After more than two decades at the ILT board and 18 years as chairman of the organisation, the former school teacher will sit in his last board meeting today.
The occasion created a mix of emotions for him, he said.
While he was pleased with everything he helped to achieve over those years, the 78-year-old confessed he was struggling a bit to say goodbye to such an important part of his life.
"I am a bit hesitant about the whole thing and asking people to not remind me about that," he said with a laugh.
"One thing that concerns me is that I certainly saw examples of people who turned off as they didn’t have a reason to get up after retirement — but I think this will not be me."
Mr Dennis decided to not stand again in this election as he believed the trust was in good hands and he had done his time.
He wanted to spend more time with his family and to enjoy passions which include horse racing and outdoor activities.
However, he hoped to keep an involvement with the trust from the sideline as an adviser.
"I joked that I will apply for a job at The Langlands hotel to be the doorman," he said.
But it was not always like that. More than 20 years ago, when he was principal of Tweedsmuir Intermediate School, he did not know much about the trust.
"The only thing I knew as a school principal is that they [ILT] gave a small school donation each year for school prizes."
Then through his role as chairman of Sport Southland, he was invited to be part of a group which would consider the possibility of building a stadium.
This had opened his eyes as he felt he was among people who had the means, the foresight and the power to get things done.
"I thought — hey, this is where decisions are made and I like that feeling."
With this in mind, he decided to stand for the ILT board and was successful in his bid.
But soon he found out the trust could not please everyone.
"One of the early lows happened when I joined the board. I was out taking some money from a cashflow machine in Waikiwi and a car pulled up and two blokes called out, ‘you are the f...... Mafia’.
"From that point in time, I’ve tried to make sure that the ILT is open and keep everyone well informed of everything we do."
Despite some criticism, he believed the model of the trust was sustainable because it had always "stuck to its knitting".
"It is the most effective, it is the most respected and most well-thought [trust] from people like the Internal Affairs who do the audits. So in another words — it works here.
"It was originally set up for the hospitality [sector] to return the profits for people in Invercargill. Full stop. And that is what we stuck to."
The ILT Stadium Southland and The Langlands were among the things he was most proud of and he treasured ILT’s contribution to the education sector.
During his time at the trust, the ILT was able to provide professional development in schools — sponsoring key staff to go overseas for training as well as promoting "huge" conferences in Invercargill for teachers.
He was also pleased ILT spent $5 million introducing interactive whiteboards into all Invercargill schools, and the establishment of the Enrich school for gifted children was a highlight.
"I love all the buildings and things we made, but in the end it is all about the people in our community."
His career had included 40 years in education, 12 years at the Invercargill City Council and 21 years at ILT, and he considered himself a fortunate man.
"I might not have much luck in the races [horse racing], but I know I am a lucky man in my life. That's good enough for me."
