How come no anonymous messenger since Wickr has taken off?

Wickr was never anonymous. Yes you could register without your phone number, but the client did nothing to prevent your IP address from ending up in the servers. (Same goes for SimpleX).

Wickr was also proprietary so it’s E2EE was never trustworthy: you had no way to check for backdoors outside very tedious reverse engineering.

What they got right was marketing, and there was a bunch of people using it to buy hard drugs. I saw it on dark web forums, others saw it too Wickr Me is shutting down December 31, 2023 | Hacker News

The actually anonymous messengers like Cwtch, Ricochet Refresh, Onion share chats and Quiet suffer from P2P messengers’ architectural limitations, like

  • no offline messages,
  • no iPhone support due to apple not allowing process forking for Tor,
  • higher battery drain,
  • low bandwidth and higher latency for communication,
  • slow file transfers, and
  • poor (video) call performance.

Pair that with less than polished UI and UX and it’s no wonder normies won’t jump out of joy to use them.