Chapter 1095 may have revealed the Reason why Roger laughed at Laugh Tale
In Chapter 1095 we see a tournament held by the Celestial Dragons in God Valley. Their goal was to kill all the people on the island and some of their troublesome slaves, and then claim the island and its rich resources in the name of the World Government. In one panel we see a bunch of chests that are likely rewards for the tournament. The chests are identical to the one that held the Gomu Gomu no Mi devil fruit from Chapter 1, so it is easy to assume that these chests contain devil fruits, which are rewards for the tournament.
We know that during the God Valley incident, Gol D. Roger was there and they found little Shanks in one of the chests they have stolen from the island. It is likely that the chest he was found in was one of these devil fruit chests. Someone could have removed the contents and have placed Shanks in the chest for safety during the incident.
When Gol D. Roger found Laugh Tale they said he was too early. A popular theory is that they were waiting on Joy Boy and the awakened Gomu Gomu fruit. If that’s the information they found and they knew this fruit was originally in Shanks’ chest it could explain why they are laughing as it is quite a hilarious coincidence. How did they know the chest contained the fruit? It could have been marked or they could have been hunting specifically for this fruit before they came to God Valley.
This would also explain why Shanks cried afterwards and why he went on to hunt for the fruit and bet everything on Luffy once he ate it. He’d see himself as the reason why his captain could not achieve his dream and he’d see himself as not worthy pursuing the onepiece himself.
*Theory by Ayzkub3