Needling Trump as 2028 looms: Inside JB Pritzker’s all-of-the-above media strategy

While sitting for his second Fox News interview of 2025 in late October, Gov. JB Pritzker made a plain observation about President Donald Trump, who earlier that day derided Illinois' billionaire chief executive as “weak” and “pathetic.”

“It seems like I live rent free in his head,” Pritzker told host Bret Baier on one of the president’s favorite news networks. “He talks about me all the time just spontaneously.”

Pritzker and Trump did not speak directly in 2025, but they regularly exchange barbs through television cameras and social media. Pritzker is among Trump’s most pugnacious critics and has likened his return to power to the rise of Nazism in 1930s Germany.

Never one to let scores go unsettled, Trump often punches back. And the back-and-forth has only escalated since he placed Chicago in his crosshairs. Trump first threatened to deploy National Guard troops to the city’s streets, and his administration later sent masked agents to conduct aggressive immigration raids.

Trump dropped his bid to occupy the nation’s third largest city on Dec. 31, but he teased on social media that “we will come back.”

The feud has allowed Pritzker to grow his national profile as he's used his bully pulpit to knock Trump and perhaps lay the groundwork for a 2028 presidential campaign.

Capitol News Illinois reviewed Pritzker’s schedule for the last seven years through public records requests and limited data shared by his campaign. Reporters found the 60-year-old governor did roughly 100 one-on-one media interviews in 2025, his most of any year in his tenure as governor. Of those, 81% were with national media outlets, podcasters, social media influencers or television entertainment hosts — a major uptick from early in his tenure.

MSNBC, which recently rebranded as MS NOW, is one of Pritzker’s favorites. He appeared a dozen times on the left-leaning network in 2025 — more than any other media outlet. He’s also become a favorite for national media outlets from the Sunday morning talk shows to cable news to Jimmy Kimmel’s late-night show on ABC. And he’s been the subject of lengthy profiles in top East Coast publications, spoken to NBC Chicago about his recent weight loss and shared his favorite small businesses with TikTok personalities.

Experts on political communication and people close to the governor say there’s an overarching goal to the all-of-the-above strategy: getting the Trump administration’s attention and presenting a contrasting message to American voters.

“I think we were able to put his voice in front of people, in front of places and spaces that got a lot more pickup and notice because of this broader vacuum that existed in Democratic politics,” Matt Hill, the governor’s deputy chief of staff for communications, told Capitol News Illinois.

Talking to Trump

Trump is known to consume hours of cable television as part of his daily routine, and he often shares his thoughts in social media posts or monologues before the White House press corps.

One of Trump’s more visceral attacks on Illinois’ governor came days before Thanksgiving when, unprompted, he called Pritzker a “big fat slob” during the traditional White House turkey pardon.

Pat Brady, a political communications consultant and former chair of the Illinois Republican Party, told Capitol News Illinois attacks like these are a sign Pritzker’s strategy is working. Brady has been a vocal Republican critic of Trump.

“For some reason, I think that Pritzker gets under his skin more,” Brady said. “I don’t know what exactly the reasons are, but some of the shots I’ve seen him take are very, very effective. If he’s in Trump’s head on Thanksgiving, then he’s been very effective. The most effective, I think, of any of the Democrats.”

Hill, who joined Pritzker’s team in late 2024 and was a communications staffer in former President Joe Biden’s White House, said the governor's cable hits are “a method and a tool” to speak to the White House, where a multiscreen display of the major American cable news networks is omnipresent.

When Trump took to social media in October to write that Pritzker and Chicago Mayor Brandon Johnson should be jailed for, in his words, “failing to protect” U.S. Immigrations and Customs Enforcement officers, Pritzker and his team made a “very intentional” choice to have the governor’s first interview live on MSNBC, Hill said.

In a live, on-the-street interview with MSNBC’s Jacob Soboroff at Chicago’s Federal Plaza, Pritzker looked directly into the camera and dared Trump to “come and get me” while extending his hands as if they were to be cuffed.

