President Donald Trump has repeatedly said he likes "winners."

But the president's support of an Alabama Senate candidate trailing in most polls has some political observers questioning why the country's chief executive wants to expend political capital in a primary fight.

Trump shook up Alabama's special Senate election with a Tweet Saturday announcing he'll stump in Huntsville this weekend for incumbent Sen. Luther Strange, who is viewed as the preferred candidate among the Senate establishment.

I will be in Huntsville, Alabama, on Saturday night to support Luther Strange for Senate. "Big Luther" is a great guy who gets things done! — Donald J. Trump (@realDonaldTrump) September 16, 2017

As Breitbart News wrote Saturday, Trump's announcement is a "a seriously risky move that has little to no upside for the struggling president."

"It is high risk," said Bruce Oppenheimer, a professor of public policy and education at Vanderbilt University in Nashville. "It is extremely rare for a president to campaign in his own party's primary beyond letting it be known that he favors a candidate. Normally, surrogates act on his behalf."

He added, "Should Strange lose, it will raise questions about his clout."

Added William Stewart, a professor emeritus of political sciences at the University of Alabama: "Yes, there is risk for Trump. There is never a dull moment with this president."

'Perplexed, confused'

Indeed, some experts believe that Trump's political capital - however it will be spent during his Saturday rally to support Strange's candidacy - could be minimal given that the president has skirted normal conventional thinking about politics since he began campaigning for president in 2015.

But the Alabama campaign offers some unique plot twists for the president: For the first time in a political fight, Trump appears to be going up against his former chief strategist in Stephen Bannon, conservative pundits and the tea party movement which all backed his candidacy for president. Those groups, including Bannon, appear to be all-in with their support for former Alabama Supreme Court Chief Justice Roy Moore.

"It's absolutely unique, but everything about Donald Trump is unique," said Gary Nordlinger, a professor of political management at George Washington University. "Conventional wisdom is why Trump is wading into a situation where he may very well embarrass himself. But conventional wisdom with Donald Trump is almost always wrong."

Brent Buchanan, a Montgomery-based political strategist for the GOP, said Trump's public spat this summer with Attorney General Jeff Sessions - considered one of Alabama's most popular politicians following a 20-year stint in the Senate - should prove to conservatives in the state that the president is "like Teflon" and is unconcerned with political norms.

"He can wade into battles, get muddy, and walk away completely clean in the eyes of voters," Buchanan said.

None of that is to say that Trump's far-right backers are not puzzled over the actions of a president whose populist "America First" movement they have feverishly supported.

Moore is the twice removed state Supreme Court justice whose social crusades for religious liberty and opposing same-sex marriage have made him a darling among evangelical voters. He is often viewed as the politician whose populist persona is more in line with Trump.

Strange, they argue, is more of the "establishment" candidate as indicated by the financial backing he's received from the Senate Leadership Fund. The SLF backs candidates closely aligned to Senate Majority Leader Mitch McConnell.

Trump first endorsed Strange ahead of the Aug. 15 GOP primary, via Tweets, but had been relatively quiet since that election. Moore was the top vote-getter with 39 percent to Strange's 32 percent.

Moore has led in almost every poll taken since the primary leading up to the runoff election on Sept. 26. The winner in the runoff will face Democrat Doug Jones during the Dec. 12 general election.

Jenny Beth Martin, chair of the Tea Party Patriots Citizens Fund, which endorsed Moore's candidacy on Monday, said she believes the president received "bad advice" ahead of the initial endorsement.

"He was committed," she said. "In that context, doing what he can to support his endorsed candidate makes sense. But he'll find, maybe to his surprise, that Roy Moore will make a more trustworthy ally in the Senate than Strange. Moore far more closely aligned with Trump on the issues, while Strange is a creature of the Washington Swamp, and Mitch McConnell's hand-picked candidate."

Dean Young, the Orange Beach developer who is close friends with Moore, said he believes Trump is getting "bad information."

Young said he's planning a counter rally Saturday in rural Washington County.

Still, Young said that neither him nor Moore are backing away from support of Trump and his agenda. "Luther is going to work for the leadership of the Republicans that are spending millions of dollars to get him elected. Moore has said he would work very well with Donald Trump."

