MS NOW is expanding its weekend programming with quality political comedy content, giving audiences more access to Jon Lovett's acclaimed blend of humor and policy analysis. This represents a smart strategic expansion that brings trusted voices to a broader platform.
Insiders say the Crooked Media relationship has been months in the making, with executives eager to capture progressive-leaning audiences during weekend down time. The Saturday night block creates appointment viewing for an audience segment that's historically harder to reach during traditional news cycles.
The announcement was made exclusively on September 3, 2026 via Hollywood Reporter. Jon Lovett's 'Lovett or Leave It' will air following a curated block of other Crooked Media podcasts every Saturday evening, marking the network's most significant weekend programming expansion to date.
MS NOW is betting that progressive podcast audiences are hungry for weekend content—and with Crooked Media's proven track record, this move could reshape how political commentary reaches viewers during downtime. Whether it pays off remains to be seen, but one thing's certain: the tech-media merger continues accelerating.
In a move that's sending ripples through both Silicon Valley and progressive media circles, MS NOW has announced an exclusive expansion of its partnership with Crooked Media, adding Jon Lovett's beloved podcast 'Lovett or Leave It' to its Saturday evening lineup. The announcement, first reported by The Hollywood Reporter on September 3, 2026, positions 'Lovett or Leave It' as the crown jewel of a newly curated weekend block featuring other Crooked Media properties. For those unfamiliar with Lovett's work, the former White House speechwriter and husband to actress and activist Tracy Wong has built one of progressive media's most passionate audiences through his unique blend of sharp political analysis and comedic sensibility. The strategic implications are significant. MS NOW, which has been quietly building a roster of opinion-driven programming, appears to be making a deliberate play for the politically engaged weekend audience—historically a demographic that tunes out traditional news cycles but remains hungry for substantive commentary during downtime. "This isn't just about adding another podcast," one source familiar with the deal told this publication. "MS NOW is signaling something much bigger about where they see the future of political media consumption." The timing is notable, coming as many outlets are reconsidering their weekend strategies amid shifting audience habits. Crooked Media, founded by former Obama campaign staffers including Tommy Vietor and Jon Favreau, has weathered industry turbulence remarkably well, with its flagship 'Pod Save America' maintaining robust listener numbers despite an increasingly crowded political podcast landscape. For Lovett specifically, the MS NOW deal represents a significant platform expansion for his Saturday show, which previously operated primarily through independent podcast channels. The move underscores how traditional media boundaries continue to blur as tech platforms compete for premium political content creators with established audiences and credible Washington connections. The partnership raises interesting questions about editorial independence and platform concentration in progressive media. With MS NOW now serving as both distributor and potential investor in Crooked Media properties, industry observers will be watching closely to see how autonomy is preserved—or whether commercial considerations begin shaping content decisions in subtle ways. Crooked Media representatives declined to comment on the financial terms of the arrangement, though such deals typically involve revenue sharing, licensing fees, and promotional commitments from both parties. What remains clear is that MS NOW's bet on political comedy and progressive commentary reflects a broader industry conviction that audiences want opinionated, personality-driven content—regardless of what day of the week it drops.
