Canon Background
https://awoiaf.westeros.org/index.php/Roland_Crakehall_

In-Campaign
When traveling members of House Jasper visited Crakehall on their northbound journey they found in Lord Crakehall a sorrowful and desperate man. He explained that his house’s silver mine had run out of ore, and through bad advice and bad judgement he lacked the funds to dig a new shaft. He explained that he was unwilling to ask Lord Tywin Lannister for the gold, lest he look incapable to the lord paramount. Terms of a loan were agreed upon with Teddy Jasper. In exchange for 200gd of his personal wealth in capital Roland will repay 600gd in one year’s time.

By the time Teddy returned to claim the return on his investment, in March of 287 AC, Lord Crakehall explained that regretable he did not have the coin. When Teddy did not appear one year later Lord Crakehall waited some time and then decided to invest in spices from the Summer Isles which he had not yet sold. Roland was able to pay 100gd to Teddy immediately as well as 50gd worth of spices. Teddy would have to return later for the remaining 500gd.