“The sitting governor of one of the largest states in America that you just threatened to arrest responding in real time on cable — that gets noticed in that building,” Hill said, referring to the White House.

Pritzker and his team have fought to wrestle control of the national narrative about Chicago away from Trump as the president threatened military deployments to the city he called a “hellhole.”

“I know he doesn't read,” Pritzker said at an Aug. 25 news conference. “I know he doesn't listen to very many people, but I know he watches television, and so perhaps if somebody from Fox News or from Newsmax is here, they'll cover the fact that Chicago is in much better shape as a result of the work that we are doing to prevent crime.”

Pritzker employed a similar national media strategy during the pandemic, using a wave of appearances to get Trump’s attention about Illinois’ needs. Between March and May 2020, he did 28 national media interviews. In all, more than half of Pritzker’s 85 scheduled interviews that year were with outlets based outside of Illinois.

The governor’s strategy of needling Trump has opened him up to criticism, with some arguing that it places Illinois in the administration’s crosshairs, whether through frozen federal funding and threatened troop deployments to the state’s streets, among other consequences that might be avoided through a more cooperative approach.

But Pritzker and his team say their posture is shaped by their dealings with Trump during the pandemic, when — even after the governor said he would publicly praise the president — the administration failed to deliver life-saving medical equipment it had promised.

The lesson from this fool-me-once moment they say was unmistakable: Don’t cut deals with Trump and don’t expect appeasement to buy protection.

This helped inform Pritzker’s high visibility media strategy during the first year of Trump’s second term. Another influx of interviews came this past fall amid immigration enforcement operations in the Chicago region. In all, Pritzker did 43 one-on-one interviews between Sept. 1 and Nov. 13, when the U.S. Border Patrol’s top commander left the state.

By the numbers

Pritzker has sat for nearly 500 media interviews since he became governor in 2019, according to the calendar maintained by his government staff and a limited list provided by his campaign. Because campaign interviews aren’t subject to the same rigorous record-keeping laws as those tracked by his state office, the list may not be an exhaustive accounting of his interviews.

Putting aside his national media blitz during the pandemic, most interviews during his first term — 82% in 2019, 87% in 2021 and 61% in 2022 — were with Illinois-based media outlets.

While local media shrunk to 19% of his 2025 media appearances, Pritzker’s staff says Illinois reporters remain a priority. The governor took questions at 70% of his public events this year, Hill said, and most influencers he speaks to are from Illinois.

Still, Pritzker has gone more national — and new — in his second term. In 2025, national media accounted for more than half of his appearances.

But the largest growth area has been with social media influencers and podcasters. After sitting for only a handful of interviews combined in the first six years of his governorship, Pritzker appeared on more than two-dozen podcasts and social media influencer pages in 2025, accounting for 24% of his scheduled interviews.

The shift reflects the rapid change in the media landscape during Pritzker’s tenure. For instance, the governor held 23 meetings with newspaper editorial boards during his first 14 months in office. Most of those no longer exist, while “new” media sources are now a regular part of his schedule.

“One of the things that we’ve come to recognize over the last seven years that I’ve been in office is the evolution of media and the need to get to a lot of different types of media to reach a broader audience,” Pritzker said at a news conference in early December. “Sometimes a podcast can have more viewers than a broadcast television station.”

Ben Epstein, a DePaul University professor who researches political communication, said the diversification of Pritzker’s media portfolio reflects the increasingly fragmented media landscape but also the importance of the methods of delivery.

An appearance on a late-night talk show or podcast matters in its own right, Epstein said, but “they’re more important when they’re cut up into splices and then spread through social media or rebroadcast.”

Anne Caprara, Pritzker’s longtime chief of staff, told Capitol News Illinois more bluntly that the change reflects the reality that people “go home at night, lay in bed and start scrolling through Reels or TikTok.”

“It’s the only way to reach people anymore because the truth is, they just don’t sit down and watch the evening news (and) they don’t wake up in the morning and fold open a newspaper that got delivered to the doorstep,” Caprara said.

