We're now in Mishleh 11,28 (alphabetically, we are up to ב )
בּוֹטֵ֣חַ בְּ֭עׇשְׁרוֹ ה֣וּא יִפּ֑וֹל וְ֝כֶעָלֶ֗ה צַדִּיקִ֥ים יִפְרָֽחוּ׃ One that relies on his wealth, he will fall, And like a leaf the righteous will blossom.
Rabbenu Yonah on Mishleh explains that one who relies on his wealth will fall due to his wealth, Middah kneged Middah. Like it says, “Wealth is sometimes there,” really causing owner detriment.
This doesn't mean he's going to lose his money, but his wealth will be negative wealth. Rabbi Miller's example was Charles Lindbergh, a famous pilot who flew across the world and broke records. But because of his fame and wealth, his child was kidnapped and never returned. That is case of an Osher, a wealth that can cause negativity because it’s wealth without bitachon.
Another explanation of this pasuk is that one who relies on his wealth will lose his wealth in a moment, as a punishment for the fact that he did not have bitachon. He quotes pesukim from Mishleh (5,13 and 23,5), “He'll lose that wealth in a bad way,” blink your eyes. On the other hand, וְ֝כֶעָלֶ֗ה צַדִּיקִ֥ים the Sadikim blossom like a leaf. Rabbenu Yonah points out that Mishleh is built on opposites, and the opposite of the one who relies on wealth is the one who relies on Hashem- his salvation will blossom. It’ll come out of his difficulties and challenges very quickly, like the leaf that grows before the fruit and the leaf that blossoms very quickly.
Rabbenu Yonah contrasts the wealthy man, who will fall suddenly from his honor and serenity because he relied on his well, with the Sadik who will be saved from his challenges very fast because of his reliance on Hashem. He reiterates that the way of Mishleh is to show opposites, the good path and the positive that comes from it, and the opposite path that comes to the negative.
The Gaon of Vilna says that this doesn’t only apply to wealth. It's just that wealth is something that people usually rely on. He explains that it says the man who relies on wealth, he will fall, but when it comes to the Sadik, it says the Sadik blossoms like a leaf. It doesn't say the Sadik will blossom. He explains with a beautiful thought: For the wealthy man, wealth is his essence. Therefore, when he loses his money, he falls, because that's who he was. That's how identified himself- with his wealth. Once he loses his money, he loses his whole identity. He loses his whole being. On the other hand, the Sadik’s wealth is not what he identifies with. It's like a leaf. A leaf is not the ikar. The leaf can fall off during the winter and grow back in the summer, and still the tree remains. The sadik may lose his leaf, which is his wealth and his external success, but that’s not his essence, that's not his identity. Therefore, he'll bounce back, as it says, The righteous fall seven times and get up.
When you fall, it's all over. But the Sadik never falls, because his essence is not the externals.
That is the beautiful diyuk of the Gaon of Vilna that
בּוֹטֵ֣חַ בְּ֭עׇשְׁרוֹ ה֣וּא יִפּ֑וֹל /one relies on his wealth, he will fall. He will fall when his wealth goes down, but the Sadik doesn't fall when his materialistic success dwindles. It's something outside of him and he remains strong.