Is it deja vu all over again? In 2008, Virginia's 5th District was the site of a gigantic upset when tireless 34-year-old Democrat Tom Perriello unseated GOP Rep. Virgil Goode by 727 votes. Perriello took advantage of an Obama wave of student turnout in Charlottesville and Black voters in Southside Virginia, as well as a deeply polarizing GOP opponent who barely raised money and ran a stone age campaign.

Fast forward to 2020. Democrats have coalesced behind perhaps their most ideal House candidate anywhere: Cameron Webb, a telegenic 37-year-old physician who works at UVA's School of Medicine. Meanwhile, GOP former Liberty University athletics official Bob Good (no relation to Virgil Goode) is still struggling to unite Republicans after defeating GOP Rep. Denver Riggleman at a June drive-through convention.

It takes a perfect storm to elect a Democrat in the 5th CD, which sprawls from the North Carolina border to the DC exurbs. President Trump carried it 53 percent to 42 percent in 2016, and even in 2018, Sen. Tim Kaine lost it by two points to Republican Corey Stewart, who didn't conceal his support for Confederate symbols. In the House race, Riggleman beat liberal journalist Leslie Cockburn 53 percent to 47 percent.

But sometimes, perfect storms still happen. Earlier this year, Republicans managed to flip California's 25th CD - a district Hillary Clinton carried by seven points — by nominating Mike Garcia, a Hispanic former fighter pilot with deep community ties. 

In Webb, Democrats may have found their own "unicorn:" a young Black doctor who graduated from UVA, has treated COVID patients, whose wife (also a physician) is from rural Southside and whose father served in law enforcement for 20 years. In his ads, Webb talks about the need for bipartisanship and his experience "working for presidents Obama and Trump" as a White House domestic policy adviser. 

Meanwhile, Good, a former Campbell County supervisor, is a pure base candidate. He's a strident same-sex marriage opponent and self-avowed "biblical conservative" at a time when Liberty University's reputation has been tarnished by scandal. In his first ad, launched weeks after Webb first took to the air, he awkwardly wrestles his own son for 30 seconds and promises he'll "put liberal ideas in a headlock."

Webb and Good's routes to their party's nominations couldn't have been more different. In the June primary, Webb started off as an underdog in a four-way field that including two Marine veterans and a well-funded woman endorsed by EMILY's List. But Webb stood out as the only candidate of color. In the end, he romped by a whopping 48 points, racking up huge margins among rural Black voters in Southside.

Good launched his challenge to Riggleman in 2019 after the libertarian-leaning freshman officiated a gay wedding between two former campaign volunteers. The 5th District GOP committee opted for a drive-through convention of local party officials in the parking lot of a church in Good's home county. At 1am, Good was declared the winner with 58 percent, and Riggleman - who had decried the process - quickly called it "rigged."

Riggleman, who co-owns a distillery, is not expected to endorse Webb but is doing everything he can behind the scenes to undercut Good, according to multiple 5th CD insiders on both sides. The offbeat Riggleman was perhaps best known in 2018 for authoring a self-published book about Bigfoot. But he retains a local following, and Webb is counting on defections from his more secular/libertarian supporters.

Good's biggest problem might be money. By the end of June, Good had raised just $259,000 for the cycle, while Webb had raised $1.3 million and is on pace to raise $5 million total for the cycle. Sensing a mismatch — and real danger — the NRCC went on air with coordinated ads in early September to try to bail Good out. The ads warn voters to "look past the smooth presentation" and that Webb would "defund the police."

But Webb perfectly anticipated the attack, immediately responding with an ad accusing Good of "lying" about him wanting to defund the police and then featuring a multi-racial group of beefy retired county sheriffs endorsing his campaign.

The biggest challenge for Webb may be turnout in Charlottesville. Although in-person classes at UVA began on September 8, it's not clear how many students will be on grounds in November and how the pandemic will limit efforts to register them to vote in the 5th CD. The district is extremely polarized, and Webb will likely need at least a 35,000 vote margin out of Charlottesville and surrounding Albemarle County to win.

This wasn't originally a seat Republicans thought they'd have to worry about. But the combination of GOP disunity, an exceptional Democratic candidate and a big fundraising disparity mean they'll need to scramble to avert a disaster. Trump will almost certainly win the district, but private polling taken by both parties suggests Webb's ads have broken through. The race moves from Lean Republican to the Toss Up column.

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