concept: maggie works long hours filling out paperwork for her cases, and she ends up staying at the office until well into the night. kara also stays out late sometimes, flying around the city to keep watch when she can’t sleep. since maggie and alex started dating, kara makes sure she flies by maggie’s office just to check on her. whenever she sees maggie there working in the middle of the night, she always drops by with coffee. at first maggie is so shocked that she almost chokes on the lump in her throat, and kara is fiddling with her glasses saying, “oh, it’s nothing.” but then it becomes a sort of routine, and they grow closer and more comfortable with each other because of it. but some nights kara can’t make it because she’s out on supergirl duty, so she sends james. he walks in like, “kara is busy but she wanted to make sure you got your coffee tonight,” and sits with a stunned maggie for awhile while she works. and then one night winn shows up with coffee AND donuts because how can you have one without the other? the three of them start rotating who goes on what night, and maggie can’t believe it. she even starts to look forward to her late nights because she knows one of them will show up to keep her company. all that time she’d spent worrying about them accepting her after she started dating alex, and all it really took was little danvers, and a simple cup of coffee.
Short Answer: No, mostly because I don’t think it is conscious on his part.
The issue with the West Wing (especially the Sorkin era) is that it’s mainly written by Sorkin himself. While that leads to amazing speeches and a wonderfully written show. It also leads to there being a very singular view of issues. Which is also the reason why that part of the show is more like a political fairy tale than anything else. It is what Sorkin wants politics to look like.
One main issue that was out of his control, is that you need someone for exposition. People who work in the White House know what they are doing (at least until recently). They are highly trained operatives and are experts in policy. In other words, they know way more than the average viewer. So these concepts need to be boiled down to for the viewers. Which is were Donna comes in. She is the conduit for the viewer. Through her questions Josh gets to explain to the audience what’s going on. This makes her look dumb because real White House assistants know at least the basics about the policy their bosses are working on. It also doesn’t help that there isn’t a single male assistant in the show, and that there is only one female senior staffer (CJ). Who almost always needs schooling on the finer policy points, even after years of working in politics. Again some of this changes when she becomes Chief of Staff and Donna moves out, but it’s always there.
Another thing is that the show ended more than a decade ago (I know crazy). Things were a lot different then, character like Ross Geller (the nice guy) were at the height of their power. As I have said before people learn and change. I for one think that The Newsroom is a step up for Sorkin. While the whole Jim mansplaining to Maggie thing is annoying, but is also a conduit for the audience. Sloan and MacKenzie is constantly putting men through their paces (see Sloan’s interview with website asshole).
The fact that winn says ‘I am very excited to meet alex’s new mystery man’ means alex definitely mentioned this to the gang earlier which shows she’s probably been waiting to introduce maggie for a while now and was waiting for the right time. Also I am actually really happy the writers made winn and james say male pronouns 'what does HE do for a living’ because it completely shows how heteronormative people can be without even knowing and it’s almost quite smug when maggie walks up to them all 'surprise bitch’ looking.