> I was once even part of a vendor assessment that was rejected and it turned out that the CEO had already given the green light and signed paperwork weeks before

I worked at a place where without any of the tech staff knowing about it, the CEO literally signed a $600k/yr Adobe Experience Manager contract on a golf course with the Adobe Salesweasel, and it didn't get used at all. As far as anyone knows that bill got paid for two more years before that same CEO flew the whole company into the ground leaving ~100 people not only out of work, but unpaid for their last month and without their last 3 months worth of entitlements paid.