CELEBRATING THE AUCKLAND CUP | We chat to Auckland Cup pros, the O'Leary's

7 Mar 2023
Auckland Thoroughbred Racing

The O’Leary brothers are perhaps best known in racing circles for being the owners of the crowd favourite galloper with the GREAT name, Who Shot Thebarman.

Who Shot Thebarman headed to Australia, fresh off of winning the Group 1 Auckland Cup here at Ellerslie in 2014. In Australia alone he started in six Sydney Cups, four Melbourne Cups, four BMWs, three Moonee Valley Cups, three Zipping Classics and two Caulfield Cups, winning over $A4.5 million for the O’Leary clan.

But that’s not the only association the O’Leary’s have had with the Auckland Cup…

In 2018, Humphrey and Fiona O’Leary had another trip into the winner’s circle when Ladies First won the Barfoot & Thompson Auckland Cup by the smallest of margins. A gutsy performance it most certainly was and her $300,000 payday dwarfed her $8,000 purchase price from the 2014 NZB National Weanling, Broodmare and Mixed Bloodstock sale.

With 2023’s event just under 2 weeks away, we turn our attention to a similarly named gelding in Ladies Man, also trained by Allan Sharrock. The half-brother to the aforementioned Ladies First, Ladies Man is preparing to following in his sister’s footsteps and take to the track in the 2023 Barfoot & Thompson Auckland Cup, being run at Pukekohe Park this season due to Ellerslie’s track upgrade.

And as luck would have it, the O’Leary’s feature in Ladies Man’s ownership group as well…could 2023 provide them with another win in the historic Auckland Cup? Only time will tell…!

We chatted to Humphrey and Fiona O’Leary earlier this week to find out what it’s like to have had such wonderful horses…

You’ve had a very successful association with the Auckland Cup to date, can you tell us what it’s like to win one of New Zealand’s most iconic races not once, but twice?

Humphrey: Well, it is a dream come true really. Over the years we’ve watched a lot of Auckland Cups and when you finally have a horse start in it like Who Shot Thebarman who went into the race hot favourite and then won so well, it makes for an amazing day. I had a share in him with my brothers and even our mother came up that day to watch him. That was the first time she had been to the races for a many a year, all the sisters and brothers and everybody was there and the horse delivered and it was a very special day. You plan things and you dream things and dreams do come true.

Matthew Cameron riding Who Shot Thebarman celebrates after winning the Auckland Cup. Credit: Stuff, Chris Skelton


And then to win it again with Ladies First in 2018…

Humphrey: That was another dream. We’d won the Wanganui Cup and she won that so well we hatched a plan to target the Auckland Cup with trainer, Allan Sharrock. She had spelled well after the Wanganui win so we headed up and everything was going to plan and we had Vinny Colgan on to ride her but then he got suspended! After that we were jockey searching and we ended up with Jonathan Parkes. He got hampered pretty much the whole journey by the northern riders and they wouldn’t let him get a clear run, so he worked overtime. She won the race but it was a very close finish and had some heart stopping moments!

Ladies First returning to the Birdcage


Who Shot Thebarman gained quite the following over the course of his racing career. What do you think it was about him that captured the hearts and attention of the racing public?

Humphrey: Probably his ability in all his staying races. I think most people really love a good, honest stayer and most of his races were pretty genuine and you look at his race record, to start in 4 Melbourne Cups plus all those other big races, it was amazing to think he could still do all that and keep going.

When he retired his legs were still strong and he was still so sound. Most people respected him in the stable because in his work and that he was just a tough horse.


If we think back to 2018 again when Ladies First took out the Cup, were you at Ellerslie that day?

Humphrey: Oh yes. Fi and I were there. We had a good bunch of loyal friends and watched the race from just past the post. From our angle we had thought she had only taken out second or third. When George Simon came out with the fact that Ladies First may have won, all of a sudden we thought, hang on, it was almost a shock! When she did win, wow what excitement. Peter Thompson was the sponsor for the second time [after Who Shot Thebarman’s win in 2014) and when I went up and did the speech I said to him “it was good to be back”. We had a great little party at the Ellerslie Ibis there and all enjoyed ourselves. It was a dream come true.

You said there was that awkward angle and Johnathan had to work extra hard. What went through your mind as the race progressed? Did you think she had a chance?

Humphrey: No, I really was thinking we can’t win. From what I’d seen early in the run, I didn’t think she’d be able to keep that run going to win the race. It was certainly a very pleasant surprise when her little lip or nose got through to beat Five to Midnight. It was amazing.

The 2018 running of the Barfoot & Thompson Auckland Cup was very tightly contested.


As an owner you’ve obviously had some success – is that what keeps you coming back and purchasing these horses and staying involved in the industry or is it just a love for thoroughbreds and racing?

Humphrey: It’s the latter really. Fiona and I just love racing and the sport of it. You look at a horse in the paddock and you don’t know till you put the silks on how fast or slow they are but you give every horse every opportunity. We were at the trials yesterday down at Foxton and our horse won the trial and Andrew Lacy came and had a chat and said ‘I always wanted to ask you both – you two have been to a lot of big races but you still come to these Foxton trials’, we just said as far as we’re concerned if you’ve got a horse, especially one that we own 100%, you just go and give her a pat and see her perform no matter where they are running. You make plans where she could start next and that’s all part of it for us, it’s the whole journey, the weight she’s carrying, how she’s looking. And then sometimes you can see your horses and know that’s the end of their campaign and you think that will do, they can come home. We’ve got lovely paddocks for them so it’s easy and we love having them.

Auckland Cup winner, Ladies First. L-R: Sheila Laxon, first female trainer to win a Melbourne Cup, owner Fiona O’Leary, jockey Lisa Allpress, Emma Davies from Sharrock Stables, Allan Sharrock, Ladies First’s trainer and owner Humphrey O’Leary, with the Melbourne Cup.


What would you say to others that want to get involved? Ladies First only cost $8,000 at the NZB Weanling Sale, so she wasn’t an expensive buy and I can imagine you’ve had a lot of joy from that association alone. Would you encourage others to get involved?

Humphrey: Oh look it’s a great game. Fiona’s really only been involved in the last 10 years and she’d probably be able to answer that question better than myself. I’ve been in it a lifetime but she’s looking at it with a new perspective.

Fiona: Oh definitely. We have a lot of friends that have come along with us to the races that weren’t involved in racing, like my netball team. They’ve all come along and had a great time! It’s easy when you’re farmers and you’ve got the land but other than that there are so many starting points. You’ve got the syndicates all around and you get the thrill of seeing your horse win and experience that ownership feeling. To us it’s not the money that you win, we love it no matter whether we’re watching one at Wanganui or watching one at Ellerslie! You get the same buzz and jump around with a win.

You are now a part owner of Ladies Man, half brother to Ladies First, who now also has a chance in the Barfoot & Thompson Auckland Cup. Do you aim for that race or is it just a happy coincidence?

It’s a bit of both really. We got into the horse because of Ladies First, and with Ladies First’s breeding and then with the Zed in him, they are such a good staying bloodlines. It did seem like a natural progression to aim for the same races.

Ladies Man is on target for Saturday’s Gr.2 Auckland Cup (3200m). Photo: Grant Matthew (Race Images)


And will you be joining us on Barfoot & Thompson Auckland Cup Day at Pukekohe Park?

Yes, definitely! We’ll be flying up for that!

We look forward to welcoming Humphrey and Fiona to Pukekohe Park to cheer on Ladies Man and wish them all the best. Let’s see if Humphrey can once again encounter Peter Thompson in the winner’s circle!

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