[6] Chester was viewed as a potential candidate to replace Barnaby Joyce as National Party leader in February 2018; however he chose not to contest the leadership.

Prior to entering federal politics, he worked as a newspaper and television journalist throughout Gippsland and was chief of staff to Peter Ryan, the leader of the Nationals in the Victorian state parliament.

[citation needed] Chester contested Gippsland East as the National Party candidate at the 2002 Victorian state election, losing to independent Craig Ingram.

[12][13] Public scrutiny of taxpayer-funded travel allowances usage by MPs has embroiled Chester in controversy.

It would later emerge in May 2020 during the recriminations over McCormack's refusal to support a planned run for federal parliament by NSW Deputy Premier John Barilaro in the 2020 Eden-Monaro by-election that Chester was in a WhatsApp group where messages about Barilaro and his wife were exchanged with colleagues Damian Drum and Kevin Hogan.

[16] For supporting incumbent McCormack in the 2021 Nationals leadership spill, Chester was stripped of his ministerial portfolios by new leader Joyce.

Chester has been a frequent critic of Barnaby Joyce, labelling him ‘incoherent’, criticising his leadership style and scepticism of climate science.