My interpretation is this:
* Sinclair (like so many insurers) didn't want to pay up and wanted to do all he could to avoid paying up. In his case this was enhanced by his own personal stake as a member of the insurance syndicate.
* Lon Di were pressuring the insurance syndicate to pay the ransom so that they could recover the diamonds immediately. Lon Di's main immediate incentive was not so much recovering the diamonds as avoiding the adverse publicity that was likely to flow from the theft being discovered. That was why they were keen to pay the ransom immediately rather than let the investigator complete his work.
* On the other hand, Sinclair wanted the investigator to complete his work. Signs pointed to a Lon Di employee being involved and he thought this would give the syndicate a pretext to refuse to pay.
* So, if the press was told, from Sinclair's perspective it removed the need for the immediate payment to keep things hushed up, and also increased his chances of avoiding payment altogether.
Therefore to answer your first question - he was trying to force the Syndicate not to pay Lon Di by removing Lon Di's urgency in paying the ransom.
Related questions - my understanding was that it was the Syndicate and not Lon Di which controlled the newspaper, therefore it was them that put the stop on the press story. (I could have this wrong.) But yes, I found the profusion of reporters didn't quite add up here - that suggested more press was involved. And yes, I think the idea was that Sinclair wasn't thinking straight when he selected the paper to leak to. Maybe he did know that but didn't think of it. And by the time he found out, the Syndicate had made its decision and it was too late. This is just one of the "strokes of luck" (like the cupcake-loving guard) that helped everything turn out OK.
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