The Obama Decision That Helped Pave the Way for Trump — And My Connection to It

I didn’t vote for Barack Obama in 2008. Instead, I worked on Senator John McCain’s campaign, running a field office in Mechanicsville, Virginia, a deep-red Republican district. Each night, I slept in the basement of a local political activist: Rusty McGuire. McGuire, a red-haired Army veteran with freckles, was a kind and generous host. Following the election, he set his sights on a seat in the Virginia House of Delegates. The 55th District had opened up after Delegate Frank Hargrove announced his retirement, and Rusty asked if I would manage his campaign.

At the time, I had ties with Congressman Eric Cantor (see photo above). Cantor represented the 7th District and was quickly rising through the House leadership. My connection to Team Cantor began in 2006, when I interned in his Capitol Hill office. Working closely with his Deputy Chief of Staff, Bill Dolbow, I built a database to assist Cantor’s whip operation (e.g. tracking votes and coordinating legislative strategy). Like all interns, I also answered phones, and I often heard from Ray Allen. Along with Ron Butler, Allen ran a direct mail and consulting firm called Creative Direct, which supported Republicans throughout Virginia and the country.

So when Rusty asked me to help with his campaign, I reached out to Allen and Butler. We got lunch at a burger joint in Richmond, and I asked if they’d consider consulting for Rusty. A few days later, Dolbow called me into his office and warned against working for McGuire. Dolbow said that I was risking expulsion from Team Cantor’s “circle of trust.” It turned out that Allen and Butler planned to advise John Cox, a wealthy businessman, in the contest for the 55th District.

In hindsight, the contest between McGuire and Cox marked an early flashpoint in what would become a clash between the establishment and outsider wings of the GOP. The race between McGuire and Cox was nasty, as negative mailers targeted Rusty unfairly, and a number of grassroots conservatives resented the way party elites had lined up behind Cox and vilified Rusty. (Cox eked by with just 232 votes.)

This insider-outsider tension became even more pronounced in 2011, when Peter Farrell, a classmate of mine at the University of Virginia, received the Republican nomination over Dave Brat, an economics professor at Randolph-Macon College, for another delegate seat in an adjacent district. In this instance, it’s important to mention that Peter is the son of Dominion Resources CEO Thomas Farrell II, a longtime donor to business-centric Republicans.

Brat and Farrell were among the prospective candidates who gave presentations to the leadership of the Henrico County Republican Party Central Committee. It isn’t hard to imagine that GOP activists, still upset about McGuire’s treatment, were equally frustrated by the closed-door process that elevated Farrell. That frustration simmered until June 10, 2014, when Professor Dave Brat shocked the political world by defeating House Majority Leader Eric Cantor in what remains one of the most stunning primary upsets in American history.

The fight between McGuire and Cox and the battle between Brat and Farrell foreshadowed the populist uprising that would eventually propel the ultimate outsider, Donald Trump, to take over the Republican Party. But it is also the case that Obama made a mistake in interacting with Eric Cantor that fueled the Tea Party movement, which then fueled the rise of Trump.

In 2008, while I had a window to the changing Republican Party by working in Mechanicsville, Virginia, Obama was working his political magic by putting together a broad coalition. Compare Obama’s victory in 2008 with Donald Trump’s win in 2024. To be sure, Trump won this last election decisively with 49.8 percent in the popular vote and 312 Electoral College votes. Trump also won each swing state and, as seen in this map, nearly every single precinct in America shifted rightward. But compared to Trump’s recent win, Obama cruised in a landslide, winning 52.9% of the popular vote and 365 Electoral College votes. Also, whereas the Republicans won the House and Senate by just a handful of votes in 2024, Democrats crushed Republicans in 2008 by winning 257 seats in the House and 57 seats in the Senate. But Obama didn’t just enter office with a sweeping victory. His campaign had promised to transcend partisanship and usher in a new political era.

Following Obama’s historic win, Congressman Eric Cantor was rattled. He feared that Obama’s charisma and broad mandate might fracture the GOP. Cantor expressed concern—publicly and privately—that President Obama could fracture the Republican coalition. Cantor saw Obama as a potentially transformative figure who might peel off moderate Republicans or pressure the GOP into policy compromises that would divide the party.

