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Diary of a (football) CEO: 'Hiring Askou was a calculated risk, selling Miller was excruciating'

Brian Caldwell, Motherwell. Part Two

Dec 28, 2025
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Welcome to part II of award-winning sportswriter Stephen McGowan’s observation of the life of a football club chief executive officer — Brian Caldwell of Motherwell. Yesterday, Brian told us about the particular challenges associated with a fan-owned club.

In Part II today, Brian lifts the lid on the hiring of Jens Berthel Askou and the smart recruitment which turned the team into one of the stories of the Scottish season.

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By Stephen McGowan

Over three decades as one of the old stagers of British football, Brian Caldwell has worked with 17 different managers. Three of them have come during a dramatic 12 months when turmoil at Motherwell turned to triumph.

In January Stuart Kettlewell left after two years, citing the effect of abuse from fans. Replacement Michael Wimmer lasted a mere 12 games before family issues drew him back to Germany to join third-tier club Jahn Regensburg.

When a type of manager fails, football clubs have an impetuous urge to rip up the model they favoured before and go in a different direction. When the time came to ponder Wimmer’s replacement, a three-man selection subcommittee consisting of Caldwell, chairman Kyrk MacMillan and Well Society board member Greg Anderson held their nerve. Despite cutting his time short for personal reasons, Wimmer had won five and drawn three of his 12 matches.

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