Drake’s legal team is led by Willkie Farr’s Michael Gottlieb, who also happens to be steering Blake Lively’s lawsuit depicting Justin Baldoni as a sexual predator on the set of It Ends With Us. That conflict escalated last week when Baldoni, flanked by his own retinue, countered with a suit that he promised would refute, or at least complicate, some of the accusations Lively lodged on New Year’s Eve. Baldoni’s voluminous 179-page complaint, orchestrated by Bryan Freedman, could give Tolstoy a run for his money with its intricate narrative of allegiances and betrayals, targeting not just Lively, but also her husband, Ryan Reynolds, and publicist Leslie Sloane. The tome frames the dispute not as mere celebrity squabbling, but as “two of the most powerful stars in the world deploying their enormous power to steal an entire film right out of the hands of its director and production studio.” Looking ahead, keep an eye on how each side tries to probe the other’s vulnerabilities for leverage. Consider the claim that Lively and Reynolds meddled with Baldoni’s relationship with WME: This could lead to interesting revelations during discovery, given the talent agency’s conflicting alliances and penchant for oral arrangements with its star clients. There’s also the subplot involving Taylor Swift, one of Lively’s best friends, who has been pulled into the fray for allegedly pressuring Baldoni to include script rewrites by Lively. You can bet that cameo will whet the appetite of the press, as will the accusation that Reynolds lampooned Baldoni in Deadpool & Wolverine—although I have trouble figuring out what’s legally problematic about poking fun at a guy’s self-identification as a feminist. (Perhaps Freedman will argue it violated a non-disparagement agreement, but I’m highly dubious that Reynolds, who wasn’t even party to a deal over the the promotion of It Ends With Us, can’t draw inspiration for a fictional character in another movie.) And surely, Disney and Sony would prefer to steer clear of the drama. Freedman’s latest strategic move—submitting It Ends With Us outtakes to the Central District of TMZ—is bound to raise eyebrows and hints at stratagems to come. (Remember, Baldoni has also filed a $250 million defamation suit against The New York Times for its “We Can Bury Anyone” story, published just before Christmas.) Meanwhile, Baldoni, who was unceremoniously dropped by WME in December, might appear to have little left to lose from a protracted fight. But not so for his co-plaintiff Melissa Nathan, whose high-octane P.R. shop juggles clients including Johnny Depp, Logan Paul, and… Drake. I’m frankly surprised she agreed to be a co-plaintiff in this case, which may subject her high-profile clientele to unwanted exposure. This legal saga may stretch on for years—especially with so many players of all kinds on the stage. Also, don’t overlook the lawsuit against Baldoni, launched by publicist Stephanie Jones, who once represented the filmmaker and then cooperated with Lively’s team when he dropped her for Nathan. This is really a three-way battle.

Late Friday, after a weeklong trial, CNN settled with Zachary Young, the Navy veteran spotlighted in a 2021 exposé on bad actors profiting from aiding Afghans escaping the Taliban. By the time the sides began discussing a deal, a Florida jury had already slapped CNN with a $5 million bill for defamation, teeing up a further round, in which Young’s attorneys gunned for $150 million in punitive damages—a number calculated after considering CNN’s $4.9 million in daily revenue and $2 billion-plus “net worth” (whatever the plaintiff’s economic expert meant by that). Faced with these stakes, CNN cut its losses, promising publicly to mine the ordeal for “useful lessons.” CNN’s loss isn’t a stunner, although many may find it questionable whether the network’s reporters truly branded Young a criminal war profiteer, as he alleged. CNN’s real problem was geographical: The trial was set in Panama City, one of Florida’s deepest-red outposts. Yet what’s truly surprising is how Young’s legal team managed to transform this low-key defamation trial into a referendum on American journalism. In closing arguments, Vel Freedman, Young’s attorney, underlined the presence of reporters in the courtroom and watching the stream remotely, then urged jurors to send a message that would ripple across newsrooms everywhere. “Media companies are waiting by their phones to see what you do,” he told them. As deliberations began, CNN’s Ballard Spahr team drew Judge William Henry’s attention to the Supreme Court’s 2007 decision in Philip Morris USA v. Williams, where a $79.5 million punitive damages verdict was overturned as an unconstitutional violation of due process, since it was based on a jury’s desire to punish the defendant for health damages suffered by cigarette smokers who weren’t involved in the case. Similarly, CNN argued that punitive damages shouldn’t be a vehicle for punishing CNN for the sins of the broader media industry, a nuanced point that the judge was urged to consider. If the parties had not settled, Judge Henry’s interpretation—that while the jury’s punitive damages shouldn’t reflect a general punishment for what the media had done historically, the damages could still act as a deterrent against future journalistic slipperiness—might have ripened into a potent appellate issue. Further complicating matters, Judge Henry was nudged toward the State Farm v. Campbell precedent, suggesting punitive damages shouldn’t dwarf compensatory ones by more than a single-digit multiplier. For all the saber-rattling from the right, framing this as a billion-dollar showdown, and despite Young’s team salivating at the prospect of a $150 million punitive windfall, the initial $5 million compensatory verdict actually offered CNN a lifeline, potentially capping its total exposure at $50 million—a bitter pill, no doubt, but far from a ruinous blow. I bet the settlement hovered around half that—say, $25 million—to sidestep the hazards of an appeal. Some media advocates might balk at the figure, deeming it steep, yet considering the appellate bench is peppered with appointees from Ron DeSantis and Trump, it’s hardly far-fetched. For CNN, it’s a Jake Tapper-sized gulp, the price of shaking off a persistent headache. Late to the game, sure, but as the old adage goes: Better late than never, especially when the lesson is this costly.

Thanks, Eriq. I’ll be back on Thursday evening. Matt