Several prominent media reports emerged over the past week or so telling a similar story: the Trump re-election campaign is in financial trouble. On September 7, the New York Times warned of a "cash crunch" due to "squandered costs" that was forcing the Trump campaign to "slash" its advertising budget. Three days later, a Washington Post story used similar language, describing a campaign "facing tough budgetary decisions down the stretch" that has Republican strategists "alarmed" as "Democrats take over the airwaves." Politico suggested that Trump was compounding this apparent disadvantage by misdirecting his funds to target the already supportive national audience of Fox News Channel, allowing a Biden advertising barrage to court swing voters in swing states without sufficient contestation.
These articles all adopt a "WARNING: Crisis in Progress" tone that runs a bit ahead of the specific facts provided. A careful reading of the evidence reveals that the Trump campaign is far from broke (in fact, Trump raised $200 million in August, a historically staggering sum). What's really happened is that Trump's anticipated financial advantage has disappeared because Trump spent a chunk of money early in the race that is naturally unavailable to him now, and because his opponent has found even greater recent fundraising success (Biden raised over $350 million in August, a historically staggering-until-you-fall-over sum).
It's true enough that Biden is currently outspending Trump on swing-state television. But these reports also suggest that Trump's newly-installed campaign manager Bill Stepien has made the strategic decision to save money for a final barrage later in the race. Perhaps this choice is somewhat born of necessity; if the Trump campaign had no realistic limits on its financial resources, it would presumably be matching Biden right now. However, that doesn't mean the strategy will fail. Trump had an overall financial disadvantage in his 2016 race against Hillary Clinton, but his campaign actually outspent hers on television ads from mid-October onward and received considerable last-minute help as well from Republican-aligned super PACs.
The articles are also peppered with examples of supposedly wasteful expenditures by the Trump campaign. But $150,000 for airplane-towed aerial banners or $100,000 for cell phone security containers, whatever their usefulness or lack thereof, are petty cash-level sums in an operation on track to raise and spend well over a billion dollars in total. These factoids must be viewed within a particular context: there has been a change in leadership within the campaign, and the current Stepien-led regime has every reason to plant unflattering tidbits in the press about the decisions made during the tenure of predecessor Brad Parscale. If Trump makes a comeback in the final weeks, Stepien and company will gladly take credit for turning around the ship; if Trump loses, they will be happy enough to suggest that Parscale left them an unsalvageable wreck.
Even if Trump does face a financial disadvantage from now until November, this is very unlikely to be an election decided by money—especially his money. Most Americans' opinions about the incumbent, whether pro or con, are so strongly held that they will be very resistant to being swayed by advertising, and ad messages must compete with news media coverage to serve as information sources for the remaining bloc of undecided voters. Though he is being outgunned on the airwaves at the moment, Trump has already spent a lot this year on ads in both the television and digital realms, and these efforts didn't seem to exert a measurable effect on the horse race. The main Republican lines of attack since Biden became the apparent Democratic nominee in March haven't significantly damaged Biden's vote share or personal favorability rating, so it's not clear that putting more ad dollars behind the same message would make much of a difference.
Campaigns running consistently behind in the polls are always subjected to press coverage portraying them as organizationally incompetent, just as the strategists behind victorious candidates are always celebrated as political geniuses. Four years ago, media story after media story chronicled the chaotic, amateur-hour nature of the sure-loser Trump campaign (in contrast to the confident, professional Clinton operation) up until late in the evening on the night of the election, when commentators suddenly discovered that the Trump crew had been smarter and savvier than the Clinton team all along. It's obvious enough that Trump's second presidential campaign, like his first, has squandered advantages and misallocated resources. But elections are rarely decided by these factors, and it's hard to make the case that any significant share of voters won't have become very familiar with Donald Trump's campaign message by the time they cast their ballots.