If the event horizon were like a black veil, this would be paradoxical. How can the 50th captain see all 49 captains in front of him cross that veil at the same time?
But it's not like a black veil.
The moment the 50th captain crosses the horizon, what they see is not especially different from before or after they cross it! They see a line of starships in front of them and a line behind them.
But when do they see ships in front of them hit the singularity?
(3/n)