Under scrutiny for his role in the HRM concert scandal and as executor for the will of Mary Thibeault, Kelly left politics in 2012 citing 'personal reasons'.
Kelly holds a Diploma in Hospitality Management from the Nova Scotia Community College and a Master of Business Administration (MBA) from Saint Mary's University.
During Kelly's time as mayor, the region installed a large and long-delayed sewage treatment system known as Halifax Harbour Solutions which came into operation in 2008, broke down and was restored in 2010.
Kelly was criticized for the failure of the city's Harbour Solutions sewage treatment plant which had faced delays and breakdowns.
[7] He was instrumental in allowing a controversial $400,000 loan of public money for a Black Eyed Peas concert in 2010 which was not approved by HRM council or reviewed by the city's legal department.
Occupy protesters agreed to temporarily move out of Halifax's Grand Parade for the Remembrance Day ceremony and shifted their camp to Victoria Park.
[20] In June 2012 five of 18 beneficiaries had petitioned the province's probate court to have Kelly removed as executor[21] alleging he had taken nearly $150,000 from the estate[22] and that the will was still not settled seven years after Thibeault's death.
[23] In September 2012 the issue was resolved when Kelly agreed to step down after probate judge ordered him removed as Thibeault's executor.
On July 7, 2016, Westlock County chief financial officer Sue Oberg told council that Kelly had approved $390,570 in un-budgeted expenses while CAO.
[32] When completed in July 2017 the report[33] concluded Kelly breached the Alberta Municipal Government Act on a number of occasions.
In particular it stated "In apparent enthusiasm for economic development, Kelly acted without proper authority and failed to advise council of their legislative responsibilities.
The inspectors stated that it appeared the Baptiste Lake Fire Hall drawing were being used as a cost saving measure to avoid hiring an engineer or architect.
[31] Kelly stated that documents were destroyed after he departed Westlock and as a result the investigators relied on interviews and allegations rather than facts.
"[38] Initially, Kelly was hired with a six-month probationary period, which was extended an additional six months when news of the Westlock investigation surfaced.
"[41] In October 2017 it was reported that Kelly was at the centre of increased labour unrest with city hall workers, who were exploring joining a larger union to better represent themselves.
[43] On January 23, 2019, it was announced that Deputy CAO Scott Messervey no longer worked with the City of Charlottetown, and at the time no reason for the departure was given.
[1] In September 2021, Kelly and Diana Girouard bought an oceanfront property on Eagle Head Road in Queens County, Nova Scotia.
[49] In October 2022, more than two dozen area residents filed a lawsuit against Kelly and Girouard in the Nova Scotia Supreme Court, alleging that they had blocked a "well-marked and commonly recognized right of way" on their property.