With the Republican presidential nomination effectively in his pocket, Donald Trump plans to expand the electoral battleground to Maine and other states considered Democratic strongholds in anticipation of a tough fight against presumptive Democratic nominee Hillary Clinton.

But the real estate mogul and reality TV star enters the fight in Maine as an underdog. Democrats have won every presidential election in Maine since 1992, so history strongly favors Clinton.

“It’s a real long shot and a tremendous amount of resources he would have to expend for a single electoral vote,” Robert Glover, a political scientist at the University of Maine in Orono, said of the strategy.

Yet, this has been an election cycle that has defied expectations. Trump has risen to the top of the Republican field on the updraft of an anti-establishment mood among the electorate. His promises to build a wall along the U.S.-Mexico border, bar Muslim immigration into the U.S. and adopt protectionist trade policies resonate with working-class Maine voters.

Like Gov. Paul LePage, Maine’s first Republican governor in 16 years, Trump has shown an ability to defy conventional wisdom and expectations. Even with the long odds, he may have a chance to flip Maine red.

‘A fool’s errand’

The announcement that the Trump campaign would take the fight against Clinton to Maine and other states that favor Democratic candidates is consistent with the unorthodox electoral fight the Republican has waged so far.

Maine voters haven’t sent a Republican to the White House since 1988, when George H.W. Bush, who owns a house in Kennebunkport, ran to succeed President Ronald Reagan, who Mainers also backed in the 1980 and 1984 elections. Even voters in the more conservative 2nd Congressional District have backed Democratic presidential candidates.

The University of Virginia Center for Politics ranked Maine among the “safe” Democratic states in its map of potential electoral battlefields, its bluest rating.

All of this indicates Trump needs to make significant investments in time, energy and staff to flip Maine from blue to red, according to Mike Cuzzi, a Democratic political strategist.

“Maine has by no means been a swing state in over a quarter of a century,” Cuzzi said. “One has to wonder whether this is a fool’s errand to try to invest in a state like Maine and move it from blue to red.”

Attempts to reach the Trump campaign’s press office for information about its Maine strategy were not successful.

But Maine is no sure bet for Democrats either, according to Jason Savage, executive director of the Maine Republican Party.

No Maine Democrat has won a statewide race in nearly a decade. The GOP won the last two gubernatorial contests. Republicans hold the state Senate. And Republican Bruce Poliquin broke the Democrats’ nearly two-decade grip on the 2nd District seat.

A Gallup survey released in February found that Republicans in Maine have a slight advantage over Democrats. Of the surveyed Mainers, 43 percent identified as Republican compared with 39 percent who identified as Democratic, a reversal from Gallup’s last statewide survey. Voter registration data from the Maine secretary of state’s office show that Democrats outnumber Republicans by 55,000. Most registered voters are unenrolled.

Against this backdrop and with the 2nd District as a tossup, according to the Cook Political Report, Trump could have an opening to flip central and northern Maine red. (The Cook Political Report ranks the 1st Congressional District as solid blue.)

“I think Mr. Trump has a very good chance,” Savage said. “Maine has been trending Republican since 2010, and I think the 2nd Congressional District is ahead of that trend.”

Maine is one of two states — Nebraska is the other — that doesn’t award its electoral college votes on a winner-takes-all basis. So Trump could walk away with at least one of Maine’s four electoral votes in November.

No love for Clinton

When it comes to a general election matchup nationwide, Clinton is projected to easily beat Trump by a wide margin, according to a poll from Morning Consult, seizing 328 electoral votes to his 210. A faceoff in Maine, however, sees Trump with a slight edge over Clinton, though it falls within the poll’s margin of error.

“It’s apt to be [a] closer [race] in Maine than historical contests, but based on all precedents and electoral history I still think it is very much Clinton’s state to lose,” Cuzzi said.

Trump and Clinton, though, are more unpopular nationally than any other presidential candidates since at least the 1980 election, according to FiveThirtyEight. Neither candidate is particularly well-liked in Maine, either, with a poll from Critical Insights finding that 64 percent of surveyed Mainers saw Trump as untrustworthy and 55 percent thought the same of Clinton.

But in a one-on-one matchup, Trump may be able to use voter distrust of Clinton to his advantage to win the 2nd District’s electoral vote, according to Glover, the political scientist from UMaine.

“The anti-Hillary sentiment is really high and pronounced among men and rural voters and people who are struggling and feel disenchanted with the political and economic systems in this country,” Glover said. “If he just amps up that sentiment, maybe that would be enough to at least have a shot in the 2nd CD.”

Make Maine great again

On the campaign trail, Trump has tapped into Americans’ unease over free trade agreements, which many blame for the loss of manufacturing jobs in the U.S. and Maine.

A 2003 report commissioned by the Maine Legislature concluded that, while the North American Free Trade Agreement grew exports to Canada and Mexico and attracted foreign investment, Maine sustained a net loss of about 800 jobs.

Many in Maine and the rest of the country fear this will worsen under the Trans-Pacific Partnership, a proposed trade pact between the U.S. and 11 Pacific Rim nations. Trump has called it “a horrible deal” and promised to renegotiate it. This is a message that resonates deeply with Mainers who have watched five paper mills shutter in the last three years in part because of foreign competition.

“Trump has been effective at appealing to those people who have fallen upon hard times and think that there is something about our economy and political system that has sold them a bill of goods and not delivered,” Glover said.

With free trade, Trump has tapped into a nostalgia for an era when the U.S. was a manufacturing powerhouse, and he has promised to revive those industries weakened by competition from overseas.

“I think the challenge there is he has promised a bill of goods that will be equally hard to deliver,” he added.

And free trade gives Trump another opening to attack Clinton, who served as secretary of state when negotiations for the Pacific trade pact began.

Clinton previously supported the Pacific trade pact, hailing it as “ the gold standard” for free trade agreements. She has since shifted her position and now opposes it. A change of heart that will do little to shore up her support among working-class Mainers, according to Savage of the Maine Republican Party.

Cuzzi, the Democratic strategist, said economic issues will remain a major issue during the election, but the protectionist trade policies for which Trump advocates “will have the effect of hurting more people than helping lift them up economically.”

So, could Trump make Maine red again? The 2nd District, maybe. But even that appears to be a long shot. This election year, however, any attempt to predict the outcome of the presidential contest is a true fool’s errand. We’ll know Nov. 8.