Tom Steyer picked a fight Monday with the party he is hoping to represent in the 2020 presidential election, calling on House Speaker Nancy Pelosi to cancel the summer recess for members of Congress to hold daily oversight hearings into President Trump and his administration.

Mr. Steyer, a former hedge fund manager and a billionaire, has been playing catch-up since jumping into the Democratic nomination race this month.

The 62-year-old is casting himself as a populist outsider and urging Mrs. Pelosi and Democrats in Washington to take a more combative approach toward Mr. Trump.

“The Constitution is very clear: Congress has oversight over the president. So what’s their response? They’re going on vacation for six weeks. Seriously?” Mr. Steyer said. “We’re in a crisis.”

“That’s why I’m asking Speaker Pelosi to cancel summer vacation, and conduct daily public oversight hearings to hold Trump accountable for his crimes, corruption and racism,” he said. “Business as usual is not working for the American people. We need action. Now.”

Mr. Steyer has been a vocal advocate for impeachment, fathering the Need to Impeach movement that has put him on the opposite side of the debate from Mrs. Pelosi, who has resisted impeachment calls out of concern it could hurt Democrats in the 2020 elections.

Despite his wealth and liberal activism, Mr. Steyer faces an uphill battle.

He entered the race too late to be invited to the second Democratic debate next week in Detroit, where 20 of his rivals will square off over two nights.

Mr. Steyer’s first chance to share the debate stage will be at the third Democratic presidential debate in Houston in September, though the bar for qualifying will be higher, testing his ability to increase his name recognition and get people to invest in him.

To land a spot on stage, he must register at least 2% in four qualifying polls or receive contributions from at least 130,000 individual donors, including 400 donors in at least 20 states.

Mr. Steyer has tapped into his personal largesse to invest $1.4 million in a pair of television commercials introducing himself to voters and highlighting the efforts he has made since leaving the business world to “combat climate change, fix our democracy and hold President Trump accountable.”

He is also reminding voters of the investments he has made in Democratic candidates and causes.

Mr. Steyer contributed more than $73 million to Democratic candidates and liberal groups during the 2018 midterm elections, helping to financially fuel the blue wave and give Mrs. Pelosi another turn as speaker.

Still, there is much skepticism over the prospect of Democrats nominating a super-rich, aging, white man who has never been elected to political office to serve as the party’s standard bearer against Mr. Trump.

“He’s been active in the environmental movement for the last decade or so and has spent millions promoting candidates and causes, but at least by the standards of yesteryear, he’s not qualified for the nation’s top office himself,” The Los Angeles Times editorial board wrote over the weekend. “He’s earned a lot of money — Forbes estimates he’s worth $1.6 billion — but do we really believe that makes a person suited to run the country?”

“By all means, voters should be open to candidates who are not traditional career pols or who have risen to prominence in other ways,” they said. “But the idea that we should rally mindlessly behind a candidate who claims to be an outsider, and proves it by his or her inexperience, is rapidly losing its appeal.”

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