"It's like getting a bear to sell you honey..."
President Trump Surprises GOP Base—Sides with Longtime Opponent in Capital Gains Debate
[media=https://youtu.be/LVFfzrgwK5U]
By Staff Political Correspondent
July 28, 2025
In a stunning turn of events, President Donald J. Trump, who returned to the White House after winning the 2024 election, broke with expectations—publicly endorsing the position of Becky Romero, a Chicago-born Democratic policy analyst, in a heated debate over capital gains taxes on home sales. Romero has been a vocal critic of Trump, famously dubbing him “Il Duce” after the fascist dictator Benito Mussolini and "Commander-in-Thief", while staunch MAGA loyalist Jack J. Jackson, who has long supported Trump, maintained the traditional conservative line against exempt expansions.
📱 Trump’s Truth Social Bombshell
On Truth Social, Trump declared:
“Saw this woman Becky Romero going toe‑to‑toe with one of our guys on capital gains—and I have to say—SHE’S RIGHT! The cap gains exemption is outdated and HURTING our seniors...”
Sources report Romero’s dry online reply:
“Miracles happen. Even Il Duce stumbles upon a good idea once in a while.”
🎤 Exclusive Turnberry Press Q&A
Later, at Trump Turnberry, the president's golf resort in Turnberry, South Ayrshire, Scotland, Trump elaborated in a slewing press exchange:
Q: Mr. President, you just backed Becky Romero’s position on Truth Social. She's repeatedly called you ‘Il Duce’ and accused you of authoritarianism. Why are you supporting her view?
TRUMP:
“Yes. So, this woman Becky Romero going toe‑to‑toe with one of our guys on capital gains—and I have to say—SHE’S RIGHT! The cap gains exemption is outdated and HURTING our seniors... Look, I don’t care what she calls me. People say all kinds of things — many of them wrong, by the way — but even a Democrat analyst can be right once in a while. And let me tell you: a LOT of people are getting hit with these unfair capital gains taxes. Seniors, people on fixed incomes — it’s horrible. They bought a house in 1980, they lived in it their whole lives, and now the IRS wants a piece. Totally unfair. Totally fixable.”
Interview with President Trump, Part 2
[media=https://youtu.be/cYANxIy0PO8]
Q: Jack J. Jackson, a major supporter of yours, disagrees. He says this kind of reform would only help the ultra-rich.
TRUMP:
“I love Jack. Great guy. Very loyal. But on this one, I think he’s missing the big picture. We’re not talking about billionaires. We’re talking about middle-class folks in places like Long Island, Orange County, and Philadelphia suburbs. Their homes went up in value, sure, but that’s not ‘wealth’ they can spend unless they sell. And then they get punished for it.”
Q: You said ‘We’re looking at this bigly’ — does that mean this will be part of the mid-term platform for Republicans?
TRUMP:
“We’re seriously looking at it. It’s a real problem. Nobody did anything about it — not Biden, not Obama, not even Bush. But we will. I’m calling it the ‘Senior Home Protection Act’ — we’ll protect seniors from these nasty surprise taxes. That’s something even people like Becky Romero should be able to support. She might hate me, but I think we agree on this.”
Q: Do you think this issue can build bipartisan consensus?
TRUMP:
“It should. If Democrats want to get behind it, I say come on board. If Becky Romero wants to advise us on this one issue, maybe we’ll take her notes. But no guarantees — I still think she’s wrong about 99% of everything else.”
Q: Isn’t this a flip-flop? You used to criticize tax breaks for high earners and coastal elites.
TRUMP:
“No. This isn’t about elites. This is about people who worked hard, paid off their homes, and just want to retire without being gouged. And we are going to fix it for them becaues it's just plain common sense.”
Trump’s remarks echo his recent signaling that he’s “thinking about” eliminating federal capital gains on home sales—aligning with legislation proposed by MAGA-aligned Representative Marjorie Taylor Greene.
🧭 Political Repercussions: MAGA Rift?
Trump’s public rebuke of Jackson — even if couched in praise — triggered surprise and some backlash from grassroots conservatives who had echoed Jackson’s framing of the issue as a giveaway to the wealthy.
