I think there's an unfairness angle to it, if someone like the CTO makes the "boring" call. He then hacks maybe a few things here and there, but the one's to "sucker up" are the devs who have to program some "boring" shitty tech every day.
Most dev work is "blue collar" work, following top down business decisions. The opportunities for devs to push impactful bottom up projects for a company business are rare at best.
I have always preferred organizations where business problems-to-solve were pushed top-down rather than executive decisions. It encourages business understanding, initiatives and ownership.
Choosing boring technology doesn't have to be a top down thing, although it probably needs to have some mechanism for aligning a whole team (since 10 different "boring technologies" are no longer boring and bring along all the problems of using shiny new toys).