I think people are really over-analyzing this move. I think it's motivated by prestige, not money, nor is free speech the heart of the matter. Twitter is a stagnant company. They have thousands of engineers that in the span of a decade don't seem to produce much at all, nothing visible or memorable anyway. Long-lasting Twitter problems (culture, spam, algorithm issues) never seem addressed. User growth is stagnating…
"stagnant company" Why must every company sustain boundless growth and 24-hour engagement? Change and growth for their own sake can be cancers. Twitter does what it does and people like it (as seen by the fact that they all use it), yet armchair generals cry out that twitter's refusal to turn into "not twitter" is somehow a failure of engineering and management, or some form of incompetence. So, I disagree, I guess.
The stock has gone nowhere since its IPO and Twitter has never paid a dividend. It has revenue of $5bn but cannot seem to turn a meaningful profit and is not growing.
So far it has been a massive failure for shareholders, who are the stakeholders that the board and management are actually there to serve.