Sixteen years ago, the late journalist Gwen Ifill appeared on David Letterman’s “Late Show” and touted a group of emerging Black politicians, including a little-known district attorney from San Francisco who she described as a tough and brilliant prosecutor who “doesn’t look anything like anybody you ever see on ‘Law & Order.’”

“They call her the female Barack Obama,” Ifill said. “People aren’t very imaginative about these things anymore.”

Ifill’s sheepish comparison helped catapult Kamala Harris’ profile and gave her new credibility. Suddenly, national reporters were flying into the Bay Area. Donors, eager to get in early on the next Obama, crowded her fundraisers.

But the Obama label also was a burden, one that Harris still carries. During her primary run in the 2020 presidential contest and through some of her tenure as vice president, the comparison fueled questions over whether she could live up to the hype.

“In some respects, the comparisons are right,” said Ashley Etienne, who served previously as Harris’ vice presidential communications director. “What’s unfortunate is it doesn’t give those politicians room to be themselves. The constant comparison is overwhelming and exhausting.”

Just ask any basketball player declared Michael Jordan 2.0 or a singer who is dubbed Taylor Swift redux. Many become draft-day busts or one-hit wonders. And even those who succeed often find it hard to overcome the weight of expectations.

“The whole idea of ‘The Next’ anyone is foolish, but we do it all the time,” said David Axelrod, Obama’s New York-born former strategist, who can still tick off all the supposed heirs to Yankees great Mickey Mantle. “Obama was a singular talent in a particular moment in time.”

Axelrod calls the comparisons “lazy and glib and insulting.”

This week, Obama will make the first of several appearances for Harris’ presidential campaign, holding a rally in Pittsburgh. He remains the Democratic Party’s top star and one of the biggest draws in politics.

He and Harris are longtime political allies. They met when he held a California fundraiser for his 2004 U.S. Senate run, according to Debbie Mesloh, Harris’ communications director for her district attorney campaign that year, her first run for elected office.

Obama helped Harris raise money in 2005 to retire campaign debt. Their bond was cemented in 2008, when Harris broke with the establishment by endorsing Obama for president over Hillary Clinton, giving him crucial early backing when he was still an underdog.

Harris also was one of the few down-ballot politicians he helped in 2010, when she ran for California attorney general and he was president. That was the year Democrats took, as Obama put, a “shellacking” in congressional elections.

The two shared a more awkward encounter in 2013, when Obama introduced Harris at a fundraiser as the “best-looking attorney general in the country,” prompting Obama to apologize for a remark that did not land well with Harris’ inner circle.

Still, “they always had an affinity for each other because they are so much alike,” Mesloh said. “Anyone who’s grown up being different in some sort of way reflects on that experience and I think it’s a necessary part of sort of surviving.”

Both are trailblazing politicians, mixed-raced children with unusual names, whose biographies epitomize the nation’s changing face. Harris’ parents were born in India and Jamaica; Obama’s father was born in Kenya. Neither came from wealth and both had to defy doubters to become their party’s standard-bearer.

The comparison between them, however, goes only so far.

Obama made his name with soaring oratory about a collective opportunity to fulfill America’s promise and a memoir that was deeply introspective about his role in that fight. He learned politics as a community organizer in Chicago, from the outside in.

Harris came up politically from the inside, as a prosecutor and state attorney general who tried to balance the demands of outside activists with the responsibilities of representing the establishment and the need to court police unions. She is averse to public introspection, spending far more time in her memoir reciting autobiographical details than dissecting them.

And her speeches, although designed to uplift, have been aimed at making the case that she will not be too transformative.

“I will be a president who unites us around our highest aspirations,” she said at the Democratic National Convention in Chicago. “A president who leads and listens, who is realistic, practical and has common sense.”

Her attempts at Obama-style rhetoric have often fallen flat. “You exist in the context of all in which you live and what came before you,” has become a favorite line to mock among her detractors, who say her more philosophical appeals amount to word salad.

Mesloh believes Harris’ natural rhetorical style is more lawyerly, when she can deliver a methodical case as if cross-examining a witness in front of a jury. But she has also seen Harris connect in more personal ways to people who lost loved ones in homicides, who often demanded to speak with her directly.

Harris is hardly the only politician to get the “Next Obama” treatment. Ifill, back in 2008, named several other Black politicians, including Sen. Cory Booker of New Jersey, who was then the mayor of Newark, and then-Rep. Artur Davis of Alabama, who is no longer in politics. More recently, Maryland Gov. Wes Moore has been compared to Obama, as has Pennsylvania Gov. Josh Shapiro, a rare white politician to earn a mention.

