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Since 2010, the 75 year old billionaire has applied this philosophy to football, achieving remarkable success at Liverpool - another iconic ball club that was teetering on the brink of an uncertain future before Henry's Fenway Sports Group swooped in to save them from bankruptcy.
Liverpool has reclaimed its spot at the apex of football over the past seven seasons and is on the cusp of securing a second Premier League title, matching Manchester United's record of being English champions for the 21st time.
Mohamed Salah, Virgil van Dijk and Trent Alexander-Arnold could all depart for free in the summer.
The fact that Liverpool have allowed this perfect storm to brew is not a good look for a club that prides itself on getting these things right.
However, Salah will be turning 33 in June, just a month before Van Dijk rings in his 34th birthday.
A decade ago, Liverpool let slip Raheem Sterling's £100,000-a-week wage demands, but it didn't stop the England winger from fulfilling his desire to join Manchester City.
This did result in Sterling becoming a target of animosity for the Kop.
Mohamed Salah and Virgil van Dijk are set to see their contracts expire.
Salah and Van Dijk appear to have plenty of fuel left in their tanks
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