It has been a long journey from Shepparton United, to a senior debut in 1982 for Melbourne, followed by 84 games and Life Membership in 1991.
Entering the coaching arena, from 1992 to 1996 Connolly coached Eastern Ranges, before serving as reserves and senior assistant coach at Hawthorn from 1996 to 2001.
It was at the start of his tenure with the Hawks that the experience of having been at Melbourne emerged in the strangest of ways - as Connolly himself says, ‘when I went and worked at Hawthorn in 1996 as an assistant coach, and I was also a Life Member of Melbourne, and both teams were going to merge … that was a very messy time.’
From Hawthorn, Connolly took on the senior role at Fremantle from 2002 to early 2007, including the Dockers’ inaugural finals series in 2003, and another turn at September action in 2006.
From the Victorian heartland of the game, he was headed to a new world.
‘Fremantle was $8 million in debt, and no-one came to watch them play, and they’d just won the wooden spoon. When I was appointed coach, I was appointed club coach, not just team coach, because we were going to have to do a lot of things to get the club up and about … my first pre-season, I took a week off and travelled all the way down west, having breakfast, lunch and dinner at different places, just trying to muster up some support.’
Fremantle, it had to be admitted early on, was a challenge for Connolly. ‘It was tabled that we had about 20 000 members, but we probably had about 15 000 - six years later, we’d done a lot of hard work to engage everyone, we were up around 36 000, we were selling out all our games, and we were starting to get financially active.’
Much of this was, of course, due to the on field gains that were being made. ‘My second year coaching, we made the finals, my third and fourth years we had eleven wins each year, and in my last year we made the Preliminary Final. It was an exciting time to take the club from being fragile on and off the field to being a pretty strong club.'
Many of the contributions to the increasing strength of the new club came from former Victorians, with a definite red and blue tinge dominating.
From Connolly as coach to Cameron Schwab as CEO, then complemented by the likes of Stephen Icke, Kelly O’Donnell and Earl Spalding in determining the on field set up of the fledgling Dockers, familiar names abounded.
But, as Connolly discovered, the locals were very proud of their game in its own right.
‘Western Australian football has a very deep culture, it’s underestimated over here in the east, and the people in the west are very proud of their WAFL connections.
There have been a lot of great players come through the WAFL, and per capita it’s more passionate than Melbourne in terms of the footy, because there’s nothing else on. The footy is the show in town.’
Realising this pride and commitment was important to Connolly, and has remained so throughout his thirty-plus years in the game. ‘There’s the business and the romance of the game. The business is pretty hard core, and I’ve certainly been involved in that all my life. I’m a Life Member of Melbourne, so I’ve always had an interest, but you don’t get caught up in the romance when you’re in the four walls, and that can have its strengths and its weaknesses.’
There can also be moments of humour, as Connolly recalled when harking back to Melbourne’s last finals appearance - the 2006 semi final at Subiaco, when he coached the Dockers to a 28 point win over the Demons.
Before this, however, Connolly had to deal with the attachments of the game. ‘My youngest son, Jade, is a very keen Melbourne supporter - the others would swing around depending on which club I’m working at. Here was I, coaching against Melbourne at Subiaco in the finals, and my son came out to jump in the car in a Melbourne kit, with a Melbourne jumper on. So, I had to send him back inside to get changed, considering that Fremantle was paying my salary!’ It was undoubtedly the start of quite a long day for young Jade.
Soon enough, however, the Melbourne colours were back in force for the Connolly clan, as they headed back east from Dockers to Demons.
‘I thought Melbourne was a challenge’, says Connolly. ‘I started at Hawthorn in 1996, when they were broke, and they got their act together. I left there at the end of 2001, and I was at Fremantle in 2002, when they were broke, and they ended up pretty powerful off the field. I learned a lot through those campaigns, and I was pretty confident that if we got our act together, we could at least get back in the game of getting the Club up and about.’
While the challenges were immense - and continue to be so - at least there are achievements as well, and Connolly has been a part of all of them.
‘We’ve got AAMI Park, there’s been list reshaping, the Bentleigh Club arrangement, the connection with Casey, improving revenue streams, re-establishing the links with the MCC - we’ve all done some special things. But it’s unrelenting, is footy. There are no free rides - it’s tough. And we’re going through a tough time now.’
One thing, though, that Connolly takes from footy through all the tough times - and that balance between the business, the romance, the camaraderie and the commercialism, is that he has connections, friendships and memories wherever he goes.
‘You can always pick up where you left off - that’s the great thing about footy.’