On Monday morning, Sen. Kyrsten Sinema joined Sen. Mitch McConnell to chat about bi stuff — in this case, a speech called “The Future of Political Discourse and the Importance of Bipartisanship.” Sinema gave the talk at the University of Louisville’s McConnell Center, where the institution’s eponymous ally described Sinema as the “the most effective first-term senator I’ve seen in my time in the Senate.”
It’s no shock that the Senate minority leader and the Arizona Democrat are cozy; Sinema’s greatest joys have included safeguarding the 60-vote threshold known as the filibuster and torpedoing her own party’s first-term agenda. But this latest chummy interaction did yield at least one surprise: a divulgence from longtime MSNBC personality Keith Olbermann, who claimed on Twitter that he dated the Arizona Senator for an unspecified length of time between 2010 and 2011 — and that Sinema, during that period, was a “legit progressive.”
Olbermann’s public rapport with Sinema goes back to the 2012 elections, when he claims he gave the senator her first national TV appearance. Sinema was running for the House of Representatives, and Olbermann brought her onto his MSNBC show on at least two occasions in that campaign cycle. If Olbermann’s stated timing is accurate, then both of those conversations had to have taken place when or after they supposedly dated, though the pundit did not mention it in either interview.
Since then, Olbermann has made occasional statements in support of Sinema’s political ambitions, tweeting once in 2017, “Sinema 2020.” But when that election did roll around, whatever goodwill that remained between them appears to have evaporated. Olbermann has even, on several occasions, criticized the senator by referencing their prior social relationship. In July 2021, he called them “ex-friends.” In January, he tweeted: “I say this as her former friend and the person who first gave her national television exposure on @msnbc: @SenatorSinema needs to resign or be removed from office immediately.”
But in early August, Olbermann started using different language to describe their ex-friendship — a change which happened to coincide with the premiere of his new podcast, Countdown. On Aug. 1, he tweeted a link to the show’s premiere episode, promising intel on “all the news and sports, memories of Bill Russell. And btw my dates with Krysten Sinema” (emphasis added). Three days after that, he hinted at it again:
This poses some questions. Namely, how and in what context did these two interact, roughly 11 to 12 years ago? Were they seeing each other when Olbermann made two donations to Arizona Democratic Representatives before the 2010 elections, which resulted in him getting suspended without pay from his show for an indefinite period that wound up being two weeks? What evidence that Sinema was a “legit progressive” did he see? Was she still driving her 1997 Nissan Maxima SE at the time? Has she always dressed that way? (Apparently, yes.)
We reached out to Olbermann and Sinema’s representatives for comment. We have not heard back yet, but we will update if they do. If you have any other information, drop us a line at email@example.com.