This seems like at least the fourth iteration of an Insiders type thing. Some of the benefits sound similar to various aspects of the original Insiders as well as later iterations. The Insiders was somewhat unofficial in nature. There was a minimum to go to the dinner and then donations were highly encouraged. The required amount was not near the additional $2,500, but I'd be willing to bet it raised a lot more money and this money all went to the benefit of basketball program, not to the general Patriot Club pool for all sports. It was run by volunteers headed by Brion of Brion's Grille and Coach L obviously participated and the Patriot Club/AD seemed to pretend it didn't exist at some level. There was obviously some sort of friction within the AD and/or PC about it, but Coach L put his weight behind it, so it happened. At one point, Brion handed control over to the Patriot Club (I can't remember why, might have been forced and/or when Hewitt came).
In the second iteration (the first iteration run by the Patriot Club who succeeded in ruining what it had been almost immediately) they would hold a dinner event with the coach and the team that was nice enough, just a lot more stuffy than the Insiders had been and it ceased to be much of a fundraiser, which was the main purpose of the original Insiders.
Sort of a third iteration was a very similar program to this latest one that included some one on one time with the coach at a sporting event. It was not advertised very widely and it was tailored for Hewitt to be a little more low key with fewer people per Hewitt's. I got the impression that Hewitt was sort of shy and did not like to speak to large groups of people. This was instituted, I think, like the first or second year of Hewitt's tenure. It would have been the year after Vaughn Gray initially disappeared from the court as I remember I got to ask him personally about the Vaughn Gray situation just before the start of the next season.
I am glad to see in this fourth iteration that they are really focusing on trying to raise funds for the program.