In December 2016, after winning, he returned to Mobile to say, "Thank You."
In September this year, he reportedly was interested in coming yet again, this time to whip up support for Luther Strange prior to the state's GOP Senate runoff.
Now, in December, it's reasonable to think that Trump would have Mobile on his mind one more time, perhaps to try to push Roy Moore past Doug Jones on Dec. 12.
But when Trump jets around the South on Friday and Saturday, he won't be stopping in Alabama. Instead, he'll be bookending it. He's set for a campaign-style speech in Pensacola, Florida, on Friday night before leapfrogging over to Jackson, Mississippi, on Saturday for the opening of that state's civil rights museum.
Both Republicans and Democrats suggest that it's a carefully coordinated tactic, as do political observers watching the action.
"I think he's trying to walk a fine line," said Adam Cayton, an assistant professor of government at the University of West Florida in Pensacola. "He doesn't seem concerned with the serious accusations against Roy Moore. But at the same time, he doesn't want to be seen as campaigning directly for someone who is accused of pursuing sexual relationships with teenagers."
Republicans in Alabama say Trump's move makes sense. Only 25 miles from the Alabama line, Pensacola shares an expansive media market with Alabama's coastal region and rural southwestern counties. If and when Trump speaks about the Senate race, thousands of Alabama voters will hear him.
"It's pretty smart on Trump's part to generate media for Roy Moore without actually being in Alabama," said Brent Buchanan, a Montgomery-based GOP strategist. "That's worth a couple of points for Roy Moore on Election Day."
"Every move he makes is pretty calculative politically," said Michael Hoyt, chairman of the Baldwin County GOP.
No one really knows what Trump will speak about during the rally that begins at 7 p.m. at the Bay Center in downtown Pensacola.
GOP activists expect that he'll want to discuss tax reform and the White House's wishes to recognize Jerusalem as the capital of Israel. Cayton said Trump could also highlight military spending and veterans' affairs with Navy-centric Pensacola serving as a backdrop.
But almost everyone anticipates Trump will also bore in on the Alabama election. The president, on Monday, endorsed Moore in the Senate race and has wielded his Twitter account to blast Jones.
Putting Pelosi/Schumer Liberal Puppet Jones into office in Alabama would hurt our great Republican Agenda of low on taxes, tough on crime, strong on military and borders...& so much more. Look at your 401-k's since Election. Highest Stock Market EVER! Jobs are roaring back!-- Donald J. Trump (@realDonaldTrump) December 4, 2017
Democrats refusal to give even one vote for massive Tax Cuts is why we need Republican Roy Moore to win in Alabama. We need his vote on stopping crime, illegal immigration, Border Wall, Military, Pro Life, V.A., Judges 2nd Amendment and more. No to Jones, a Pelosi/Schumer Puppet!-- Donald J. Trump (@realDonaldTrump) December 4, 2017
Said Alabama GOP chairwoman Terry Lathan: "I would assume the president will remind us all of the extreme liberal views the Democrat embraces and brags about supporting."
Bill Armistead, chairman of Moore's campaign, told The New York Times that Moore will not be at Friday's rally.
Planning for the Pensacola event has been swift. Carly Johnston, director of sales and marketing at the Pensacola Bay Center said they were first notified about the president's visit last Friday.
A Mobile rally was likely never part of the consideration. A spokeswoman with Mobile Mayor Sandy Stimpson said the city hasn't received inquiries from the White House.
Vic Knight, general manager of Ladd-Peebles Stadium - where Trump's rallies were held in 2015 and 2016 - also said he hasn't received contact from the White House. Knight said there are no activities planned for this weekend that could have conflicted with a political rally.
At least one GOP strategist who has worked with Trump - and who declined to be named -- said the White House "clearly has reservations about Roy Moore," but views his vote in the Senate as a political necessity.
Zac McCrary, a Democratic pollster in Montgomery, said Trump's decision to rally in Florida, rather than Alabama, "shows how radioactive Moore still is." He said, "Even Republicans who want to see him in the Senate have to keep an arm's length and are scared to inhabit the same space of Moore, even temporarily."
McCrary believes that the Trump trip to Pensacola will have only "marginal impact" on the Alabama race. "If Trump was barnstorming up and down the state, that's one thing. But if he's in the Panhandle or in Mississippi, it's just too clever. He's being very lukewarm on this," McCrary said.
William Stewart, a professor emeritus of political science at the University of Alabama and a longtime political observer, said, "It looks like the president wants to get close, but not too close, to Moore."
Sam Fisher, a political science professor at the University of South Alabama, said Florida visit allows Trump -- who boasts of his negotiating skills - to hedge his bets. Trump wants to campaign with winners, and polls show it will be a close election Dec. 12.
"He can distance himself if things go wrong in terms of Jones winning," said Fisher. "He could say, 'Well, I was in Pensacola and away from things.'"