Kentucky Politics Insider: Trump, McConnell Cooperate, Is Jennings Next for Senate?

A Complex Relationship Between McConnell and Trump

The political landscape in Kentucky has long been shaped by the dynamic between Senate Majority Leader Mitch McConnell and former President Donald Trump. While their partnership has had its share of challenges, it's undeniable that McConnell has played a significant role in advancing Trump's legislative agenda. This includes supporting the passage of a major budget bill that extended tax cuts and reduced Medicaid spending.

Despite this collaboration, the relationship between the two has not always been smooth. After Trump left office following his first term, tensions escalated. Trump frequently criticized McConnell using harsh language, calling him "dumb" and suggesting he had a "death wish" for backing legislation supported by Democrats. Additionally, Trump expressed frustration with McConnell's opposition to the confirmation of Pete Hegseth as Defense Secretary and Robert F. Kennedy Jr. as Health Secretary.

In private, McConnell reportedly referred to Trump as a "despicable human being" and a "narcissist," according to a recent biography. However, the relationship has seen moments of reconciliation, such as when McConnell shared a photo on social media with Trump at a White House dinner celebrating the passage of a significant piece of legislation.

Scott Jennings and the 2026 Senate Race

As the 2026 U.S. Senate race in Kentucky begins to take shape, one name that continues to surface is Scott Jennings. The conservative pundit, known for his commentary during the Biden and Trump administrations, recently addressed his potential candidacy on a conservative podcast.

Eric Bolling, the host, noted that many people have been discussing Jennings' possible run. Although the conversation has cooled as the field has narrowed to three prominent Republicans—Rep. Andy Barr, former AG Daniel Cameron, and tech entrepreneur Nate Morris—Jennings remains a figure of interest.

When asked about his intentions, Jennings was noncommittal, stating he hadn't made any official announcements. However, he emphasized that if Trump were to endorse a candidate, he would likely support that individual. "If he calls a play, we're gonna have to run it," Jennings said, adding, "I wouldn't want to run against the president in Kentucky."

Nate Morris and the Republican Primary

The Republican primary for the U.S. Senate seat has become increasingly competitive, with Nate Morris emerging as a key contender. His campaign has focused heavily on opposing Mitch McConnell, accusing him of supporting amnesty for undocumented immigrants.

Morris' latest ad portrays both Cameron and Barr as puppets of McConnell, claiming they "stuck with" him when he pushed for "amnesty." However, McConnell has consistently opposed such measures throughout his career. The reference to "amnesty" stems from his support for a bipartisan immigration reform bill in 2024, which Trump opposed. Critics argue that the bill's provisions did not include actual amnesty for undocumented immigrants.

Morris has positioned himself as a staunch advocate for stricter immigration policies, calling for a complete moratorium on all immigration for a limited time. He has also distanced himself from McConnell, stating, "I'm a Trump guy, not a McConnell boy."

The Ad War Intensifies

Morris' campaign has launched an aggressive advertising strategy, backed by a seven-figure television campaign. Meanwhile, a political action committee supporting Barr is working to undermine Morris' credibility among Republican voters. One ad focuses on Morris' business history, accusing him of being "woke" and referencing his past support for diversity initiatives. The ad ends with a strong expletive, calling Morris "full of s-."

Zach Dembo's Impressive Fundraising

In the Democratic race for Kentucky's 6th Congressional District, newcomer Zach Dembo has made a strong impression. Just three days after launching his campaign, Dembo raised over $160,000. While it's common for candidates to secure donations before officially entering the race, this amount is notable for a first-time candidate.

Dembo's fundraising success will be compared to other candidates once the next campaign finance deadline arrives in October. Former Democratic House Caucus Chair Cherlynn Stevenson and former Lexington-Fayette Urban County Councilman David Kloiber both reported strong numbers in their June 30 reports, though Kloiber's personal wealth allows for additional funding.

While money plays a significant role in politics, it's not the only factor. In 2022, Kloiber outspent Lexington Mayor Linda Gorton but still lost the election, highlighting that financial resources alone do not guarantee victory.