Trump's Huntsville appearance, planned Saturday, to bolster Strange's candidacy also comes after the president, much to the chagrin of conservative pundits and leaders, appeared to have cut a deal last week with Democrats. That deal is to support a law backing the Deferred Action for Childhood Arrivals program, which provides amnesty for undocumented immigrants brought into the U.S. as children.

An NPR story on Monday, however, indicated that social conservatives who have backed Trump may be undeterred. Speaking to a group of Trump voters in Iowa, NPR noted that they are still more likely to back the president than his conservative critics.

Said Young: "You are not going to see Judge Moore lift his hand against Donald Trump. We agree with him on what he's done and what he ran on. But I get it all the time from people on why did Donald Trump (back Luther Strange)? They are perplexed and confused. Your common, every day voter is confused."

'Tactical response'

Some political observers believe there could be a strategy underscoring Trump's Alabama visit. Among the theories tossed out is that the president is attempting to send a message to Bannon.

Other observers view Strange as the loyal "team player," whom the president trusts. The location of the rally could also be a factor since it's in the backyard of U.S. Rep. Mo Brooks, who endorsed Moore's candidacy on Saturday.

Nordlinger believes Trump may be sending a message to Bannon, his former chief political strategist, that the president will not be politically intimidated by his tinkering in congressional elections.

Bannon left the White House last month and, in an interview with The Weekly Standard, proclaimed that the Trump presidency "we fought for, and won, is over."

National news media reports have since suggested that Bannon is planning an aggressive effort to unseat McConnell-backed candidates in the Deep South and elsewhere, and replace them with insurgents who are loyal to the Trump's nationalist agenda.

Sen. Luther Strange greets supporters as they wait for the election results at a party, Tuesday, Aug. 15, 2017, in Homewood, Ala. (AP Photo/Butch Dill)

Bannon's first attempt appears to be in Alabama, where a group called the "Great American Alliance" is planning a last-minute push to back Moore. The group's senior adviser is Andy Surabin, who served as Bannon's political consultant while the two were in the White House together. Former Alaska Gov. Sarah Palin, a Moore supporter, is expected to campaign for the ex-judge this week.

Bannon rejoined Breitbart on Aug. 18, the day he left the White House. The popular conservative news site has posted a host of articles supportive of Moore and critical of Strange in recent weeks.

"I really think that this is not strategic thinking on Donald Trump's part," said Nordlinger. "Rather, it's a tactical response that he's showing Bannon he won't be intimidated by him."

Bannon aside, Trump's appearance to support Strange could simply be viewed as a supportive nod toward a politician the president views more as a "team player," said Stewart, the former political science professor from the University of Alabama.

Strange, in advertisement throughout the campaign, claims he is a strong backer of Trump and his agenda, which includes the construction of a wall along the U.S.-Mexico border.

Honored to have @realDonaldTrump's endorsement. He's all in. He wants someone in Washington he can work with. #ALSEN https://t.co/aJbpxm181q — Luther Strange (@lutherstrange) September 17, 2017

Trump remains popular in Alabama, a state he overwhelmingly carried in November with over 62 percent support, even though his overall approval rating lingers below 40 percent.

Stewart said the closest political parallel to Trump's visit to Alabama during a primary was in 1938, when President Franklin Roosevelt visited Georgia to encourage Democratic voters to back a candidate who supported his New Deal platform. Instead, primary voters backed the incumbent senator at the time who opposed the president's platform.

The move had consequences as Roosevelt's margins of victory in subsequent elections fell considerably in Georgia.

Trump's announcement that he's going to be rallying for Strange in Huntsvillle also fell on the same day that U.S. Rep. Mo Brooks - who won two counties in North Alabama during the Aug. 15 primary - is backing Moore.

Trump visited nearby Madison during the 2016 campaign, and received his first endorsement from a sitting politician during that rally - from Sessions.

"It is no accident that the Trump appearance is in Huntsville, the media center for the Tennessee Valley and home to Congressman Brooks, who endorsed Moore," said Jess Brown, a retired political science professor from Athens State University. "Even a casual observer of elections understands that the Mobile area and Tennessee Valley will be critical to both Moore and Strange in the runoff."

But as Nordlinger notes, Trump may not be thinking about any of the consequences or traditional political calculations when he comes into Alabama to stump for Strange.

"If Luther Strange loses, people will say, 'Trump doesn't have the influence' or the 'coattails,' but I don't believe Donald Trump thinks that way," he said. "Remember, this guy has defied the political laws of gravity for the past 2-1/2 years."