Washington (CNN)There is no bad time for a trip to Iowa and New Hampshire. Just ask the Trumps.
Multiple members of the Trump family are making trips to Iowa, the site of the critically important first presidential caucus in the presidential campaign, and New Hampshire, the state that hosts the first-in-the-nation presidential primary, on Monday.
The trips come as other Republicans -- namely Sen. Jeff Flake of Arizona and Ohio Gov. John Kasich -- mull possible runs against the President Donald Trump in 2020.
The President and first lady Melania Trump travel to New Hampshire on Monday to headline an event on combating the nation's opioid epidemic, a scourge that has ravaged the Granite State and was a focal point of the 2016 primary campaign that Trump dominated. The trip marks the first time the President will visit New Hampshire since winning the White House.
At the same time, first daughter and senior White House aide Ivanka Trump is in Waukee, Iowa, a small town on the outskirts of Des Moines, the state's capitol.
Ivanka Trump is in town to tour Waukee Innovation & Learning Center and meet with staff and students about the President's infrastructure plan, which incorporates plans to expand federal job training programs.
Both trips are for official White House events with no stated political purpose. But when it comes to trips to Iowa and New Hampshire -- even 20 months before voters in each state will pick their presidential nominees -- everything is political.
The Trump trips comes roughly 72 hours after Flake, the retiring Arizona Republican and frequent Trump critic, tested the water in New Hampshire at a Politics & Eggs event, a speaking series hosted by New England Council and the New Hampshire Institute of Politics at Saint Anselm College that has become a must-stop for any presidential candidate.
Flake raised concerns about the state of the Republican Party during his time in New Hampshire, criticizing his party for not "appealing to a broader electorate" and described Trump as a "president (who) belittles or ridicules those on the other side."
In pure New Hampshire fashion -- the state's town hall circuit is defined by incisive and direct voters -- Flake was asked by a New Hampshire voter if he planned to run against Trump in 2020 and left the door wide open.
"I hope that someone does run in the Republican primary, somebody to challenge the President," he said. "I think the odds that I will are long, but I've not ruled it out."
Flake is far from the only Republican considering the uphill climb of challenging the sitting president.
Kasich, the Ohio governor and another Trump critic, told CNN earlier this month that "all options" are on the table when his term ends next year.
"I don't know what I'm going to do, but all options are on the table, both for me in my private, my professional life," Kasich said.
Trump's political operation inside the White House has been firmly focused on the 2018 midterm elections, White House officials tell CNN.
But outside the walls of the West Wing, Trump's political operation is squarely focused on getting Trump reelected in 2020. His campaign has begun to staff up -- including by hiring a new campaign manager earlier this year -- and Trump symbolically declared he was running for re-election earlier this year, far earlier than any other modern sitting president. Trump officially filed for re-election shortly after his 2017 inauguration.
The possibility of a Republican challenging Trump in the election is high, especially if the party sustains sizable losses in Congress in 2018 and the number of Americans who disapprove of the President -- currently hovering around the 40% mark -- stays substantially lower than his approval rating.