The 35-year-old opener is in his 11th season with Otago after five summers with Canterbury.
He has played an awful lot of cricket to have never been part of a team which has won the first-class title.
Otago has had an even longer wait - 26 long years, to be exact.
The Volts finished second last year, and second the year before that. Being the bridesmaid gets tiring fast.
''That is our challenge and I know the guys are keen to win the Plunket Shield,'' Redmond said.
''I'm in my 11th season here and I don't know how many I had at Canterbury but I've never won it.
''I reckon it is the hardest comp to win. In four-day cricket you can't play the first two days well and hope to win a game. You've got to play all four days to get a result.''
The burden of squeezing more consistency from the Volts will, in a large part, fall on Redmond's shoulders. He has replaced Derek de Boorder as captain this season.
It is not Redmond's first stint in the role. He took over from Craig Cumming in 2011-12 and it did not go well.
From a captaincy point of view, Redmond was well-equipped, but he was just batting so poorly his place in the team became untenable.
He was eventually dropped from the side in all three formats and de Boorder took over.
So, when rookie Volts coach Dimitri Mascarenhas phoned Redmond to sound him out about the captaincy, the right-hander needed a few weeks to mull it over.
He rang his father, Rodney, for some advice. That is the same Rodney Redmond who scored a hundred on test debut and never played test cricket again.
''I rang him up in Perth and talked to him for quite a while and just reached the decision, 'well, why not? Just get in there and get stuck in again'.
''The last time, I didn't have the best run at it because of my form. But I look at myself. I'm 35 now, and I wouldn't mind actually trying to give something back to Otago and to the young guys coming through. It would be nice to aid in their development and give something back to them.''
Redmond was not convinced his promotion to captain was a major factor in his form slump three years ago. He felt it had more to do with an inability to get on top of the mental side of the game.
In 2011-12, he scored 157 runs at 14.27. For someone with a career average north of 35, and 15 first-class hundreds, it was a dramatic slide.
But the following summer Redmond was the leading scorer in the Plunket Shield with 941 runs at an average of 55.35.
It is hard to imagine two more contrasting seasons.
''I think I manage myself better now. I think my mental game is a lot better and that is something I didn't really concentrate on in the early days.
''A big thing about being a professional sportsmen is being able to juggle your responsibilities. I've found in the last couple of years the form has been there and I've got the mental side of the game down pat.
''Maybe it was just one of those off seasons. The best thing about it was I came back a better player the following year and have kicked on.''
Last summer Redmond was recalled to the Black Caps as a replacement for the injured Kane Williamson for the first test against the West Indies in Dunedin.
Williamson was fit for the second test and Redmond returned to domestic cricket, but the veteran is clearly still in the selectors' minds.
Tom Latham has one opening berth secure for now but Hamish Rutherford's grip on the other is more tenuous.
Redmond has not given up on adding to his eight test appearances.
More immediately, though, he is focused on getting Otago off to a positive start in the Plunket Shield.
The Volts' opening game is against Central Districts in Napier, beginning on October 26.
A couple of new faces will be in line for an Otago debut. Tipene Friday (Wellington) and Roald Badenhorst (Central Districts) have transferred south.
The not-so-secret secret to doing well at first-class level is to have a good stable of bowlers.
It is a long season and the good sides can still field quality attacks even when injury strikes.
Otago has lost the services of former Black Cap Ian Butler to retirement.
Batsman Neil Broom has transferred north to Canterbury and is another big loss.
The national team has a jam-packed calendar this summer and that will rob the Volts of the services of Brendon McCullum, Nathan McCullum and Jimmy Neesham for large chunks of the summer, while Mark Craig, Neil Wagner and Hamish Rutherford will also be absent while on duty for the test team.
Otago's depth will certainly be tested.
