Is it true that the candidate with the most money always wins?
They usually do. But—and this is an important "but"—that is true because the candidates who get the most money are usually the ones who are most likely to win. They are candidates who have proven themselves by winning other elections, earning the support of party leaders, and achieving name recognition among voters. Candidates who have never won, or even ever run in, an election will not have the full support of party leaders, will be unfamiliar to voters, will not attract much money, and are not likely to win.
But what if these unproven candidates are rich enough to pour tens of millions of dollars into their own campaigns? That usually does not work. It worked for billionaire Michael Bloomberg, who won three terms as mayor of New York City, in 2001, 2005, and 2009, by spending record-shattering sums of his own money to greatly outspend his publicly funded opponents. But it did not work for former eBay CEO Meg Whitman, who broke Bloomberg's record by giving $144,000,000 to her 2010 campaign for California governor, only to lose to the out- spent but better-known and more experienced Jerry Brown.6
Where money may matter most is when two experienced politicians face one another in an open-seat election. In a contest between two candidates who have both won elections, have the full backing of their parties, and are well known to voters, but who do not both attract the same amount of money, having a bigger campaign fund could be the deciding factor in winning the election.
Money is necessary because campaigns can be expensive, but money alone rarely wins elections. Think of running for an elective office as like playing blackjack in Las Vegas. Having a lot of money is no guarantee that you will win, but without money you cannot even get into the game.