West, the $250 million could be used to buy premiums to indemnify against losses. On that basis, the $250 million would buy more coverage, how much more would depend on the underwriter's gauging of the risk.
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The San Francisco Organizing Committee has initiated discussions with LA on putting forth a joint bid. A joint bid expands the population base from the standpoint of ticketbuyers, and ensures that all the revenue from ticket sales at all venues stays in-state.
In Boston's bid, only the finals in basketball and soccer were in/near Boston. Most of the soccer would have been played outside of Massachusetts, and basketball?
A joint LA/SFO bid would also give more choice with respect to golf courses, and baseball diamonds. And you could send the more Asian-oriented sports up to San Francisco, and play them in bigger venues.
I don't dispute that this $250M would buy double the insurance coverage that B2024 was contemplating. However, while there are many types of things that can be covered by insurance, the various industry feedback on the B2024 plan made clear that the really big gaps will never get covered. All insurers, on policies for any insured item / contract / risk category, will strictly define a baseline and will strictly exclude a long list of things. So, one type of uninsurable risk is any gap between the penciled in estimates and the actual contracts that get signed. If you thought a velodrome would be $300M and the contracts come in at $350, that $50 will be yours. Even more so, no insurer will ever insure against scope creep, in which the local committee or the USOC or the IOC or a combination of the three start adding to scope.
Those two risks come into the billions of $, and can only be averted by having trustworthy stewards in charge of the show. Insurers do NOT insure against baseline self-delusion in advance of actual contracts, and do NOT insure against scope creep.
Consider London: how many cities on this planet can you name with deeper and broader strength in the insurance industry? Either very few or none. Do you really think the organizing committee and City of London didn't have those talks with insurers? Of course they did, and I believe there were a variety of policies taken out, some of which have been called upon. But have you seen any assertions that "hey, never mind those billions of pounds of overruns, we're collecting every pence of it from the insurers?'" No such assertions are being made.
The IOC knows all this, and can explain it better than I can. Hence they demand the limitless backing of a government, the bigger the better, putting its full faith and credit and full taxing powers on the line, with absolutely no upper bounds. If a local committee has insurance, too, fine and dandy, but until the glorious day returns when the IOC is stuck with exactly one bidder for a given year, they will demand nothing less than a limitless guarantee from a government. They got it from Tokyo on 2020 (ahhh, but see the back tracking on it by PM Abe..., notwithstanding his staffers' pseudo-apology in Kuala Lumpur?). They'll get it from either Almaty or more probably Beijing (if the latter and if they really are in eco-meltdown mode, it'll be fun to watch if they pull an Abe on the IOC). It looks like at least Paris is getting ready to give it to them for 2024 (though I've got a hunch another slap down might be coming from those pesky Northern Germans, who I am sure followed the 2022-related debates down in Southern Germany).
Everything you say about the SF / LA cooperation idea sounds sensible. I lived in the SF Bay Area from 83 to 89, and relations between NorCal and SoCal were anything but sensible, up to and including talk of secession. The secession talk was each muttering darkly about seceding from the other half, not from the US, and I remember more of it from NorCal than from SoCal. It was not all in jest. Maybe it's all happy now, I don't claim to know. But, again, the way you describe it makes sense. It would warm my heart to see them get along nicely with one another.