inu-kun said:
Then I stand corrected, though it's a bit of bad writing. Continuously taking loans could have only worked if he managed to either run away before it was discovered (which was a matter of time) or got to a position of power to be untouchable. Both are unlikely and only work because a boar got lucky. And if he was caught he would have suffered in ways other characters in the series would feel going too far.
Though now Baelish becomes a master bullshiter rather than a financial wizard.
He didn't win because a boar got lucky.
Robert died because his preferred way to kill a boar was to wait for it to charge and dodge at the last second, something widely known to others, and Cersei instructed Lancel Lannister, his squire, to give him a much stronger wine than usual and to always keep his cup full. Cersei planned the accident that killed her husband. If not that boar, he would have likely kept drinking and the next one would have done him in.
Cersei did this because the honorable Ned Stark warned her he would tell Robert of the real parentage of his children. Something Ned told Littlefinger he was going to do. Alongside telling the rest of the kingdom, including Renly and Stannis, about it too.
Ned knew about the incest because Littlefinger guided him through his investigation of Jon Arryn's death, including introducing Ned to a whore and one of Robert's many bastards.
Ned became Hand of the King and went to King's Landing due mostly to Lysa Arryn's letter, in which she blamed the Lannisters for Jon Arryn's death, and he feared for Robert as well. Littlefinger got her to write that letter.
Robert asked Ned to be Hand of the King because Jon Arryn died. Jon Arryn was murdered by Lysa under Littlefinger's request.
Let us not forget about Catelyn Stark taking Tyrion Lannister prisoner, on account of Littlefinger telling her that the dagger used by the assassin that tried to kill Bran was one he lost to Tyrion in a bet. This is not true, he lost that dagger to Robert instead.
The Lannisters and Starks were always going to go to war with each other. The War of the Five Kings was always going to happen. Littlefinger made sure of that.