Watching Lillie Keenan’s poised execution in the tack, you’d be forgiven for not tagging her as a rider who struggles with confidence.

It’s hard to remember a time when the young American wasn’t winning. Her pony career alone is the stuff of legend, solidified at age 10, when she was champion in every regular pony hunter division at Pony Finals in Lexington, KY.

Her junior career was no less decorated. Keenan won Washington International Horse Show Equitation Finals at the age of 13 on a horse she’d only ridden for two weeks. She beat professional riders to win the USHJA International Hunter Derby Championship at 14 years old and took home three gold medals (two team, one individual) at the North American Youth Championships. Then there’s her equitation record that includes winning three of the Big Four titles, the USEF Medal Finals and the ASPCA Maclay Finals among them.

Keenan’s professional career started as promisingly. At 19, she was a member of the senior U.S. team that won bronze at the National Cup Final in Barcelona, Spain and took the individual bronze as well. With super horses in Super Sox and Fibonacci 17, Meredith Michaels Beerbaum Rio Games mount, she was a regular on the podium and the U.S. Team in 2016 and 2017.

And then things veered slightly off track, at least by Keenan standards. Between 2018 and 2020, Keenan won only two international classes, both in 2018 and none above 1.50m. (She podiumed in several).

Two years into the pro ranks, Keenan says her confidence was at an all time low. She reached out to Olympic medalist McLain Ward (USA) for help.

“I went to McLain when I was about 22, and to be honest, I had absolutely no self-confidence. I had a little bit of a rocky few years and I had experience at a high level, but I really didn’t believe in myself,” shared Keenan.

“Obviously, he’s a very talented teacher and he gives a lot of technical advice, but with me he basically just taught me to believe in myself again. He always jokes that I tell people he just told me to shorten my reins and have confidence. It sounds really simple, but that was a mountain for me to climb and it’s something that I still battle with every day and having him be the person to tell me that he actually believes in me meant more than anything.

“And he wasn’t just saying that.”

In four years, first under Ward’s tutelage and now under his mentorship, Keenan acquired the lessons and self-belief to take her riding to the heights anyone who’s been watching her career so far always imagined they’d reach. Just look at her Jumpr App stats.

In 2021, Keenan logged 23 podium finishes, including nine victories. Last year, she collected 20 more, including five wins and her first five star Grand Prix title.

This month, she’s cracked the world top 30 for the first time in her career, now sitting at world no. 28.

By next month, she’ll likely be top 25.

On Saturday at the Spruce Meadows National in Calgary, the 26-year-old won the biggest Grand Prix of her career to date with the CSI5* RBC Grand Prix of Canada, presented by Rolex. Aboard Fasther and as one of only two pairs to complete the 1.60m course on a single time fault, she topped a two-horse jump off against Canadian Olympian Mario Deslauriers. 

What a stunning Jumpr App #rideoftheday at the RBC Grand Prix of Canada, presented by ROLEX! Lillie Keenan (USA) aboard Fasther took first place!#SpruceMeadows #RBC #rolex #national #calgary #yyc #showjumpoing

Posted by Spruce Meadows on Saturday, June 17, 2023

It’s a milestone win in a month of career highs.

“I said to [Lillie] earlier, I think her and her horse win the most consistent pairing over the past month,” said Kara Chad (CAN), third place finisher in the RBC Grand Prix of Canada. “They’ve jumped three five star Grand Prix, been clear in them and I think been top four or five in each one. So pretty incredible.”

Keenan will be the first to credit her horse for the win, but their top results this past month have less to do with luck than with learning.

Keenan acquired Fasther as a nine-year-old and brought the Dutch Warmblood gelding to Spruce Meadows for Summer Series. He was her top horse at the time, but things didn’t go to plan.

I unfortunately had to rush him a bit to a high level, and I learned pretty quickly that I tried to go a little too fast up the ranks and he would not jump the bicycle jump last time I was here. So I purchased that fence and I got it at home. And it’s not an issue anymore,” said Keenan.

In 2021, Fasther was sidelined by an injury in the warm up at another iconic venue, Aachen in Germany. He spent the past two years rehabbing and returned to the show ring in 2023.

“I only jumped him at the end of the season in Wellington and really tried to aim him towards the summer to hopefully be able to use him for the American team,” shared Keenan. “We have some really important events coming up, so I’m just incredibly grateful to have him back. My team worked so hard through his rehab and every bit of it was worth it.”

Saturday’s win is proof.

“I don’t really have words,” said Keenan. “I’m really proud of my horse and just incredibly grateful.”

© Spruce Meadows Media/Mike Sturk
©Spruce Meadows Media/Dave Chidley