Privately, MAGA-aligned influencers expressed frustration. One social media organizer, speaking on background, said, “Jack has gone to bat for Trump a hundred times. For him to side with Becky Romero, of all people? It’s baffling.”
Meanwhile, Democrats were caught off guard by Trump’s support for one of their own, even if it was issue-specific. One DNC staffer posted, “Becky Romero getting Trump to endorse her housing policy is like getting a bear to sell you honey — unbelievable, but somehow it happened.”
🗣 Romero’s Response: “I’ll Believe It When I See a Bill”
Romero issued a cautious statement. Asked by reporters to respond to Trump’s apparent policy endorsement, Romero didn’t hold back:
“He finally got something right. I’ve been saying for years that we need to index the capital gains exemption to inflation and protect seniors who are being taxed out of their homes. If he’s sincere about fixing it, I’m all for it — but let’s be honest: I’ll believe it when I see legislation and not just another Truth Social post.”
She added, “I’ll never trust a man who tried to overturn an election and compared immigrants to animals. But if this finally pushes both parties to act on an issue hurting ordinary people, I’ll take the win.”
⚖ Summary: What’s at Stake?
Trump, after defeating Vice President Kamala Harris in the 2024 election, is the first president since Grover Cleveland with non‑consecutive terms.
He signed the sweeping so-called One Big Beautiful Bill Act into law on July 4, 2025, enacting major tax cuts, though it left capital gains rules unchanged.
Democrats, Becky Romero in particular, have argued that the $250K/$500K capital gains exemption for home sales—unchanged since 1997—is leaving many older homeowners penalized as equity outpaces inflation.
Analyst estimates show nearly 29 million households now live in homes exceeding the exemption limit, with boomers disproportionately trapped due to “stay‑put penalties.”
If this unexpected policy cross‑over truly advances—through indexing or expanding the exemption—it may represent a rare bipartisan breakthrough born from political irony: Trump siding with a Democrat critic to outmaneuver his MAGA rank-and-file over tax fairness for seniors.
[media=https://youtu.be/LVFfzrgwK5U]
By Staff Political Correspondent
July 28, 2025
In a stunning turn of events, President Donald J. Trump, who returned to the White House after winning the 2024 election, broke with expectations—publicly endorsing the position of Becky Romero, a Chicago-born Democratic policy analyst, in a heated debate over capital gains taxes on home sales. Romero has been a vocal critic of Trump, famously dubbing him “Il Duce” after the fascist dictator Benito Mussolini and "Commander-in-Thief", while staunch MAGA loyalist Jack J. Jackson, who has long supported Trump, maintained the traditional conservative line against exempt expansions.
📱 Trump’s Truth Social Bombshell
On Truth Social, Trump declared:
“Saw this woman Becky Romero going toe‑to‑toe with one of our guys on capital gains—and I have to say—SHE’S RIGHT! The cap gains exemption is outdated and HURTING our seniors...”
Sources report Romero’s dry online reply:
“Miracles happen. Even Il Duce stumbles upon a good idea once in a while.”
🎤 Exclusive Turnberry Press Q&A
Later, at Trump Turnberry, the president's golf resort in Turnberry, South Ayrshire, Scotland, Trump elaborated in a slewing press exchange:
Q: Mr. President, you just backed Becky Romero’s position on Truth Social. She's repeatedly called you ‘Il Duce’ and accused you of authoritarianism. Why are you supporting her view?
TRUMP:
“Yes. So, this woman Becky Romero going toe‑to‑toe with one of our guys on capital gains—and I have to say—SHE’S RIGHT! The cap gains exemption is outdated and HURTING our seniors... Look, I don’t care what she calls me. People say all kinds of things — many of them wrong, by the way — but even a Democrat analyst can be right once in a while. And let me tell you: a LOT of people are getting hit with these unfair capital gains taxes. Seniors, people on fixed incomes — it’s horrible. They bought a house in 1980, they lived in it their whole lives, and now the IRS wants a piece. Totally unfair. Totally fixable.”