“It’s one of those comparisons that is helpful when people are saying it about you or your candidate, but it’s not necessarily the type of thing that she or someone on her staff would feel comfortable going around outwardly advertising,” said Brian Brokaw, who led Harris’ 2010 attorney general campaign.

Harris brushed off Obama comparisons in a Politico story that speculated about her presidential ambitions just weeks after she won statewide office for the first time.

“It’s flattering,” she told the outlet. But “these comparisons make me uncomfortable because I know what I want to do. I am really excited about being attorney general.”

Since former President Donald J. Trump announced his 2024 candidacy, his campaign has promoted dozens of contests for supporters to win signed merchandise or “V.I.P.” trips to meet Mr. Trump. It has offered adherents myriad “exclusive” opportunities to join clubs to give counsel to Mr. Trump, and it has repeatedly claimed that Mr. Trump is personally reviewing lists of small donors.

But most of the contests seem to have no winners, and the campaign did not confirm or provide evidence that the club members have had any opportunity to advise the former president or that Mr. Trump is paying any attention to small donor rosters.

The New York Times looked at some 7,400 emails sent by the Trump campaign since Mr. Trump entered the presidential race. About one-third of the messages dangled an incentive to entice recipients to make a small donation.

The Times also reviewed campaign emails from the Democratic candidate and former candidate: Vice President Kamala Harris and President Biden. Combined, they have sent just over 1,600 emails since Mr. Biden declared his candidacy in April 2023.

Ms. Harris, and before her Mr. Biden, have far outpaced Mr. Trump in fund-raising this cycle, including from small-dollar donors. About $454 million in donations under $200 has come into the Biden and Harris campaigns, more than double what the Trump campaign has made.

While one-quarter of the Biden-Harris messages offered donation incentives, there were far fewer options: nine contests, two memberships, chances to be listed on a wall of donors at Mr. Biden’s former campaign’s headquarters in Delaware, and about three dozen unique pieces of merchandise from the official campaign store.

Whether they are written by Mr. Trump himself or by members of his staff, as is likely the case, the tone of the emails is generally consistent with Mr. Trump’s manner in public appearances and on social media: both chummy and alarmist.

To be sure, emails using sensationalistic language, and even manipulative tactics, are not unique to the Trump campaign. A study published in the journal Big Data & Society of thousands of political emails sent during the 2020 election cycle found that — in order to nudge recipients to open emails — campaigns frequently use subject lines that include clickbait or give the impression that a message is a continuation of an ongoing conversation. The Trump campaign has used these techniques, sending emails about joining its “Deadline Donor List” with subject lines like “Alert: (1) New Message – Action Required” and “Confirm Payment Information.”

Mr. Trump’s campaign team may not be alone in some elements of its email strategy. But both in sheer number (about 75 emails per week, on average, throughout this campaign cycle) and in syntax, the former president’s campaign emails stand out. They swing wildly between doomsday tirades and deeply affectionate language — then, often, dangle a sweetener to donate.

A missive sent in May, for instance, ticked through a short list of Mr. Trump’s current grievances: “the ILLEGAL RAID on my beautiful Mar-a-Lago,” “the RIGGED BIDEN TRIALS forcing me off the campaign trail,” and “the RUTHLESS ATTEMPTS TO SILENCE MAGA & DESTROY AMERICA.”

But that was not all that was on Mr. Trump’s mind. “You are the reason I wake up every morning. I love you to the moon and back, and I really mean that,” he wrote. “So before the day is over, I want to see your name as a member of the first ever TRUMP DIAMOND CLUB.”

Enter to Win (Maybe)!

Sweepstakes are a near-constant fixture of Mr. Trump’s campaign email corpus. In the 673 days of Mr. Trump’s current candidacy covered by The Times’s analysis, his campaign ran at least one active contest — and sometimes several simultaneously — for 446 of them.

Most of the Trump campaign’s contests have promised once-in-a-lifetime experiences: V.I.P. trips to Mr. Trump’s private resorts, campaign rallies and fund-raising receptions. Contest prizes have included round-trip airfare, hotel accommodations, and a photo with Mr. Trump for the winner and a guest, with approximate retail values running up to $24,000.

A smaller handful of sweepstakes have offered memorabilia like signed MAGA hats, autographed footballs and even the American flag displayed on stage during Mr. Trump’s speech at the 2024 Conservative Political Action Conference.

In all, the combined approximate retail value of the contest prizes offered by the Trump campaign since Mr. Trump announced his candidacy totals more than $180,000.

The Times could not verify that a vast majority of that value has made its way to Mr. Trump’s supporters. Similar questions have arisen about contests Mr. Trump’s campaign and political action committee have run in years past.

