The part about the Court possibly handing down the Dobbs decision as soon as next Monday, May 23, is not "insider information." It's simply speculation, albeit speculation prompted by the simple fact that the Court itself has most recently formally updated its calendar (available on the Court's website) to indicate that it will be releasing one or more decisions on Monday.
Could that include Dobbs? Yes. Will it? Hard to say. The second leak of information reported on by Politico, which ran the story 10 days ago, indicated that the February 10 Alito draft opinion remained at that time the only draft opinion yet circulated among the Justices. If true, this would be somewhat surprising, given the lapse of time.
This second Politico story also reported that no other separate opinions (e.g., dissents, concurrences, etc.) had yet been circulated among the Justices. If true, that would go a long way towards explaining why Alito has circulated no further draft(s); when there are to be various separate opinions (including dissents) in a case (as there surely will be in Dobbs), the Justices exchange drafts of those separate opinions among themselves, so that they can take account of, and respond if they wish, to the points being raised in those separate opinions in their own opinion.
Put simply, if the expected dissenters from Alito's "opinion for the Court" -- that is, the majority opinion -- have yet to share drafts of their written dissent(s), "slow-boating" things, as it were (perhaps waiting to see if C.J. Roberts peels off either Kavanaugh or Barrett, spoiling Alito's majority to overturn Roe and Casey?), then as a practical matter Alito is precluded from finalizing his own opinion. And who on the Court would be responsible for resolving any such conundrum? Right. Presumably, the Chief Justice.
Assuming, therefore, that the leaked information from the second Politico story from 10 days ago is true, for the Dobbs decision to come out this coming Monday, the Justices (including C.J. Roberts) would have had to have ceased their striving, circulated their separate opinions, and then finalized everything, all within the past 10 days. Possible, yes. Plausible? Meh.
A more likely release on Monday (and another decision that many have been looking for) is the Court's opinion in New York Rifle, the Amendment II case that was argued way back on November 3, 2021 (by comparison, Dobbs was argued on December 1). New York Rifle is the only case from the November sitting for which a decision has yet to be issued. Meanwhile, in addition to Dobbs, there are other five cases from the December sitting for which decisions have yet to be issued.
In short, there are plenty of things, other than Dobbs, that the Court could have on tap for this coming Monday.
Valid post, but there's the possibilty that Roberts has conferred with security and determined that if Roe was overturned on the 23rd, then the only conference day before June 2 is May 26th, and they could abandon that day, which would then give 10 days to allow the police to beat on Antifa-in-pussy-hats and 'gently disperse' the crowd.