Update, 9:30 p.m: Vasquez beat O'Connor 54 to 46.

Ald. Patrick O'Connor has been on the City Council for 36 years. In that time, you'd think he'd have racked up plenty of accomplishments to brag about: schools, libraries, parks.

But as O'Connor, Chicago's second-longest serving alderman, faces the first runoff of his career, he's campaigning on a single issue: all the nasty stuff his opponent, 39-year-old Andre Vasquez, said during his career as a battle rapper.

I'm a resident of O'Connor's 40th Ward. Almost every day, I receive another slick mailer detailing hateful comments Vasquez made in rap songs and on online message boards in the 2000s.

First came "Guess Who Made That Comment, Starring Andre Vasquez" illustrated with a photo of a game show host in a plaid blazer. "Who Made This Nasty Comment?" the flip side asks, before listing all sorts of unprintable statements made by Vasquez, which, at their worst, imagine violence against women and gay people.

This was followed by a mailer comparing Vasquez to Ike Turner, whose abuse of wife Tina Turner was detailed in her autobiography, What's Love Got to Do With It? It featured a photograph of a woman with a black eye.

Finally came a gatefold with a photo of Donald Trump on the cover, alongside another offensive message board post. "Donald Trump did NOT say [this]," it read. "But if he did, we'd be outraged." Inside was a photo of Trump in a red MAGA cap, facing a photo of Vasquez in a Philadelphia Phillies cap, which is … also red.

For people who recycle their junk mail, O'Connor has a website, www.thetruthaboutandre.com.

Vasquez has apologized for the comments, telling the Sun-Times:

“I just didn’t have, really, the education and context. Because I felt inadequate in my own skin, I denigrated others. There aren’t any excuses for it. I unequivocally apologize for that. But that’s not the person I am. It’s not the person who, prior to being part of the campaign, was organizing in the city.”

Nonetheless, O'Connor keeps bringing up the lyrics and message board posts. During a debate at Amundsen High School, Vasquez finally fired back by invoking a regrettable episode from O'Connor's own youth: in 1983, as a 28-year-old freshman alderman, O'Connor aligned with the Vrdolyak 29, the bloc of white alderman who united to thwart Mayor Harold Washington's legislation and appointments.

"I wonder what the Vrdolyak 29's social media would have looked like," Vasquez said.

It probably would not have been racially enlightened. But O'Connor likely made his most egregious errors before the invention of the internet, which is turning out to be a rich source of oppo material on Millennial politicians. In the 5th Ward, 30-year-old challenger William Calloway has had to answer for calling gay marriage "an abominable sin" after the Supreme Court declared it legal in all states.

Today, young people conduct much of their social lives online. The obnoxious comments that past generations made in person, or over the phone, now linger forever. Vasquez is a member of the Democratic Socialists of America and a son of Guatemalan immigrants, but he's given O'Connor the tools to portray him as a mini-Trump to the LGBTQ+ community in Andersonville.

It doesn't seem to be working. O'Connor won only 33 percent of the vote in the primary. That's pitiful for a veteran alderman, and helps explain why he's running such a desperate, nasty runoff campaign. Meanwhile, Vasquez conducted an internal poll that shows him leading O'Connor 53 percent to 38 percent in today's election.

Still, be careful what you type on the internet, folks. I'm getting tired of all this mail.