Kentucky Derby's brutal difficulty and iconic photo

Name: Kentucky Derby's brutal difficulty and iconic photo
Uploaded: 2026-05-04T13:03:09Z
Duration: 1 min 50 s
Description: Dave Portnoy explains why the Kentucky Derby is notoriously difficult to win and bet on, highlighting the racing luck and perfect trip needed for success. He praises an iconic photograph of two jockeys from the Ortiz brothers congratulating each other at the finish line, calling it one of the top 10 sports photos of all time, as the event continues to grow in popularity.

Wake Up Barstool · FS1 · May 4, 2026 · 1m 50s

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Dave Portnoy explains why the Kentucky Derby is notoriously difficult to win and bet on, highlighting the racing luck and perfect trip needed for success. He praises an iconic photograph of two jockeys from the Ortiz brothers congratulating each other at the finish line, calling it one of the top 10 sports photos of all time, as the event continues to grow in popularity.