Prior to this leadership role, Aylward campaigned for the party’s leadership in December 2014 but was narrowly defeated by Rob Lantz on the second ballot during the leadership convention held on February 28, 2015.
On September 17, 2018, Aylward announced his resignation as the Leader of the Prince Edward Island Progressive Conservative Party. He stated that "It has become clear to me over the past couple of months that despite my best efforts, I have not been able to make a strong enough connection with Islanders."
Opposition House Leader (2015-2016): As the Opposition House Leader, Aylward was responsible for coordinating the opposition’s activities in the legislature, such as debating bills and review government policies.
Leader of the Official Opposition (2017-2018): In this role, Aylward led the main opposition party, challenging the government’s agenda and offering alternative policies.
Minister of Health & Wellness (2019-2021):
As the Minister of Health & Wellness, he administered the public health and healthcare systems and promoting wellness
Minister of Transportation & Infrastructure (2021-2023):
Aylward would was in charge of the development and maintenance of the region’s transportation systems and infrastructure projects.
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