Season 1, Episodes 5-7: "Mary Pat Shelby," "The Head Coach, Dinner and The Morning Mail," "Dear Louise..."
As far as Internet truisms go, "Aaron Sorkin can't write women," is right up there with "Never start a land war in Asia."
I haven't always understood this criticism; I see it more clearly on the fringes of his work. You can tell Sorkin wants to write powerful, independent women with strengths and foibles and motivations. He has an idea of what they’re supposed to look like. It's just that a lot of times, the traits he's trying to imbue get lost in translation. At worst, this results in the caricaturish Lt. Cdr. JoAnn Galloway in A Few Good Men, who comes across as shrill and over-matched at nearly every turn (at least based on Demi Moore's portrayal in the film version; I’ve never seen any stage productions). On the other hand, Annette Bening’s formidable lobbyist-cum-presidential-paramour in The American President is well-rounded and engaging, with entirely believable moments of strength and weakness. (Of course, it’s fair to ask how much of the disparity here is due to the relative acting talents of Moore and Bening.)
Sports Night makes a conscious effort to present two female characters in positions of authority. As, respectively, the producer and senior associate producer of Sports Night, Dana Whitaker and Natalie Hurley are drawn as smart, successful women in the traditionally male-centric world of sports journalism. The challenges faced by women in this particular profession (no less today than in 1998, sadly) are arguably greater than in any other consumer industry. Those challenges form the wellspring of the main story in "Mary Pat Shelby," a story which continues - and is disappointingly squandered - in "The Head Coach, Dinner and The Morning Mail."