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President Trump鈥檚 鈥渃ovfefe鈥� moment says it all.

Early Wednesday, the president had tweeted what appeared to be an incomplete thought, ending with a nonsense word: 鈥淒espite the constant negative press covfefe.鈥�

After his apparent mistake sent the political universe into a day of jokes, Trump turned it into another 鈥渓ook at me" moment, tweeting: 鈥淲ho can figure out the true meaning of 鈥榗ovfefe鈥� ??? Enjoy!鈥�

At a time of turmoil at 1600 Pennsylvania Avenue 鈥� with a press secretary appearing grim-faced and stressed and a communications director having tendered his resignation 鈥� 鈥渃ovfefe鈥� showed who鈥檚 really in charge of White House communications: Trump himself. His messaging staff is just riding in the chase car.

鈥淯ltimately, the best messenger is the president himself,鈥� White House spokesman Sean Spicer said Tuesday (pre-covfefe).

That suggests a Herculean assignment for those tasked with speaking for the president. Even in the best of times, White House communications is a high-wire act, with scores of aides working to advance the president鈥檚 agenda, keep the team 鈥渙n message,鈥� and wrangle an unruly press corps.

When a major investigation involving a special counsel enters the picture 鈥� see presidents Nixon, Reagan, Clinton, and now Trump 鈥� a new kind of communications strategy is called for: one that walls off questions about investigations from the routine issues of the day.

With Trump, the challenges increase exponentially. He is new to governing, and doesn鈥檛 have that muscle memory to fall back on when major distractions encroach. He is understaffed, both in his communications team and throughout his administration. And he is prone to going off-message and undermining his spokespeople, both in media interviews and on Twitter.

News reports have pointed to White House challenges in finding good people willing to fulfill key roles, but there鈥檚 another issue: The Trumpian culture is to keep the team small. He ran both his businesses and his presidential campaign that way. In government writ large, holding back on hiring has also furthered the Trumpian goal of 鈥渄econstructing the administrative state.鈥�

Then there are the multiple Russia investigations, a story of international intrigue that brings near-daily developments.

鈥淚t鈥檚 an elaborate running story and every day it builds on itself, everyone finds a new person, a new angle, a new investigation, a new leak,鈥� says Stephen Hess, who advised former presidents Dwight D. Eisenhower, Richard Nixon, Gerald Ford, and Jimmy Carter, and is a scholar on governance at the Brookings Institution. 鈥淭hese folks don鈥檛 really know how to stop the leaks.鈥�

Mr. Spicer has probably suffered more public humiliation than any White House press secretary in history, from Melissa McCarthy's parodies of him on "Saturday Night Live" to slights at the hands of Trump himself.听

Republicans, not surprisingly, have sympathy for Mr. Spicer.

鈥淚 don鈥檛 think that you need to fire Sean Spicer,鈥� says Republican strategist Ford O鈥機onnell. 鈥淵ou need to enlarge the comms shop. Find talent who can come in and are loyal.鈥�

鈥淭he news is just moving faster than ever,鈥� says Mr. O鈥機onnell. 鈥淎nd you have a boss who likes to change subjects in a heartbeat. This is a very, very hard job, no matter who you are. But there still needs to be more strategic planning, because the better the strategic planning, the better the execution.鈥�

Even Mike McCurry, one of former President Bill Clinton鈥檚 press secretaries, offers a bit of succor for the incumbent.

鈥淭he poor guy hasn鈥檛 had many breaks,鈥� says Mr. McCurry, now a professor of public theology at Wesley Theological Seminary in Washington. 鈥淎nd it鈥檚 impossible if you have only an audience of one that counts.鈥�

McCurry also offers sympathy for Trump鈥檚 decision not to bring along Spicer, a devout Roman Catholic, when he met the pope, says McCurry. 鈥淚 felt sorry for that. There are very few perks with all the hardship that goes with the job. But you deserve a few of those.鈥�

'You can't go to war with the press'

Speaking more broadly about the job of White House press secretary, McCurry lays out the basic challenge: serving both the president and the press corps.

