The ability of Trump to use media and social media has transformed politics from here forward. Money is far less important than it has been at any time in the last 40 years.
Jeb can blow his $100 million and will likely have no effect. In the meantime Trump just needs to pay his security detail and keep his plane flying while he racks up the PR and coverage.
The money that Jeb has is not all for media. It’s mostly to buy people off.