Beto O'Rourke Beto O'RourkeJimmy Carter says his son smoked pot with Willie Nelson on White House roof O'Rourke endorses Kennedy for Senate: 'A champion for the values we're most proud of' 2020 Democrats do convention Zoom call MORE formally entered the race for the White House on Thursday, promising a “positive” campaign while saying it’s “a defining moment of truth for this country and every single one of us.”

After months of anticipation, O’Rourke enters an already crowded race filled with heavyweight contenders including Sens. Bernie Sanders Bernie SandersButtigieg stands in as Pence for Harris's debate practice Bernie Sanders warns of 'nightmare scenario' if Trump refuses election results Harris joins women's voter mobilization event also featuring Pelosi, Gloria Steinem, Jane Fonda MORE (I-Vt) and Elizabeth Warren Elizabeth WarrenHarris joins women's voter mobilization event also featuring Pelosi, Gloria Steinem, Jane Fonda Judd Gregg: The Kamala threat — the Californiaization of America GOP set to release controversial Biden report MORE (D-Mass.). Former Vice President Joe Biden Joe BidenOmar fires back at Trump over rally remarks: 'This is my country' Trump mocks Biden appearance, mask use ahead of first debate Trump attacks Omar for criticizing US: 'How did you do where you came from?' MORE is also expected to join the race.

Here are five questions O’Rourke faces in the Democratic primary:

Is he liberal enough?

Progressives have been quick to pounce on O’Rourke’s centrist-leaning positions.

The Progressive Change Campaign Committee (PCCC) immediately put out a statement saying while it made sense to support him in his Senate race against Sen. Ted Cruz Rafael (Ted) Edward CruzTrump argues full Supreme Court needed to settle potential election disputes Press: Notorious RBG vs Notorious GOP The Hill's Morning Report - Sponsored by Facebook - Washington on edge amid SCOTUS vacancy MORE (R-Texas) in 2018, his issue positions “will get more scrutiny” during the presidential race.

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“In 2020, with so many good choices like Elizabeth Warren and Bernie Sanders in the race, voters will obviously apply a lot more scrutiny to a candidate's worldview,” said Adam Green, the PCCC co-founder.

He mentioned "Medicare For all," the Green New Deal climate change plan and efforts to allow students to graduate from college debt-free as among the issues on which O’Rourke will face scrutiny.

On Medicare For all, progressives have highlighted what they say are O’Rourke’s conflicting messages.

While serving in Congress, O’Rourke described a single-payer Medicare for all program as the best way to ensure all Americans get the health care they need.

But during his Senate campaign he coined it a different way, saying Texans needed “universal, guaranteed, high-quality health care” while shying away from backing Medicare for all.

Did he wait too long?

O’Rourke was one of the hottest political brands in the country after the midterm elections when he ran a surprisingly close race against Cruz and showed off impressive fundraising skills.

Voters said he was the future of the party, and he instantly drew comparisons to former President Obama.

But O’Rourke’s star has faded a bit since those days.

He faced criticism for appearing unfocused as he took a cross-country road trip and wrote a Medium post about being “stuck” and “in and out of a funk.”

He also took his social media followers along as he visited a dentist, becoming the butt of jokes on Twitter and causing some to openly wonder if he had missed his opportunity.

There was also talk that O’Rourke might focus on a Senate campaign against Sen. John Cornyn John CornynThe Hill's Campaign Report: GOP set to ask SCOTUS to limit mail-in voting Liberal super PAC launches ads targeting vulnerable GOP senators over SCOTUS fight Senate GOP faces pivotal moment on pick for Supreme Court MORE (R-Texas).

Throughout those weeks, his poll numbers dipped.

It is entirely possible the former congressman's star will rise again.

“He faces an uphill climb in a crowded field, but he’s clearly a force that may pull enough support from today’s perceived top contenders to shake things up early on,” said Democratic strategist Zac Petkanas, who served as an senior aide on Democratic presidential nominee Hillary Clinton Hillary Diane Rodham ClintonButtigieg stands in as Pence for Harris's debate practice Senate GOP sees early Supreme Court vote as political booster shot Poll: 51 percent of voters want to abolish the electoral college MORE’s 2016 campaign.

But there are also those wondering if O’Rourke needed to more decisive about the race late last year in order to preserve the clear momentum he had at the time.

Can he win Iowa?

O’Rourke headed straight to the Hawkeye State after launching his campaign in El Paso.

The move suggests he sees a strong result in Iowa as being a key for his White House path.

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“He’s the great unknown here in Iowa,” said Pat Rynard, who runs the popular political site Iowa Starting Line. “People watched his Senate race from afar, but he didn't make any early trips so Iowans haven’t gotten up close and personal with him yet.”

Steffen Schmidt, a professor of political science at Iowa State University, said there is “a lot of interest” in O’Rourke. “He seems dynamic and charismatic and he'll get a good turnout at events.”

Petkanas said the crowded field will make the Iowa caucuses even more important.

“I think Iowa is going to be crucial for most candidates, but especially those like Beto who need at least a decent showing with the super liberal constituency that frequents those caucuses,” he said.

How much will losing to Cruz hurt O’Rourke?

Winning the White House isn’t easy, and most who do so aren’t rebounding from a political defeat in a congressional race.

Republicans have sought to use O’Rourke’s loss to Cruz as a way of defining him as, well, a loser.

“After losing his Senate bid in Texas, the Liberals’ lovable loser who has been road tripping, live-streaming, and finding himself, decided he wants to lost on a bigger stage,” a statement from the Republican National Committee blared.

Democrats may also use the Cruz loss against O’Rourke.

“If Beto O'Rourke wants to go and run for president, God bless him. He should put his hat in and make his case. But he lost. You don't promote a loser to the top of the party,” Chicago Mayor Rahm Emanuel said late last year during an appearance on MSNBC’s “Morning Joe.”

Is O’Rourke underestimated?

Being compared to Obama isn’t easy and sets a high standard for O’Rourke.

Critics say such comparisons are overblown and unfair to the Texan.

“Apart from maybe his charisma, they’re totally different people,” said one former aide to Obama.

Yet if there is a sense among some that O’Rourke gets more hype than he deserves, there are others who say it would be foolish to underestimate him.

“More than any other candidate I know so far, Beto has demonstrated that you can’t underestimate him,” said former Rep. Steve Israel Steven (Steve) J. IsraelThe Hill's Morning Report - Presented by Facebook - Trump, Biden intensify battleground focus as 2020 race tightens Biden allies express confidence as convention begins The Hill's Campaign Report: Biden closes in on vice presidential pick MORE (D-N.Y.). “He established it when he unexpectedly won his first House primary, established it throughout his tenure, and certainty when he ran against Senator Cruz. Some candidates have money, some have a good field operation. He has the proven ability to beat the odds.”

Democratic strategist Chris Kofinis agreed, pointing to the nearly $80 million O’Rourke raised in his race against Cruz.

“The simple reality is there are three things that mater: media coverage, grass roots and money, and he’s got all three. You underestimate him at your peril.”