Cockrill was raised in Chilliwack, British Columbia and graduated from Trinity Western University (TWU) with a Bachelor of Business Administration in 2012.
[1] Cockrill won the Saskatchewan Party nomination for The Battlefords ahead of the 2020 provincial election after two-term incumbent Herb Cox announced his retirement.
A sworn affidavit in court showed that the Ministry of Education had received 18 letters expressing concern about pronouns in school between June and the introduction of the policy in August.
[16] The Parents' Bill of Rights, which amended the province's Education Act, also contained a provision making it a legal requirement for schools to fly the Saskatchewan provincial flag.
[20][21] After teachers rejected two separate government contract offers in May 2024, the two sides agreed to send the dispute to binding arbitration, slated to take place before the end of 2024.
[25] The second investigation, announced in September, targeted Cockrill's personal investments in two helium companies partnering with and receiving tax breaks from the provincial government.