Analysis: Trump's tax bill is a make-or-break moment for his political fortune

David Jackson | USA TODAY

Show Caption Hide Caption Donald Trump says he won't benefit from tax plan President Donald Trump says he won't benefit from tax plan.

WASHINGTON – For a man who centered his campaign for the White House around the promise of "winning," President Trump faces what may be a make-or-break political moment: The tax cut bill.

Signing a major tax cut into law would give Trump some political momentum as he tries to persuade lawmakers to tighten immigration rules, pass an infrastructure bill, and repeal and replace President Obama's health care law – issues that have frustrated the president throughout his first months in office.

Trump's political standing could also affect Republican prospects in next November's congressional elections.

"His brand was winning, and he needs a win," Republican political strategist Bruce Haynes said.

Trump and the congressional Republicans said they expect to secure enough GOP votes to pass a major tax bill, perhaps by the end of the year. He has repeatedly promised to deliver Americans a major tax cut and simplification plan as "a big beautiful Christmas present" – a phrase he used again during a speech Wednesday in St. Charles, Mo.

Making his latest stop on a national tour designed to sell the tax plan, Trump exuded confidence to supporters in Missouri, which just happens to be the home state of Democratic Sen. Claire McCaskill, who faces a potentially difficult re-election battle next year.

"Right now, America’s tax code is a total dysfunctional mess," Trump said at one point. "The current system has cost our nation millions of American jobs, trillions and trillions of dollars and billions of hours wasted on paperwork and compliance."

Tying proposed tax cuts into his frequent criticism of international trade deals, Trump said that reducing rates will help businesses keep jobs in the United States. Invoking a favored campaign theme, Trump said that "a vote to cut taxes is a vote to put 'America first' again."

More: As Republicans seek 50 votes for tax bill, here's what's in play

Related: Deal-making moves Senate Republicans closer to passage of tax reform bill

The president also hit another frequent campaign note, telling supporters there would be so much "winning" on his watch they would get tired of it.

"I used to say that," Trump said. "I had a lot of fun with that."

Many politicians believe that, as in other areas of life, success breeds success. Yet the inability to pass a tax bill could create a whole new set of political problems for Trump and will complicate the rest of his agenda. It would likely revive internal feuds between the maverick president and congressional Republicans, particularly Senate Majority Leader Mitch McConnell.

"He’ll take all the credit if it’s enacted and none of the blame if it fails," said economic analyst Stan Collender, professor of public policy at Georgetown University. "The success will be his, the failure will be McConnell’s and the Senate Democrats’ fault."

During his speech in Missouri, Trump disputed the idea that Republicans failed to pass a new health care bill, saying they came up just short and will try again after the tax package. "Some people said you failed with health care," Trump said. "What do you mean we failed? We didn't fail"

Trump: Tax cuts 'rocket fuel' for economy President Trump is calling the latest Republican tax plan 'rocket fuel for the economy,' adding that the new bill would cost him a fortune and has proven unpopular with the wealthy. Trump spoke at an event in St. Charles, Mo. on Wednesday. (Nov. 29)

Some Democrats, meanwhile, said Trump should be careful what he wishes for on taxes. They said the proposed Republican bill benefits only the wealthy, actually costs the middle class, and will wind up hurting GOP candidates at election time.

Jesse Lehrich, communications director with the Democratic-leaning Organizing For Action, challenged the "conventional wisdom" that failing to pass tax cuts would be a "political disaster" for the Republicans.

Passing it would be politically toxic, he said.

"It's already about as unpopular as any 'tax cut' proposal can be, and were it to become law, millions of middle-class families would soon learn they're taking home less money to subsidize billionaires and big corporations," Lehrich said.

The Republican-run Senate is expected to vote on a tax cut bill later this week. If they pass it, Senate Republicans will have to work out the differences between their version and the tax bill that House Republicans approved earlier this month.

It is not known when, or if, a final product can be passed.

When it comes to selling the tax plan, some analysts said Trump tends to get in his own way with political distractions.

In the hours leading up to his Missouri trip, Trump tweeted not only about tax cuts, but unleashed a tweet storm that included anti-Muslim videos as well as attacks on CNN and NBC News.

Politically, tax cuts are designed to appeal to Trump's electoral base, and those voters expect a bill.

"They've made that promise," said Jennifer Duffy, senior editor with The Cook Political Report. "This is what the base expects."

If those voters are "not energized," she said, "that can hurt candidates in some places. People would have a hard time answering the question, what have you done?"

On the campaign trail, Trump often touted his business experience, his deal-making savvy, and his ability to get things done.

In the days leading up to the South Carolina primary in February of 2016, Trump told one crowd: “We're going to win so much. You're going to get tired of winning."

After falling short on a new health care plan, combined with challenges ranging from North Korea's nuclear program to the Alabama Senate race, Trump could use a political win. There's also the prospect of a government shutdown when a current spending plan expires on Dec. 8.

With the economy likely to be a big election issue, Haynes said, "it would be nice for him to be able to point to some event that he clearly owns – that he can tie to the success of the economy."