Yet Donald Trump's campaign spokesman insists they believe he has a chance to turn Connecticut red for the first time since 1988, and that's why he is holding weekend rally there on Saturday.
Veteran Republicans, however, see Trump's Fairfield, Connecticut, campaign stop ares a fool's errand -- a prime example of what many worry is a political operation that takes Trump's proclivity for defying convention a step too far.
Trump has spent most of his campaign time in real battleground states: Florida, Virginia, Iowa and Pennsylvania. But with the general election now in full swing, any time spent in a solidly blue state feels atypical.
And, it isn't just Connecticut that has Republicans scratching their heads. Trump traveled to Maine last week, a state that has also been blue since 1992.
Trump campaign spokesman Jason Miller says their internal polling shows him up in Maine. Plus, Maine awards two of its four electoral votes by congressional district, of which there are two, and Trump is very popular in one of them.
Concerned Republicans say their worries go beyond the campaign's decision to send its greatest resource -- the candidate himself -- to chase one or two electoral votes in Maine, or to what they believe are unwinnable states like Connecticut. The other phenomenon perplexing veteran operatives is that the Trump campaign now has the needed money to finance television ads and ground operations -- they just don't appear to be spending it.
Spending nothing on TV ads
The imbalance in ad spending is astonishing. Since the end of the primaries, Hillary Clinton has spent $42.9 million in ads. Donald Trump has spent zero.
"They have to spend money efficiently right now to avoid getting buried by Hillary," argued Austin Barbour, a longtime Republican political operative.
"We saw this in 2012 against Obama when we were working on Romney. They were burying us with negative ads in swing states well before Labor Day. That same thing is happening with Trump," added Barbour.
Miller says the Trump campaign plans to start running television ads "soon" but declined to go further than that, saying he doesn't want to reveal internal campaign strategy.
Trump himself regularly complains about the content of Clinton's paid television ads. "They're false, they're deceptive, and they know they're false," said Trump last week in New Hampshire.
Still, he declared it too early for him to be spending money, and compared himself to an "old race horse" saying he is hanging back to see what happens.
"I think we have some pretty good ads but we don't want to go too fast. Just nice and easy," said Trump.
But many Republicans wonder what Trump is waiting for, since Clinton has used time and money to define herself, and more importantly, Trump, without much of a retort.
"Getting buried by paid media is a very real problem. There is no worse feeling on a campaign than seeing your opponent hit you in a TV and you're not responding," said Barbour.
During the Republican primaries, Trump's strategy to rely on "earned media" -- the fact that he was a celebrity candidate who deluged the airwaves with interviews -- worked. He won despite hundreds of millions of dollars spent by his opponents.
But the general election is quite different. The electorate he must reach to win goes beyond the GOP base yearning for a populist, off-beat and sometimes off-color candidate like Trump.
Some Republicans outside the Trump campaign think paid advertising could be especially helpful for a candidate like Trump, who lacks discipline, to maintain a consistent message for voters. He has spent the past three weeks creating news story after news story with decidedly off-message comments -- the biggest of which was going after Khizr and Ghazala Khan, Gold Star parents who attacked Trump at the Democratic convention.
Others, however, say they worry paid advertising is a waste of time if the candidate doesn't effectively mirror the messages in "earned media" --- what Trump says on the stump or in interviews.
Money and organization
When Trump first locked up the GOP nomination, he was a self-funder who was starting raising campaign cash from scratch. Early fundraising reports were paltry, but that is no longer the case.
Earlier this month, the campaign announced raising $64 million dollars in donations for July, mostly in conjunction with the Republican National Committee.
And though the Trump campaign made the unorthodox decision to rely heavily on the RNC for its ground operation in battleground states, some are still alarmed at the lagging operations.
Veteran New Hampshire Republican Tom Rath, an RNC Committeeman who has been through decades of presidential politics in the Granite State, says the Trump ground game in that important swing state is minimal.
"Republicans want to see a campaign that has a clear strategic direction that reflects reality and is backed up by a disciplined message and resources," said Rath.
"While it is not too late, it is getting close to that," he added.
No Republican has ever won the White House without winning Ohio. Yet the Cincinnati Enquirer reported
this week that Trump doesn't even have an office in Hamilton County, the most crucial Republican county in the most crucial GOP state.
"The campaign has yet to find or appoint key local leaders or open a campaign office in the county and isn't yet sure which Hamilton County Republican party's central committee members are allied with the Republican presidential nominee," reported the Enquirer.
In other key states like Florida, where Trump, along with the RNC, does have staff, they are outnumbered by Democrats. The RNC says it has over 70 paid staffers and plans at least 20 offices statewide. Democrats already have 200 staffers and say they're aiming for 100 offices in Florida.
Time to change course?
Trump's low-budget approach carried him to victory in the primaries, but even he seems to now realize the general election against Clinton is quite different.
At a rally Thursday in Florida, Trump, who normally only speaks about winning, admitted he is having a "tremendous problem" in reliably red Utah
And new swing state poll numbers
from NBC, The Wall Street Journal and Marist show Trump lagging behind Clinton in four crucial swing states: Colorado, Florida, North Carolina, and Virginia.
Now, with fewer than 100 days until the election, the question is whether Trump's "hang back" strategy with his money and advertising will work -- allow him to come from behind and win the race.