[2] Henry ran for the position of Oshawa councillor Ward 5 in 2003 but was defeated by incumbent Cathy Clarke by 734 votes.

Henry said, "I'm not prepared to say people's vote doesn't matter...anything short of supporting this would be an insult to the residents of this city.

[9] Due to Henry's expense policy for his election campaign and his previous councillor work he was dubbed "Rob Ford East" by the Toronto Sun.

[13] In April 2015, the Supreme Court of Canada ruled that reciting the Lord's Prayer in a Quebec municipal council meeting violated that province's Charter of Rights.

While several cities outside of Quebec also decided to discontinue the practice, Henry said that it would continue in Oshawa, despite constitutional opinions that said the ruling likely also applied to the Canadian Charter of Rights and Freedoms.

"[14][15] On April 25, 2018, Oshawa residents Jeff Davis and former mayoral candidate Lou DeVuono delivered documents to the DRPS downtown station highlighting what they say is evidence of criminal wrongdoing at city hall, particularly in connection to a much maligned land purchase in 2013 for a new city works depot at 199 Wentworth Street East.