鈥淵ou will rarely keep both sides of that equation happy, but you鈥檝e got to have the trust and confidence in both sides of that adversarial relationship in order to make the job work,鈥� he says. 鈥淚f it gets out of balance, you鈥檙e probably not going to be successful.鈥�

McCurry is widely seen as being among the best to have held the job 鈥� even as he navigated the Monica Lewinsky scandal. His formula involved creative deflection and a quick wit.

鈥淭elling the truth, slowly鈥� is one of his better-known explanations for how he avoided lying.

鈥淢y general rule was, you have to keep people aimed toward the truth and you can鈥檛 deliberately deceive,鈥� he says. 鈥淏ut sometimes you have to be artful in the way in which you provide information.鈥�

McCurry doesn鈥檛 want to comment on the current White House, but he does offer this general advice: 鈥淵ou can鈥檛 belligerently go to war with the press. It鈥檚 an adversarial relationship, but it only works if it鈥檚 an amicable adversarial relationship.鈥�

Spicer 鈥� attacked and attacking听

Spicer has had a longstanding relationship with Washington media, going back to his days as a strategist and spokesman for the Republican National Committee and before that, handling communications for the House Republican Conference and public affairs for the US trade representative.

Taking on both the communications and press secretary jobs for Trump has no doubt been the challenge of a lifetime. Trump鈥檚 original choice for communications director, Jason Miller, resigned before Inauguration Day over a personal matter, and Spicer did the job until Mike Dubke came in on March 6.

Mr. Dubke stayed largely behind the scenes, and on May 18 offered his resignation. Besides Spicer and his principal deputy, Sarah Huckabee Sanders, senior Trump advisers and Cabinet secretaries have taken turns speaking for the boss on television, and in briefings.

After five weeks in office, Trump gave himself a middling grade 鈥� 鈥渁 C or a C+鈥� 鈥� for messaging, even as he awarded himself an A for 鈥渨hat I鈥檝e actually done鈥� and an A+ for effort.

That assessment was seen as a slam on his staff, especially his communications team, and rumors of Spicer鈥檚 imminent firing or resignation have become routine. Other reports show Spicer moving to a more behind-the-scenes role while Ms. Sanders would do more on-camera work.

On Tuesday, when Spicer was asked whether Trump was happy with White House messaging, his answer was 鈥測es, but鈥� 鈥� and turned the question into an attack on the media.

鈥淚 think he's very pleased with the work of his staff,鈥� Spicer said. 鈥淚 think that he is frustrated, like I am and like so many others, to see stories come out that are patently false; to see narratives that are wrong; to see quote-unquote, 鈥榝ake news.鈥� 鈥�

When asked for an example, he named an erroneous report about Trump not listening to the simultaneous interpretation during the recent G7 summit in Italy. (When the truth came out, that story was corrected.)

Spicer then ended the briefing abruptly. The next day, he appeared before the press, off camera, for just 12 minutes.

How humor can help

Gone are the days when Trump could pose as his own publicist 鈥� as he did in the 1990s, calling reporters as 鈥淛ohn Miller鈥� or 鈥淛ohn Barron鈥� to discuss his personal life and business prowess.

Now Trump is consumed by the business of the presidency, and even if Spicer thinks Trump is his own best messenger, that鈥檚 not realistic on a daily basis. Suggestions that Trump might do away with daily briefings by a spokesperson, and hold a press conference himself every two weeks are also unrealistic, say experts on media-White House relations.

Every day, most questions from the press are predictable, and more efficiently handled in a group setting rather than in individual contacts between the press office and reporters.

Peter Fenn, a veteran Democratic communications strategist, blames Trump for the problems with his press shop.

鈥淭his White House communications operation is not organized, is not disciplined, and is not rational,鈥� Mr. Fenn says. 鈥淎nd it starts at the top.鈥�

McCurry credits humor with getting him through his toughest moments as Clinton鈥檚 press secretary.

鈥淲hen I got stuck, humor was the only thing left in your toolbag,鈥� he says. 鈥淥ne time, after the 80th straight question on Monica Lewinsky, I used a line someone else gave me. I said, 鈥楲ook guys, you鈥檝e got me double-parked in the no-comment zone.鈥� 鈥�

鈥淓verybody laughed. Then we moved on to the next subject. If you don鈥檛 have the ability to laugh at the absurdity of it all, then it鈥檚 going to be very grim.鈥