# Kaitlin Free, Turfway Park Racing Analyst / Alanna Nolan, Woodbine Manager of Racing Content / Mark MacDonald, Harness Driver

Page: https://stenobird.com/podcast/ponies-24-7-the-radio-magazine-7078697/kaitlin-free-turfway-park-racing-analyst-alanna-nolan-woodbine-manager-of-racing-content-mark-macdonald-harness-driver
Text version: https://stenobird.com/podcast/ponies-24-7-the-radio-magazine-7078697/kaitlin-free-turfway-park-racing-analyst-alanna-nolan-woodbine-manager-of-racing-content-mark-macdonald-harness-driver.md
Podcast: [Ponies 24/7 The Radio Magazine](https://stenobird.com/podcast/ponies-24-7-the-radio-magazine-7078697)
Published: 2026-03-20T17:59:36+00:00
Episode link: https://share.transistor.fm/s/dcdaaca9
Audio file: https://media.transistor.fm/dcdaaca9/659646fe.mp3
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Duration seconds: 3760

## Resource

Today, Larry goes one-on-one with Turfway Park racing analyst Kaitlin Free, who returns to Ponies 24-7 to break down one of the most important Kentucky Derby prep races of the season, the Grade three Jeff Ruby Stakes. Now the richest race ever held at Turfway Park with a purse of seven hundred seventy-seven thousand dollars, the Jeff Ruby offers one hundred Kentucky Derby points to the winner and features a full field of contenders looking to secure their place in the starting gate on the first Saturday in May. Kaitlin analyzes the field, discusses how the Tapeta surface can impact race outcomes, and explains the history and growing importance of the Jeff Ruby Stakes on the Derby trail. She also previews other stakes races on the card, including the Bourbonette Oaks, and shares insight into her career path and how she became involved in Thoroughbred racing at Turfway Park. Also today, Woodbine’s Manager of Racing Content Alanna Nolan joins the show to discuss the continued success of the award-winning docuseries Free Rein, which recently returned for its third season. Alanna takes listeners behind the scenes of the series, including the powerful “Healing with Horses” segment, and explains how story ideas are developed and brought to life. She reflects on the original vision for Free Rein, how it has evolved over the past three seasons, and its role in connecting new and younger audiences to the sport of horse racing. Alanna also discusses her career path that led her to Woodbine Entertainment and looks ahead to future projects, including preparations already underway for this year’s King’s Plate. Then, two-time O’Brien Award winning harness driver Mark MacDonald returns to Ponies 24-7 to share his remarkable and emotional journey back toward the sulky following a serie…

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