FSG is in a curious position this summer: Liverpool is on course to win the league, but John Henry will rarely have felt more intense scrutiny. That's because of the well-publicized contract position — but the Americans have already agreed the deal that was most important to them.
As things stand, all three of Mohamed Salah, Virgil van Dijk and Trent Alexander-Arnold will leave Anfield for nothing. The latter would be particularly egregious for an organization that insists it runs Liverpool sustainably, given the many millions of dollars of transfer value being left on the table.
So what is FSG playing at? Is it just neglecting Liverpool as an asset entirely and focusing on other things, like its latest ventures in the world of golf?
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There is no evidence to suggest that is the case. FSG did explore the idea of selling Liverpool in the not-too-distant past, and perhaps that contributed to letting the contract situation get this far, but the owners ultimately committed to staying put.
Even if FSG is still plotting an eventual exit route, it is in its best interests to keep Liverpool's value high. Intuitively, you'd imagine that does not involve letting high-value players leave for nothing, potentially impacting the club's future performance on and off the pitch.
That leaves the seemingly unlikely conclusion that FSG is making a calculated sporting call when it comes to the contract brinkmanship with Salah, Van Dijk and Alexander-Arnold. To explore that theory, it's worth looking at the identity of the decision-makers.
One of the first things FSG did when it heard that Jurgen Klopp was leaving was to get on the phone to Michael Edwards. It took plenty of persuasion, but he ultimately returned to the fold.
Edwards did not just want to be a sporting director again. So FSG put him in charge of all football operations, and even committed to buying another club for him.
That won't come cheap: money was clearly no object in this particular deal. FSG was ready to do almost anything to get Edwards back, showing the kind of determination that has not obviously been present in securing the futures of star players.
Because in FSG's minds, it has already bagged its key operator. Klopp might just about have won a power struggle with Edwards, but he was restored at the first opportunity, with a broader remit than ever before.
He has appointed Richard Hughes as sporting director, and together they will navigate the remaining months of this contract saga. While there will of course be some kind of budget from above, it would be no surprise to learn that FSG is broadly entrusting its experts to get on with it.
Liverpool already knows that Edwards can be ruthless, especially when it comes to older players. He will look at the data, and determine whether new deals for Salah, Van Dijk and Alexander-Arnold are the best path for the club at the sums being demanded.
If the answer is no, then it will not be popular. And the onus will then be on Edwards to set about constructing a team that can be immediately competitive, somehow replacing in the aggregate three of the best players in the world.
Can he do that? FSG must believe that he can: he was put in place precisely to make these big calls.
That's not to say that all (or indeed any) of the contract situations are doomed to end in departures. Edwards and Hughes clearly have not capitulated to the demands of Salah, Van Dijk, Alexander-Arnold and their agents, but nor have they slammed the door — they are simply negotiating on their own terms, within their own limits of what is and is not acceptable to pay.
Only the months and years ahead will show whether or not FSG has backed the wrong horse. Time will tell whether or not one of the best, most proven executives around is genuinely more valuable than the players delivering on the pitch.
But Edwards has already helped to construct one great Liverpool team. FSG knew who it wanted for the job, and it got him: it is that decision more than any other which will now come under the microscope.
