Left-leaning political commentator Keith Olbermann is openly celebrating what he now calls a lucky escape from his past relationship with disgraced former New York Magazine reporter Olivia Nuzzi, whose personal life and professional downfall continue to generate headlines.

The former MSNBC host resurfaced online after social media users pointed out that he had once dated Nuzzi more than a decade ago — at a time when she was just 21 years old and he was 55. Instead of addressing the age-gap controversy directly, Olbermann appeared far more interested in commenting on a new wave of allegations swirling around his ex.

Olbermann mocks Nuzzi’s “tangled” romantic past

After journalist Ryan Lizza — Nuzzi’s former fiancé — publicly claimed that Nuzzi had a romantic relationship with former South Carolina Governor Mark Sanford while covering him in 2020, Olbermann jumped at the opportunity to weigh in.

“Ryan Lizza appears to be accusing Olivia Nuzzi of an affair with Mark Sanford when she was covering HIM in 2020?”
Olbermann posted on X.

Moments later, he followed it up with a meme of Keanu Reeves in The Matrix dodging bullets, captioning it:

“This is me.”

The implication was clear: Olbermann believes he narrowly avoided deeper involvement in Nuzzi’s personal and professional implosions.

Olivia Nuzzi with her then-fiancé Ryan Lizza.

Lizza’s allegations paint a very different picture of Olbermann

While Olbermann made light of the situation, Lizza’s claims painted a more troubling portrait of their former relationship. According to Lizza, Olbermann acted as a “sugar daddy”, allegedly paying for Nuzzi’s:

• college tuition

• designer Tom Ford and Hervé Léger dresses

• and $15,000 worth of Cartier jewelry

Lizza suggested that although Olbermann was generous, “there were strings attached.” He said Nuzzi hid the relationship from him and others, but eventually revealed it in full detail.

“One day she told me everything — too much, actually — and together we hatched a plan for her escape,”
Lizza claimed.

Olbermann, for his part, completely sidestepped these accusations in his online commentary, focusing instead on Nuzzi’s connections to Sanford and the scandal dominating the political news cycle.

Keith Olbermann tweets he dodged a bullet after excerpts of Olivia Nuzzi’s memoir were released.

Nuzzi’s RFK Jr. sexting scandal continues to spiral

Nuzzi has been under intense scrutiny ever since revelations surfaced about her sexually explicit communications with Robert F. Kennedy Jr. during his presidential campaign. The affair ignited a media firestorm, ultimately derailing her career and ending her engagement to Lizza.

Her upcoming memoir — which reportedly contains intimate details of the RFK Jr. scandal — has only escalated public interest. Lizza published his own account within hours of excerpts from the book leaking, posting a newsletter titled “Part 1: How I Found Out.”

A saga of scandal, schisms, and scorched-earth revelations

In just a few days, the intertwined personal histories of Nuzzi, Olbermann, Lizza, and RFK Jr. have resurfaced in dramatic fashion. The public has now been offered:

• Olbermann’s gloating social-media commentary

• Lizza’s blistering personal exposé

• Nuzzi’s forthcoming tell-all memoir

All of it together paints a picture of a journalist whose rise was meteoric — and whose fall has only intensified as former partners and colleagues speak out.

For now, Olbermann appears content to portray himself as the one who “dodged a bullet.” Whether he continues to avoid deeper scrutiny regarding his own past with Nuzzi remains to be seen.