While the 2026 Midterm Elections swiftly approach, some Democrats and Republicans are already looking ahead to the 2028 Presidential Election. Founder of Podium Strategies and former Chief of Staff and advisor to the Biden White House Press Office, Yemisi Egbewole, breaks down some of the challenges facing the current Democratic Party. 

Following President Trump's press conference last week about crime in Washington, D.C., Yemisi shares her thoughts on the issue and her growing concerns about youth crime in major cities. She also describes the best candidates to look at for the 2028 Election, and why Governors may be the best bet for the Democratic Party as they look to move beyond both the Biden administration era.

 I Wish Someone Had Told Me: As youth voters grow more concerned with the state of the U.S. economy, Yemisi explains why Democrats need to change their messaging tactics when appealing to younger generations. 

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A D.C. crime crackdown, trade deals, peace summits, and redistricting battles headline American politics this week, as President Trump capitalizes on his current momentum to manage the moment. Founder of the bipartisan government relations firm Mehlman Consulting and author of The Age of Distribution Substack, Bruce Mehlman, explains why artificial intelligence wouldn't necessarily make redistricting any easier. 

He also discusses how companies and foreign countries are handling President Trump's second term.

I Wish Someone Had Told Me: Bruce describes why it is not too soon to discuss the 2028 Presidential Election. 

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While the end of summer nears, Democrats continue to push their anti-MAGA agenda, and President Trump steamrolls ahead. Founder of the Stewart Group, Don "Stew" Stewart, unpacks the current political climate, including why the nation is more divided than ever.

Stew suggests that Democrats' messaging is not helping them gain voters. He and Dana discuss potential issues that the Democrats could target and reform to address their declining popularity.

I Wish Someone Had Told Me: Dana and Stew examine states that are considering redistricting before the 2026 Midterm Elections. Will an attempt at gerrymandering help the Republican Party secure a win? 

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As the 2026 Midterm Elections approach, are Americans already making decisions for the following November? 

Democratic Strategist and Senior Vice President at The Messina Group, Ty Matsdorf, provides insight into the current state of the Democratic Party. He shares how Democrats plan to flip the majority in 2026 and whether they will remain bogged down by the policies and actions of the Biden administration. 

Ty also describes the changing media landscape and the need for Democrats to adapt their messaging and outreach strategies to appeal to right-leaning voters. 

I Wish Someone Had Told Me: Dana and Ty discuss whether questions concerning NYC Democratic Mayoral candidate Zohran Mamdani will frustrate other Democrats on the campaign trail. 

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Outkick Columnist and Host of the Getting Hammered podcast, Mary Katharine Ham, guest hosts for Dana. She is joined by Republican strategist and co-founder of South and Hill Strategies, Colin Reed, to unpack the first six months of President Trump's second term and his agenda successes, which Republicans hope will lead to economic gains. 

Mary Katharine and Colin weigh in on the current state of the Democratic Party. Colin notes they're putting themselves on the wrong side of 80/20 issues, and without a unifying message or leader, they will continue to flounder.

I Wish Someone Had Told Me: It has been one year since former President Biden dropped out of the 2024 Presidential race, and Colin explains why Americans still want answers about what happened during his presidency. 

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This week, Senate Republicans are laser-focused on getting the so-called rescissions package across the finish line. Republican strategist and Executive Vice President at Targeted Victory, Matt Gorman, breaks down the package aiming to claw back government spending. He explains that despite the previous noise surrounding President Trump and the former Department of Government Efficiency (DOGE) head Elon Musk's initiative to cut waste, fraud, and abuse, their agenda isn't complete without the help of Congress. 

Meanwhile, as the 2026 Midterm Elections inch closer, Matt describes why the GOP base will define the results. 

I Wish Someone Had Told Me: Dana and Matt highlight the discussion

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Over the weekend, President Trump celebrated many of his accomplishments throughout the past six months, including the passage of the "Big, Beautiful Bill." National Reporter and Columnist for The Washington Examiner, Salena Zito, breaks down the Trump Administration's significant achievements thus far and what she hopes to see going forward. Salena explains why the American heartland is pleased with the administration's progress and is benefiting from a recent economic shift.

Salena shares her new book, "Butler: The Untold Story of the Near Assassination of Donald Trump and the Fight for America's Heartland." She provides an insider's account of her experience on July 13th, 2024, and her phone calls with the President following his near assassination. I Wish Someone Had Told Me: Dana and Salena unpack the controversy surrounding New York City Democratic mayoral candidate Zohran Mamdani. 

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After a big win at the Supreme Court, President Trump continues to push his agenda forward, with hopes that Congress will pass the 'big, beautiful bill' by Friday. However, this big piece of legislation is on a knife's edge.

Former House Speaker Kevin McCarthy (R-CA) explains the process of reconciliation and the President's goal to prevent tax rates from increasing. Dana and Speaker McCarthy also discuss the recent Democratic primary election in New York City, where a self-proclaimed Democratic Socialist won the nomination. They question whether this reflects the future of the Democratic Party.

I Wish Someone Has Told Me: Speaker McCarthy addresses his prior concerns about President Biden's cognitive health, which is now under investigation.

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President Trump ordered strikes on Iran's nuclear facility on Saturday, adding to the involvement of U.S. forces in the Middle East. Now, Americans wait to see how the Iranian Regime will react. FOX News Contributor, Outkick columnist, and host of The Getting Hammered Podcast, Mary Katharine Ham describes President Trump's effective strike. 

On the anniversary of Title IX, Dana and Mary Katharine highlight how Democrats continue to fail women by endorsing transgender men in women's sports. Mary Katharine illustrates why President Trump benefits from his adversaries who loudly oppose 80/20 issues. 

I Wish Someone Had Told Me: Mary Katharine explains why she's revealing the truth about public sector unions. 

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Last week, Israel fired a series of airstrikes on the Iranian Regime with the intent to destroy their nuclear program; since then, the conflict has continued to escalate, as the opposing nations continue to exchange fire. Senior vice president at CRC Advisors Matt Whitlock shares President Trump's stance on the violent dispute and whether leaders at the 2025 G7 summit will call for an immediate cease-fire.

 Over the weekend, "No Kings" protests plagued cities across the United States as President Trump attended a celebratory parade in Washington D.C. for the 250th anniversary of the U.S. Army. While many Democratic leaders participated in the protests, Matt points out the party's hypocrisy that backs the "No Kings" agenda.  

I Wish Someone Has Told Me: While President Trump's tough-on immigration policies are highly favorable by those who voted him into office, the farming industry is navigating the ripple effects of ICE raids on its workforce.

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