Interview with President Trump, Part 2
[media=https://youtu.be/cYANxIy0PO8]
Q: Jack J. Jackson, a major supporter of yours, disagrees. He says this kind of reform would only help the ultra-rich.
TRUMP:
“I love Jack. Great guy. Very loyal. But on this one, I think he’s missing the big picture. We’re not talking about billionaires. We’re talking about middle-class folks in places like Long Island, Orange County, and Philadelphia suburbs. Their homes went up in value, sure, but that’s not ‘wealth’ they can spend unless they sell. And then they get punished for it.”
Q: You said ‘We’re looking at this bigly’ — does that mean this will be part of the mid-term platform for Republicans?
TRUMP:
“We’re seriously looking at it. It’s a real problem. Nobody did anything about it — not Biden, not Obama, not even Bush. But we will. I’m calling it the ‘Senior Home Protection Act’ — we’ll protect seniors from these nasty surprise taxes. That’s something even people like Becky Romero should be able to support. She might hate me, but I think we agree on this.”
Q: Do you think this issue can build bipartisan consensus?
TRUMP:
“It should. If Democrats want to get behind it, I say come on board. If Becky Romero wants to advise us on this one issue, maybe we’ll take her notes. But no guarantees — I still think she’s wrong about 99% of everything else.”
Q: Isn’t this a flip-flop? You used to criticize tax breaks for high earners and coastal elites.
TRUMP:
“No. This isn’t about elites. This is about people who worked hard, paid off their homes, and just want to retire without being gouged. And we are going to fix it for them becaues it's just plain common sense.”
Trump’s remarks echo his recent signaling that he’s “thinking about” eliminating federal capital gains on home sales—aligning with legislation proposed by MAGA-aligned Representative Marjorie Taylor Greene.
🧭 Political Repercussions: MAGA Rift?
Trump’s public rebuke of Jackson — even if couched in praise — triggered surprise and some backlash from grassroots conservatives who had echoed Jackson’s framing of the issue as a giveaway to the wealthy.
Privately, MAGA-aligned influencers expressed frustration. One social media organizer, speaking on background, said, “Jack has gone to bat for Trump a hundred times. For him to side with Becky Romero, of all people? It’s baffling.”
Meanwhile, Democrats were caught off guard by Trump’s support for one of their own, even if it was issue-specific. One DNC staffer posted, “Becky Romero getting Trump to endorse her housing policy is like getting a bear to sell you honey — unbelievable, but somehow it happened.”
🗣 Romero’s Response: “I’ll Believe It When I See a Bill”
Romero issued a cautious statement. Asked by reporters to respond to Trump’s apparent policy endorsement, Romero didn’t hold back:
“He finally got something right. I’ve been saying for years that we need to index the capital gains exemption to inflation and protect seniors who are being taxed out of their homes. If he’s sincere about fixing it, I’m all for it — but let’s be honest: I’ll believe it when I see legislation and not just another Truth Social post.”
She added, “I’ll never trust a man who tried to overturn an election and compared immigrants to animals. But if this finally pushes both parties to act on an issue hurting ordinary people, I’ll take the win.”
⚖ Summary: What’s at Stake?
Trump, after defeating Vice President Kamala Harris in the 2024 election, is the first president since Grover Cleveland with non‑consecutive terms.
He signed the sweeping so-called One Big Beautiful Bill Act into law on July 4, 2025, enacting major tax cuts, though it left capital gains rules unchanged.
Democrats, Becky Romero in particular, have argued that the $250K/$500K capital gains exemption for home sales—unchanged since 1997—is leaving many older homeowners penalized as equity outpaces inflation.
Analyst estimates show nearly 29 million households now live in homes exceeding the exemption limit, with boomers disproportionately trapped due to “stay‑put penalties.”
If this unexpected policy cross‑over truly advances—through indexing or expanding the exemption—it may represent a rare bipartisan breakthrough born from political irony: Trump siding with a Democrat critic to outmaneuver his MAGA rank-and-file over tax fairness for seniors.
36-40, F
