Club, Scripps Memorial Hospital, and San Diego Diocesan Ministries.

He has served on the board of trustees for the Sanford Burnham Prebys Medical Discovery Institute[55] and the San Diego Symphony.

[56] In January 1965 he married Elizabeth "Betsy" Manchester, whom he met when both were students at San Diego State; they have five children and thirteen grandchildren.

During their four decades together, according to The Washington Post, they "lived an opulent lifestyle that included multiple homes, one an $18 million mansion on the Pacific coast, as well as regular use of private jets and extensive travel.

[61] Manchester listed the family home, the Foxhill Estate purchased from David C. Copley in 2015, for sale in January 2020 according to The Wall Street Journal.