This post has been updated to include Allen's 2009 story on "salons" planned by The Washington Post.

We've known for a while that Mike Allen is leaving Politico after the presidential election, along with chief executive Jim VandeHei and chief revenue officer Roy Schwartz, to start a new venture. But now we know Allen will end his run as Playbook author sooner than that. Anna Palmer and Jake Sherman will take over the morning tipsheet on July 11 with continued help from Allen assistant Daniel Lippman.

With Allen setting a date for his torch-passing, now is a good time to remember some of the moments that have helped define Playbook. These aren't necessarily the most important moments in Playbook history, but they capture the distinct characteristics that have made it a must-read and much-talked-about for the last 3,285 days.

The launch

The first edition of Playbook, published June 25, 2007, stated the newsletter's mission: "Welcome to the new edition of the Politico Playbook that's available by automatic e-mail, giving you a handy, BlackBerry and Treo-friendly peek at the news driving each day."

The BlackBerry and Treo references seem pretty antiquated today, but the vision of a mobile-friendly news digest was clear from the start.

How many houses does John McCain own?

Playbook is primarily a roundup of other journalists' reporting, but the well-connected Allen sprinkles in original scoops — sometimes so casually that he could be accused of burying the lead. A prime example appeared in paragraph 17 of the Aug. 21, 2008, edition, where Allen ended his summary of an interview he and then-colleague Jonathan Martin (now at the New York Times) conducted with that year's Republican presidential nominee, John McCain.

"McCain said he would have the staff get back to us on how many houses he and his wife, Cindy, owned," Allen wrote. "David Axelrod recently told Adam Nagourney it was seven, an estimate that Newsweek had used this summer for all of the McCains' real-estate holdings."

Allen and Martin also wrote a separate article about McCain's uncertainty, which quickly blew up into a widely covered story about how the Arizona senator seemed out of touch — so wealthy that he couldn't even keep track of his many homes.

Keeping an eye on the competition

Media gossip is a Playbook specialty, and Allen shared a juicy bit in July 2009 when he got his hands on a flier advertising an off-the-record, "collegial evening with Obama administration officials, Congress members, business leaders, advocacy leaders and other select minds" — including reporters — at the home of The Washington Post's then-publisher, Katharine Weymouth. The "salon" was conceived as the first in a series of 11, and companies could pay $25,000 (or $250,000 for all 11) for their executives to participate.

Weymouth was quoted in the Post the next day, saying, "the fliers got out and weren't vetted. They didn't represent at all what we were attempting to do. We're not going to do any dinners that would impugn the integrity of the newsroom." A marketing executive took the blame for approving the fliers without running them by the newsroom.

When Weymouth left the newspaper in 2014, she remarked to Ellen McCarthy that she is sure the salon episode is destined to appear in her obituary.

'The man the White House wakes up to'

Less than three years into his Playbook-ing, Allen was already required reading at 1600 Pennsylvania Ave., according to a 2010 New York Times Magazine profile. The Times story described "friend-sources" as "the dominant hybrid around Mikey," pointing out the blurry line that has elevated Allen to ultimate insider status and also made him a target of criticism, on occasion.

The lead of the Times piece highlighted Allen's rapport with aides to President Obama:

Before he goes to sleep, between 11 and midnight, Dan Pfeiffer, the White House communications director, typically checks in by e-mail with the same reporter: Mike Allen of Politico, who is also the first reporter Pfeiffer corresponds with after he wakes up at 4:20. ...
Like many in Washington, Pfeiffer describes Allen with some variation on "the most powerful" or "important" journalist in the capital. The two men exchange e-mail messages about six or eight times a day. Allen also communes a lot with Rahm Emanuel, the White House chief of staff; Robert Gibbs, the press secretary; David Axelrod, President Obama’s senior adviser; and about two dozen other White House officials. But Pfeiffer is likely Allen's main point of contact, the one who most often helps him arrive at a "West Wing Mindmeld," as Playbook calls it, which is essentially a pro-Obama take on that day’s news. (Allen gets a similar fill from Republicans, which he also disseminates in Playbook.)

The no-surprises interview offer

Allen's coziness with certain sources caused him some embarrassment in November, when Gawker published a 2013 email exchange between him and Philippe Reines, an aide to then-Secretary of State Hillary Clinton. Allen wanted to interview Clinton's daughter, Chelsea, at a brunch event put on by Politico.

"No one besides me would ask her a question, and you and I would agree on them precisely in advance," Allen wrote. He added that "The interview would be 'no surprises.' I would work with you on topics and would start with anything she wants to cover or make news on. Quicker than a network hit and reaching an audience you care about with no risk."

Allen responded to the Gawker story in Playbook, writing that his email to Reines "makes me cringe." He said Politico has a policy against sharing questions in advance and that he "should never have suggested we would."

Gawker also reported in February that, on another occasion, Allen allowed Reines to ghostwrite a Playbook item.

Rahm goes Rahm-bo over private conversation

An interview with Emanuel, now the mayor of Chicago, at a Playbook event in December turned super-awkward when Allen asked about Emanuel's upcoming family trip to Cuba. It was a question most journalists wouldn't have known to ask, since Emanuel had not publicized his travel plans, and it had the potential to elicit an interesting, insightful answer — precisely the kind of nugget Playbook is known for.

In the end, it did. Emanuel recalled previous trips to India, Zambia, Vietnam, Laos and other countries, saying his children "get to be exposed to other cultures, other parts of the world." But first he ripped into Allen.

"Thanks for telling everybody what I'm gonna do with my family," Emanuel said. "I really — you just had a private conversation with me, and now you decided to make that public. I really don't appreciate that."

The episode typified the delicate balance Allen has sought to strike. His relationships with newsmakers can yield scoops and anecdotes that readers love, but confusion about what is and is not on the record has the potential to fray those very same relationships.

Native advertising pioneer

Playbook ads aren't exactly eye-catching. But that's kind of the point. They appear as plain text among the news of the day, increasing the likelihood that skimmers will consume their messages before realizing they are actually commercials.

Playbook has used this camouflage style for eight years now — occasionally at first, but now daily. Allen started well before native advertising became all the rage in the media business. The Erik Wemple Blog recognized him as a native advertising pioneer in 2013. But the lines between what is an ad and what is editorial were sometimes blurry, as Wemple also reported:

The distinctions between Mike Allen/”Playbook” and the rest of Politico say a great deal about one of the most talked-about American media properties of the past decade. Whether by design or default, “Playbook” has become the place where Politico gives long hugs to powerful Washington interests, including advertisers. Elsewhere in the publication, straight-up reporting prevails.
While Allen sees himself as one of Washington’s top journalists and recently departed CEO Frederick J. Ryan Jr., sees him as the modern-day incarnation of Edward R. Murrow and Walter Cronkite, other Politico reporters don’t practice his style of journalism. They dig for documents and publish stories that offend power. Along the way, they may even cover for their sources, though not in the manner of Mike Allen.
Politico’s leaders didn’t cooperate for this piece. In rejecting a sit-down discussion, Editor-in-Chief John Harris said the premise “is without merit in any shape or form.” Without an interview, it’s impossible to judge Allen’s motivations. For example, does he write nice things about the chamber because he wants more advertisers or because he feels their agenda doesn’t get fair play in other outlets? Did he publish those BP plugs because he thought they were newsworthy or because he’s got a friend at the company?
Whatever the explanation, the core softness in “Playbook” and Allen’s news stories counters the public image that Politico’s leadership has promoted for years. This news outlet, former Executive Editor Jim VandeHei and others have preached, is a take-no-prisoners operation, forever fighting off complacency and doing gritty work. At the same time, its most famous reporter is dropping puffballs across the Internet. As VandeHeiwrote upon being elevated as chief executive officer of Politico, “We are successful because our business and editorial strategies work in perfect synchronicity.”
A precise, and perhaps accidental, description of “Playbook.”

It's still unclear what Allen is planning post-Politico, but his business savvy should serve him well in his next venture.