The Times sent the campaign a detailed list of every contest it had promoted in fund-raising emails from Nov. 15, 2022, to Sept. 16, 2024, and asked the campaign to confirm that each contest had a winner and to provide the names of the winners. The Times also asked the campaign to provide photos of the winners with Mr. Trump in cases in which a photo was part of the prize, and a link to a “personalized” Christmas message from Mr. Trump offered as a prize in December 2022.

The campaign did not confirm that each contest had a winner. It also did not provide winners’ names, photos or a link to the Christmas video.

In several emails to subscribers since late August, the campaign has included two photos it said were of contest winners: a man named William McGuffin and his son, as well as another pair whose names the campaign did not provide. A Times review of local news and social media sources did not find winners for any of the other 39 contests.

The campaign provided two statements: one by Mr. McGuffin and one by a campaign adviser. Mr. McGuffin said that he and his son went to their “first and only political rally” on May 1, and then received a call on May 3 saying he had won a trip to Formula One’s Miami Grand Prix for a “private meet and greet” with Mr. Trump. Mr. McGuffin confirmed in a phone call with The Times that he and his son had met Mr. Trump.

In addition to asking the campaign about contest winners, The Times reviewed local news and social media posts for evidence of winners beyond Mr. McGuffin and did not find any additional winners. It remains possible that each of these more than 40 contests had a winner. But if they did not, the Trump campaign may have crossed a legal line.

Contests like the ones both campaigns have run are legally considered sweepstakes, which are a regulated category. Federal Election Commission regulations allow political committees to run sweepstakes, but do not specify the rules under which they are run. In the absence of such rules, sweepstakes regulations from federal and state regulators should apply, according to campaign legal experts.

“Sweepstakes rules should be crystal clear about whether a sponsor will award all prizes or whether a sponsor will choose alternate winners if the original potential winners are disqualified,” Kyle-Beth Hilfer, an advertising and marketing law attorney in New York, said in an email. “Any ambiguity could lead to a legal challenge from an entrant or even a regulator.”

The Harris campaign provided The Times with the names of winners for six of its nine contests. The remaining three are still ongoing or the campaign is working out timing with the winners, it said.

Exclusive Promises of Access

Supporters who sign up for Trump campaign emails can feel like they are just a click away from being in Mr. Trump’s inner circle.

An email sent soon after Mr. Trump announced his candidacy, and signed “Trump Fundraising Director,” dialed up the urgency — and the personal appeal, suggesting Mr. Trump had repeatedly asked about the email’s recipient. “We are all counting on you,” it said. “We expect to hear from him any minute, so you MUST HURRY. We know he is going to ask about you. AGAIN.”

“I am honored to invite you to become an Official Trump Campaign Cabinet Member,” the former president wrote in dozens of emails from Dec. 9, 2022, to Jan. 24, 2023. “I am only inviting a very small and select group of Patriots to join me.”

The so-called Cabinet would provide Trump and his team with “valuable insight and advice as we make some of the most important decisions leading up to the 2024 Presidential Election and BEYOND,” he added.

“Do you need a job?” Mr. Trump asked in the subject line of an offer to join his “Official Advisory Board.”

“I’m opening up a few spots on my team, and one of them is reserved just for you,” Mr. Trump said.

The Times counted at least 19 different memberships, as well as dozens of promises that Mr. Trump would review names on donor lists — promises meant to encourage email recipients to donate.

The campaign did not respond to questions about the mechanisms by which any members of these groups provide advice to Mr. Trump, whether the members have ever met in person or virtually (with or without Mr. Trump), how Mr. Trump “personally” selects the people invited to join and how many people have joined. It also did not confirm or provide evidence that Mr. Trump is personally reviewing lists of small donors.

The campaign has also promised to make at least one donor list tangible in a way that must surely be a first in presidential campaign history: Emails sent from June 12 to July 11 offered donors the chance to have their names engraved onto the tail of “Trump Force Two,” the private plane Mr. Trump reserved for his running mate’s use. Dozens had been added by late July.

Platinum Cards and Christmas Sweaters

Emails from Mr. Trump have also offered more than 100 physical items as donation incentives. The campaign has furnished the hats, shirts and mugs that have long been campaign-finance mainstays — but with an unmistakable Trumpian twist. (The MAGA hat alone has proved a canvas for abundant variation; at least 30 different colors and styles have been offered.)

The campaign has also ventured into new corners of the branded-merch universe.

The American Express Black Card, for instance, is famously available by invitation only — but the Trump Black Card can grace the wallet of any donor willing to part with $75 per month to join the “Trump Elite Membership Program.” The Black Card is among at least five physical membership cards the campaign has offered; others include platinum and gold varieties, plus “Campaign Membership” and “Trump Freedom” options.