Pritzker’s engagement in new media increased after the 2024 election, she said, acknowledging that Trump’s dominance in those spaces was a major factor in his victory and his gains with younger voters.

“If you're not willing to engage in that environment, then you're not really engaging in the campaign and political world as it is today,” she said.

That said, traditional media remains a mainstay on the schedule, too, which the governor’s staff attributes to a flood of interview requests from outlets both near and far eager to talk to one of the most prominent elected Democrats in the Trump era.

A review of Pritzker’s schedule over the years reveals his most-favored outlets. In Illinois, Pritzker has sat with the Chicago Sun-Times 18 times, Chicago Tribune 15 times and Crain’s Chicago Business 10 times.

Downstate, he appeared most regularly on WJPF in Carbondale. Pritzker called in to Tom Miller’s morning drive radio show 13 times before Miller signed off in October after 45 years on the air. Pritzker also sat for eight interviews with WVON — Chicago’s largest African American news talk station.

Nationally, Pritzker appeared on CNN and MSNBC about two-dozen times apiece. His next most-frequent stops were 15 times with The New York Times and 14 times with the Washington Post. Reflecting his sensitivity to the financial markets, Pritzker was interviewed by Bloomberg a dozen times.

Though he sat for two interviews with conservative Fox News, the governor has kept his media appearances to friendly settings like left-leaning MS Now, liberal podcasts like Pod Save America and influencers who create minimal political content. The strategy stands in contrast to other Democrats such as California Gov. Gavin Newsom, who has sat down with some of right-wing media’s most prolific figures such as Sean Hannity and Steve Bannon.

Positioning for 2028

Those close to Pritzker insist his communication strategy has nothing to do with presidential ambitions. Pritzker often deflects questions about his national aspirations, insisting his focus is on governing Illinois and winning reelection in 2026.

But his place in the national political scene is growing more prominent.

Brady said the president has handed Pritzker a platform.

“I think Trump is the best thing that ever happened to Gov. Pritzker insofar as building his national brand and his national identity because he provides a very calm response to some of the craziness,” Brady said.

Brady observed Pritzker is “using Trump to raise his own named ID and stake himself out as a progressive, but a commonsense progressive” by being a “happy warrior.” He thinks Pritzker’s focus on “live issues” such as immigration gives him an advantage among possible 2028 Democrats.

But unlike Newsom and Kentucky Gov. Andy Beshear, another possible 2028 candidate, Pritzker has not launched his own podcast.

Pritzker, an heir to the Hyatt Hotel fortune with a net worth estimated at $3.9 billion by Forbes, self-funded his first two campaigns for governor to the tune of more than $330 million. He’s already tapped his personal wealth again for his 2026 reelection bid and could do so for a presidential run.

Though Pritzker will never have a lack of paid media, experts say money can’t buy authenticity — making earned media critical to building goodwill with voters.

“His media strategy is not driven by money concerns. He's not Mamdani in that way,” Epstein said, referring to New York’s media-savvy mayor, Zohran Mamdani. “But he's doing things on a more national basis because all politics is more national now.”

Epstein, the DePaul professor, pointed to Pritzker’s less overtly political media appearances, which he said help humanize the governor, including a segment on Comedy Central’s “The Daily Show” that aired during the week of the 2024 Democratic National Convention. In the segment, Pritzker took correspondent Jordan Klepper on a Wrigleyville bar crawl that ended with the pair downing a shot of Jeppson’s Malört, the notoriously bitter Chicago-made liqueur.

“It's clear that in 2025, however many people that are like, 'I can't believe Pritzker went on there and did a shot of Malört,' there are way more people that are like, 'Oh, this is a real person who sort of gets me, or at least can talk to what I'm interested in,’” Epstein said.

Pritzker, Epstein said, “has this interesting story to tell because he's this exceptionally wealthy person who has always been embedded in working class politics.”

“He also is unafraid to tell it,” Epstein said. “And we're living in an environment where we're as polarized and as partisan as we have been, and media is shaking up more dramatically than I think it has been any time since maybe the introduction of cable television. So it's really interesting. It's a media strategy and a political strategy.”