Crosbie is the eldest of three children of Jane and John C. Crosbie. His father was a prominent figure in Newfoundland and Labrador and Canadian politics, a provincial and federal cabinet minister who also served as Lieutenant-Governor of the province. Crosbie is also a grandson and namesake of Chesley A. Crosbie and the great-grandson of Sir John Crosbie, prominent businessmen and public figures in Newfoundland. Crosbie's early education was at Bishop Feild College in St. John's, and at St. Andrews College in Aurora, Ontario. He was selected as Newfoundland and Labrador's Rhodes Scholar in 1976, studying jurisprudence at Oxford, and continued his legal studies at Dalhousie University. There he met his future wife, Lois Hoegg, a native of Stellarton, Nova Scotia. She has been a Justice of the Newfoundland and Labrador Supreme Court since 2007. They have three daughters.
Lawyer
On completing law school, Crosbie returned to St. John's and was admitted to the bar in 1983. He founded Ches Crosbie Barristers in 1991. The firm developed expertise in class actions, and Crosbie first came into the public eye as an advocate for breast cancer patients affected by delayed and erroneous test results, for the victims of moose-vehicle accidents, for users of video lottery terminals, and for the former residents of residential schools in Labrador. Crosbie was appointed Queen's Counsel in 2004. From an interest in helping injured children, Crosbie and his firm have given away thousands of bicycle helmets to young people across the province. He has worked on a pro bono basis with former shipyard employees attempting to get compensation for long-term health problems. He has also volunteered with heritage organizations such as the Sealer's Memorial and Interpretation Centre in Elliston, Trinity Bay, and worked with the Placentia Historical Society and Town of Placentia to commemorate the 75th anniversary of the 1941 meeting of U.S. President Franklin D. Roosevelt and British Prime Minister Winston Churchill which established the Atlantic Charter.
Politics
Crosbie's earliest involvement in politics came as a supporter of his father, who was a candidate for the leadership of the Progressive Conservative Party of Canada in 1983. He is a long-time provincial Progressive Conservative and federal Conservative supporter. In 2014 Crosbie announced his candidacy for the federal constituency of Avalon. However, in 2015 his candidacy was rejected by the Conservative Party of Canada, reputedly as the result of his "playful barbs" concerning Prime Minister Stephen Harper in a Shakespearean-parody fundraising skit. His father, John Crosbie then accused the federal Conservatives of squashing his son's candidacy because he was too independent and because Newfoundland senator David Wells wanted to keep his control over Newfoundland patronage appointments, an accusation that Wells denied.
In February 2017, Crosbie announced an exploratory candidacy for the leadership of the Progressive Conservative Party of Newfoundland and Labrador, following the resignation of leader and former PremierPaul Davis. On April 28, 2018 Crosbie defeated Health Authority CEO Tony Wakeham to succeed Davis. The leadership convention operated under a mixed vote-points system in which a hundred points were awarded in each of 40 districts across the provinces, based on the percentage of vote each candidate won. The final tally was Crosbie with 2,298.92 and Wakeham with 1,701.08 points respectively. In August 2018, Crosbie announced his candidacy for the district of Windsor Lake following the resignation of MHA Cathy Bennett. On September 20, 2018 Crosbie won the race and therefore became Leader of the Opposition. Crosbie led the party into the 2019 provincial election with the party increasing its seat count from 7 to 15. The PCs finished 1% behind the Liberals in the popular vote and the Ball government was reduced to a minority. Crosbie was personally re-elected in Windsor Lake. Crosbie endorsed Peter Mackay in the 2020 Conservative Party of Canada leadership election.