Mr. Trump’s emails have also offered a “Personalized Trump 2024 Doormat,” an “Official Trump MAGA Cooler,” “Exclusive Trump Christmas Stockings,” “Official Trump Golf Balls” and more.

The campaign quickly churns out new items of merchandise after Mr. Trump makes news. An “I Stand with President Trump” T-shirt was available within a day of Mr. Trump being indicted by a grand jury for falsifying business records related to the reimbursement of hush money paid to cover up a sex scandal.

Email offers for T-shirts and mugs with Mr. Trump’s mug shot and the words “NEVER SURRENDER!” appeared shortly after Mr. Trump was booked on charges that he attempted to overturn the 2020 presidential election.

By December 2023, supporters could receive “Limited-Edition Mugshot Christmas Sweaters for FREE!” (with a campaign contribution of $50 or more).

More recently, Mr. Biden’s decision to drop out of the race and Ms. Harris’s ascension to the Democratic nomination has rendered moot some of Mr. Trump’s merchandise offerings. A number of items had been produced earlier in the race specifically to poke fun at Mr. Biden, including “Evict Biden” and “Crooked Joe” T-shirts and “Let’s Go Brandon” gift-wrapping paper, a reference to a meme involving an expletive and the president’s name.

Although the Trump campaign’s emails have frequently referred in negative, even pejorative, terms to Ms. Harris since she became the nominee, they have not yet offered any merchandise specifically poking fun at her.

From Sentimental to Surreptitious

In response to questions from The Times about the offers the Trump campaign includes in its emails, the campaign responded with a statement from a senior adviser, Brian Hughes. “President Trump and our campaign have a strong and effective fund-raising operation that includes digital platforms,” he wrote. “President Trump’s movement to save our nation inspires hardworking men and women from all over America to play a financial role in our campaign and MAGA movement.”

To encourage those donations, Mr. Trump’s email strategy alternates between scaremongering and statements of devotion to the reader that are sometimes startlingly personal, including frequent declarations of love.

At times, it has even appeared to include reverse psychology. Mr. Trump’s emails depend so heavily on a perception of intimacy that he sometimes asks his supporters not to spread the word — a highly unusual move for a political candidate.

“Please do NOT share this email,” Mr. Trump warned in an offer to accept an “EXTREMELY RARE” invitation for “PRIORITY ACCESS TO BECOME A 2023 ULTRA MAGA MEMBER” before it supposedly expired at midnight.

The campaign sent the same offer at least nine more times over the following two weeks.

Vice President Harris, during a Hurricane Milton update from the Federal Emergency Management Agency (FEMA) on Wednesday, covered her mouth and appeared to tell staff she was on a live broadcast after stumbling through a speech to the people of Florida.

President Biden and Harris received a briefing from disaster relief authorities on life-saving preparations for Hurricane Milton. The two also received the latest updates on the forecast and expected impacts for Florida.

While Biden attended the meeting from the White House, Harris and others attended virtually.

At one point during the briefing, Harris covered her mouth and appeared to relay a message to someone else.

FLORIDA TROOPER RESCUES DOG TIED TO POLE IN PUDDLE AS MILTON HEADS TOWARD STATE, DESANTIS CALLS OWNER ‘CRUEL’

“It’s a live broadcast,” she could be heard saying.

The moment came nearly 20 minutes after Harris stumbled through a speech to Floridians. She glanced down multiple times, appearing to reference notes or a script.

“To the people of Florida, and in particular, the people of the Tampa region: We urge you to take this storm seriously,” she said. “As has been said before, this is a storm that is expected to be of historic proportions. And many of you, I know are tough… and you’ve ridden out these hurricanes before. This one’s going to be different.

HURRICANE MILTON EVACUATIONS IN FLORIDA: WHAT TO PACK AHEAD OF THE STORM

Vice President Harris stumbled through a speech before later telling what may have been staff that she was on a live broadcast. (Pool)

“We ask you that by every measure understand it’s going to be more dangerous, more deadly and more catastrophic. So please listen to your local officials,” Harris added. “They know what they’re talking about. They know what they’re doing. And if you are told to evacuate, please evacuate immediately. Do not wait until it is too late.”

Fox News Digital reached out to Harris’ office for comment on the incident, but has not yet heard back.

Hurricane Milton reached Category 5 storm strength multiple times over the course of the last two days, and made landfall as a Category 3 storm Wednesday night in the Tampa, Florida area.

Forecasters warn that Milton could produce devastating storm surges up to 12 to 13 feet.