Anticipating the Democratic stimulus package, Cantor and other members of House leadership worked to devise an alternative, and, just three days after the inauguration, Cantor and House Minority Leader John Boehner met with Obama at the White House. Cantor brought with him a copy of the Republican plan. He expected negotiation. But Obama quickly shut him down. “Elections have consequences,” he said. “Eric, I won.” There would be no negotiation.

Obama’s refusal to be magnanimous and play ball was widely reported in many mainstream news outlets (e.g. The New Yorker, Politico, The Washington Post) at the time. But back then, I also heard it secondhand from a senior policy advisor to Congressman Rodney Frelinghuysen of New Jersey. This close friend’s father told me that Frelinghuysen might have supported Obama’s plan if the president had made more of an effort to engage. He told me that Rodney could have been pulled along by Obama.

What could have happened had President Obama treated the opposition as governing partners early on rather than slamming the door on Cantor’s offer with the “I won” comment? Given that 34 House Republicans represented districts that voted for Obama, I imagine that the world would be very different if Obama offered a genuine olive branch. By dividing the Republican ranks, he could have pulled moderates into his orbit and undercut the forces that later fueled the Tea Party. Personally, I think that more moderate Republicans would have resisted Tea Party radicalism if President Obama had taken a different path.

Obama wasn’t the only president who has missed an opportunity to define his term through the politics of negotiation rather than dominance. Donald Trump is doing that right now. As Yuval Levin of the American Enterprise Institute explains, “From the outset of the Trump Administration, Republicans gave up on the prospect of attracting any Democrats to support their legislative agenda…..If they had started by seeking a bill that could gain the votes of, say, 25 House Democrats, they could have made it easier on themselves to move a more attractive measure. They could have afforded to let a few of their own members vote against the bill, which could have served those members well at home, while also making it harder for some Democrats to oppose it.” But rather than splitting the Democrats on issues like immigration, we see the Trump pushing the Republicans to vote in lockstep and not even attempting to work with Democrats. Moreover, we see a Donald Trump who is trying to govern by attempting to take down and primary any Republican who dares cross him regardless of the issue. I think back to Rusty McGuire.

Fifteen years after I slept in Rusty’s McGuire’s “ManCave” of a basement, which had a huge television (we watched Saving Private Ryan on the eve before the election), a pool table, and several full-size arcade machines, Rusty’s brother, John J. McGuire III, a Virginian state senator from Goochland, decided to challenge Congressman Bob Good in Virginia’s 5th District. Rep. Good, it should be said, is as Trumpy as they come and was the chair of the ultra-conservative House Freedom Caucus. Still, Trump endorsed McGuire. Why? Because Good dared to endorse Florida Gov. Ron DeSantis in the 2024 Republican presidential primary. Sure enough, Trump’s endorsement was crucial, as McGuire defeated Good by 370 votes.

I don’t blame President Obama for the rise of Donald Trump. And I certainly don’t excuse the Republicans who met Obama’s presidency with racial resentment or conspiratorial fervor. Indeed, when I was working in Mechanicsville, I encountered, for the first time in my life, outright racism. I met activists who supported McCain because “Barack Hussein Obama” was a “Muslim” and “not a true American.” All I am trying to argue in this newsletter is that Trump’s rise didn’t happen in a vacuum. It occurred, in small part, because Obama brushed aside Congressman Cantor’s overture.

Barack Obama’s decision told Republicans that they were not needed. It gave fuel to the firebrands who would soon claim the mantle of the Tea Party and later MAGA. I saw the early sparks of that fire up close—in Rusty McGuire’s campaign, in the backroom deals that sidelined Dave Brat, in the resentment that festered across central Virginia. At the end of the day, Obama’s comment to Cantor revealed a deeper assumption that has increasingly defined presidential behavior in the modern era: that electoral victory entitles a president to govern unilaterally. When presidents treat elections like coronations and opponents like obstacles, they corrode the very norms that hold a diverse republic together. As I wrote last November, unlike parliamentary systems, which allow for majority rule, our system demands minority input. In short, Obama had a chance to show the country a different way. I wish he did.