Who does he owe all that money to?

 From the Democratic Underground:

Samuel Pepys on plague and fire

Samuel Pepys, 1666

From Claire Tomalin's Samuel Pepys, The Unequalled Self:

1665 was the year of the great plague in London. Pepys had heard rumours of its approach; it was in Amsterdam in 1664. Plague was in any case endemic in London, and severe outbreaks were expected every few decades: 1593, 1603, 1625, 1636 had all been bad years. In 1625 40,000 Londoners died, and a look at the parish registers shows deaths attributed to plague in almost every year of the century up to 1665.

The rich could not count on being spared, but they usually left London when the plague was virulent; and since it was carried by a particular flea and fleas proliferated in town, getting away was certainly the best move. This is what the court and almost everyone else who could afford to do so, including many doctors and clergymen, did.

The poor were the expected victims, squashed into their low-ceilinged, unaired rooms, their meagre, piled-up lodgings, narrow courtyards, alleys and streets. For most of them it was impossible to give up their occupations and move away...

The Great Fire of London in 1666:

He[Pepys] saw that the fire was being driven by the strong easterly wind, and that the dry summer weather had made everything combustible; and he decided to take action. This is when he instructed his boatman to take him to Whitehall, where Sunday service was in progress in the chapel. 

He went straight up to the king's closet and started telling people about the fire. It seems that no one had yet heard of it, and word was quickly taken to the king, who sent for him. Pepys told him what he had seen and advised him and the duke to order the blowing up of houses to stop it spreading further, telling them that the destruction of houses in the path of the fire was the only way to stop it.

This was his key role in the great fire of London, as the first to inform the king and the giver of sound advice. The king told Pepys to go to the lord mayor with the command to have houses pulled down and the promise of soldiers to help.

Pepys set off back towards the fire in a borrowed coach...they drove as far as St. Paul's, then walked on eastwards along Watling Street, meeting crowds of refugees, among them sick people being carried on their beds and into Canning (i.e., Cannon) Street, where they found the mayor, Sir Thomas Bludworth, in a state of exhaustion: "he cried, like a fainting woman, 'Lord, what can I do? I am spent! People will not obey me. I have been pulling down houses. But the fire overtakes us as fast as we can do it.'"

...Instead of returning to Whitehall for more instructions, Pepys simply walked on, fascinated by the strangeness of everything, seeing what he could see. This became his other great service, as a reporter to posterity. His description of the fire is one of the most famous set pieces in the Diary, and deservedly so...

Donald Trump: A big loser

 

From Kevin Drum:

Trump’s story turns out to be pretty simple. After screwing everybody in sight during the ’90s, he entered 2000 in parlous shape. What saved him was The Apprentice, which earned him a boatload of money and formed the foundation of his flurry of licensing and endorsement deals over the next few years. 

But as revenue from the show faded, so did Trump’s finances, and since 2012 he’s been losing money every year. Long story short, Trump has lost money at pretty much everything he’s ever done. The only exception is The Apprentice and the licensing money it enabled—which probably owes more to reality show mogul Mark Burnett than to Trump himself.