Two media veterans, Oprah Winfrey and Gawker Media’s Deadspin, had the chance to hit online advertising gold this week as record numbers of people came to their websites for tales of tarnished athletes. They came up short, however, and showed — again — how the ad industry is not ready for big moments on the web.

In the case of Oprah, her flub came Thursday night when she aired the confessions of disgraced cyclist Lance Armstrong. The interview was broadcast on her OWN cable network but also on the OWN website where blank silence filled the spaces where ads should have been. Media experts took to Twitter in surprise:

Remind me again: why are they not showing ads in the OWN online livestream? God forbid people watch ads for once?

— Rafat Ali (@rafat) January 18, 2013

kind of concerned, it wasn’t just one pod – it’s all the “commercial” breaks. dead air. OWNTV online needs sales help.ownspecial.oprah.com/lancearmstrong…

— Lora Kolodny (@lorakolodny) January 18, 2013

New York Times reporter Brian Stelter suggested the absence of ads could be tied to technical or licensing issues, while paidContent founder Rafat Ali concluded the reason was simply “incompetence.” Whatever the reason, it does appear that Oprah and her struggling OWNTV brand left a big pile of money on the table by playing a major scoop without ads. OWNTV did not respond to a request for comment.

Sports site Deadspin also experienced ad issues this week after it broke the mind-boggling story about how football star Manti T’eo’s dead girlfriend — a beautiful Stanford co-ed with “the warm smile and soulful eyes” — was a creature of fiction. As Ad Age reports, the story attracted a record-breaking 3.5 million visitors Thursday night but Deadspin’s parent company, Gawker Media, didn’t have the ad inventory to capitalize on the flood of traffic. The missed opportunity is leading Gawker Media to explore technical solutions, such as a private exchange that lets advertisers bid in real time, for the next time it has a massive story like T’eo or explicit (NSFW) Brett Favre photos.

Internet scoops have been around for a decade, so why are publishers still having such a hard time figuring out the ad equation? Part of it is indeed technical. A massive traffic surge means publishers must match buyers and sellers on very short notice — although, in the case of both Oprah and Deadspin, the nature of the story meant the sites likely had weeks to prepare.

The technical side is one part of the explanation. Another relates to the nature of major news stories which often involve sordid or awful events, creating a risk for both publishers and advertisers — see the bloody t-shirt ad Fox ran during the Newtown shooting. Stephen Roy, a longtime ad man at Edelman who now works for Disqus, explained the situation well in an email to paidContent: