Derek Robey on deciding to retire after 40 years of coaching & his career crossroads before coming to Sioux Falls episode artwork

EPISODE · Feb 25, 2026 · 1H 5M

Derek Robey on deciding to retire after 40 years of coaching & his career crossroads before coming to Sioux Falls

from Happy Hour with John Gaskins · host John Gaskins

How do you know when it is time?   That's the big question involving the "R" word for so many people, and 61-year-old Derek Robey decided now is the time to retire as a head coach in high school basketball after spending his entire 40-year career in that role — the last 21 at O'Gorman in Sioux Falls.   It is also the question on the Happy Hour host's mind when it comes to when is the right time to sit down with Robey for an hour to look back on a basketball life and career that has been at full speed in sports his whole life, starting with his childhood and non-descript high school career in the hoops cradle of Mitchell.   Do you talk to the six-time state champion after it is all over, or when he is still in the throws of all the practices, play designs, player development, personal relationship building, bus trips and buzzer beaters?   We just couldn't wait. We caught Robey between a crushing last-second loss at Huron on Tuesday — he didn't arrive home until midnight — and a Wednesday practice ahead of Thursday's regular season finale against his alma mater, which will coincide with Senior Night and potentially his final game in the Knights gymnasium.   His final O'Gorman team has proven good enough to take the best teams in the state to the buzzer, but vulnerable enough to potentially miss the state tournament. The Knights are 11-8 and may or may not host their SoDak 16 game that will be the "play-in" game for the state tourney.   What will he miss? What will he be glad to have behind him? What will he do now? Is he sure he wants to give this up? How has the game and the high schoolers who play it changed the last 10, 20 years?   What made a bench warmer for nine-time state champion Gary Munsen at MHS want to become a coach? What did he take from Munsen's repertoire into his own coaching?  After spending the first 17 years of his career at both high schools in Aberdeen, what brought Robey to take over at O'Gorman? It is quite a story of a man at a career crossroads whose wife had a moment of serendipity — a sign it was time to move to Sioux Falls.   All his decision led to was leading the Knights — who had never won a state title in boys hoops and finished runner-up the two years before Robey arrived — to back-to-back championships out of the chute, and five titles in his first seven years.   While O'G has hoisted the hardware only once since 2012, Robey has continued to gain respect as one of the best team builders and in-game chess players around, now and ever in South Dakota.   What's been behind it, besides, as the modest Robey said, "mostly luck?"   Pull up a bar stool at the Gateway Lounge and enjoy the answers.  

Episode metadata supplied by the publisher feed · Published Feb 25, 2026

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Derek Robey on deciding to retire after 40 years of coaching & his career crossroads before coming to Sioux Falls

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