Tired of Winning: Donald Trump and the End of The Grand Old Party

By Jonathan Karl

Dutton, 336 pp.

By Jim Swearingen

For eight years, we have been anticipating a political nadir. After each revelation of Trump and company’s seditious behavior, we think that surely the history cannot get worse. Usually within a day, or a week, it does. Much worse.

Case in point: during a campaign speech at St. Norbert College in Wisconsin in 2016, Donald Trump delivered a telling insight into his approach to leadership: “Always be around unsuccessful people, because everybody will respect you.” That will be crucial to anticipating what the Trump 47 administration will look like as he plots a thoroughly authoritarian regime next time around –- fewer Washington professionals groomed to follow protocol and more unschooled lick-spittles hired to follow orders.

“A team of sycophants” is how ABC News chief Washington correspondent, Jonathan Karl describes them in his new book Tired of Winning. Karl fills in the gobsmacking back story of Trump’s last days in office –- and later out -– as he tried to wheedle and coerce his lieutenants into subverting the presidential election of 2020. Reminiscent of Woodward and Bernstein’s Watergate sequel, The Final Days, Karl’s third in a trilogy of well-researched books on Donald Trump’s seditious behavior reveals new depths of the former President’s laziness, incompetence, and megalomania.

By now, news outlets have saturated the media with Karl’s revelations of presidential malfeasance concerning the election and subsequent insurrection. Not only did the former President falsify public accounts of the election results and unleash a violent mob on the Capitol, but he became fixated on President Biden’s imminent eviction and his own reinstallment in the White House, an electoral scenario entirely missing from the Constitution.

What has garnered less attention in Karl’s post-publication publicity is his reporting of Trump’s attempts to duck the national security apparatus and unilaterally initiate a massive global military retreat just weeks before Biden’s arrival at the White House. Deliberately sidestepping any military or intelligence official who might object, Trump authorized a series of troop withdrawals from Afghanistan first, to be followed with pull-outs from Iraq and Syria, Somalia, Africa at large, and Germany!

The errand boy for this global disarmament, Johnny McEntee, had gone from presidential valet to head of the White House Personnel Office despite a complete lack of political experience, a gambling addiction, and his subsequent firing by chief-of-staff John Kelly. After Kelly’s ouster, McEntee returned to head up a team of loyalty snoops whose job it was to gauge, not credentials or job performance, but fidelity to the administration, including on White House personnel’s social media accounts. Karl likens them to Mao’s Red Guard Youth for their unswerving allegiance to Trump over such things as the United States, the Constitution, and proportional responses to employee’s Instagram Likes.

McEntee’s primary job was to keep the boss happy, delivering whatever hair-brained scheme Trump might order. He was tasked with implementing the slap-dash, lame-duck plan to remove troops from commitments around the globe while dodging the responsible national security brass at crucial levels. McEntee drafted a Presidential Order using previous orders and an internet search of such documents as templates. The incoherent, cribbed directive triggered Joint Chiefs Chairman, Mark Milley, into backtracking the order all the way to the President. Trump folded on the plan once he discovered how much work navigating the national security bureaucracy actually entails.

The underlying blessing in all of Trump’s sedition is that he lacked the discipline to learn how the Executive works and apply himself assiduously to matters of state. His ability to accomplish various treasons next time will hinge on having a loyal, but larger team of Johnny McEntees to ignore the “deep state” apparatus that forestalls a dictatorship. Karl makes the disturbing observation that having narrowly averted an authoritarian regime the last time around, the guardrails of our democracy are now gone on the Republican side. There will be no milquetoast patriot like Sessions, or Barr, or Pence to utter a timid "No" next time.

Karl concludes the book with a deeply patriotic homage to the Capitol and the Congress–both nearly destroyed on 9/11 and on January 6th. He frames the defenders of the institution through John Kennedy’s book Profiles in Courage, nominating a couple dozen heroes, Republicans all, for sacrificing the remainder of their professional careers to stymie Trump's treachery. Karl honors them for taking that road. So should we all.

Jim Swearingen is a Minneapolis-based writer.