Todd Boehly may have finally got his man in Mauricio Pochettino but he's also been left to reflect on another of his failed signings.
However, this time around it's not another underwhelming big-money player, but President of Business Tom Glick who is now heading for the exit door at Stamford Bridge - with one of Boehly's trusted allies replacing him. Glick came on board in July amid a glowing reputation, having previously served as Chief Commercial Officer of the City Football Group and a CEO at Derby.
And upon his initial appointment, the American businessman was glowing in his praise, saying: "Tom's successful track record as a leader and innovator at several respected and winning sport organisations made him the obvious choice for this position."
But amid a chaotic season in West London, the club released a statement on Tuesday: "Tom Glick, president of business, has decided to step down from his role to pursue other opportunities," it read. "He will be working closely with Jurasek in the coming months on the transition before departing the club."
And Chris Jurasek will come the other way through the revolving door as Glick's replacement. He has previously worked with Boehly as an operating executive for Clearlake Capital, the private equity firm which co-owns Chelsea.
And the club confirmed: "Jurasek will take responsibility for all the business areas of the club and will report to the board alongside co-sporting directors Laurence Stewart and Paul Winstanley, who will remain responsible for all the sporting activities of the club."
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And in his own statement, Jurasek said: 'I’m delighted to be joining Chelsea, a club which is loved and followed all over the world. I’m enormously proud to be leading it into the next chapter in its rich history. We have huge opportunities to grow on and off the pitch and to engage our exceptional fans both in London and wherever they are supporting us from. I’m looking forward to working closely with our owners, leadership and everyone around the club."
Boehly will hope his new man can bring stability to the club after splashing out more than £585.5 million since competing his purchase of the club last year. But it's resulted in turmoil as opposed to triumph, with both Thomas Tuchel and Graham Potter sacked amid a 12th placed finish.
It was the club's lowest top flight placing since they were 14th under Glen Hoddle back in 1994/95. And Pochettino is the man now charged with arresting the slide, having officially signed a two year deal on Monday.