How do monetary donations translate into votes? Whether I give a candidate $1 or $1million, I still get only one vote; the only merit of donating money is to help my candidate make their views better known to more people, each of whom can now make a better-informed decision.
There are many cases of well funded candidates (be they self-funded or funded by small donors) failing to win elections; e.g. Michael Bloomberg and Bernie Sanders on the national stage. Despite tremendous advertising, these candidates were deemed inferior by enough voters to lose.