President-elect Joe Biden and his Democratic allies will probably spend the first several weeks of Biden’s administration fighting with congressional Republicans over the size of a COVID-19 relief package. That legislative battle could delay, by weeks or even months, critical aid for millions of Americans who are suffering financially because of the COVID-19 pandemic.

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That was one of the many insights provided by Politico senior writer and best-selling author Jake Sherman, a Cleveland Park resident who spoke during a Tuesday Talk webinar on Nov. 17, the last Tuesday Talk of 2020.

“COVID relief is going be a massive, massive legislative battle,” predicted Sherman, a regular contributor to NBC News and the co-author of Playbook, Politico’s franchise newsletter, which comes out twice a day. 

The two sides, Sherman said, “are just in completely different positions.”

Republicans want a relatively, small targeted COVID relief package of $500 billion with little money for state and local governments. Democrats, by contrast, seek a $2 trillion package that includes dramatic increases in unemployment insurance and significant funds for state and local governments.

Republicans, seeing an improving job market and a COVID-19 vaccine, do not think it is necessary to pump trillions into the economy, creating an impasse between Republicans and Democrats that could last beyond the first quarter of next year.

“I am pretty bearish about a COVID relief bill being quick or easy,” commented Sherman, co-author of the national best seller, The Hill to Die On: The Battle for Congress and the Future of Trump’s America, published in April of 2019.

Sherman also expects Biden to try to enact legislation to improve and expand the Affordable Care Act, a signature issue for the Democrats. But passage of a health care bill will be a difficult task with a Republican-controlled Senate. 

Future control of the Senate hinges on two elections in Georgia. Georgia will hold run-off elections for two Senate seats in early January, and Democrats will have to win both seats to achieve a 50-50 draw in the Senate – ties that can be broken by the vote of the Vice President — in this case, Vice President-elect Kamala Harris.

Like most analysts, Sherman does not expect the Democrats to capture both Senate seats, leaving the Senate in control of the Republicans. By controlling the Senate, Republicans will be able to block the Biden administration’s legislative initiatives for the next two years and possibly longer depending on the outcome of the 2022 mid-term elections.

“Republicans had to pull an inside straight to keep the Senate, and they did,” said Sherman, who writes Politico’s Playbook with Anna Palmer, Sherman’s co-author on The Hill to Die On. “They won in Maine. They won in North Carolina. They won in Iowa, and they won in Texas.”

Although Biden prevailed in Georgia, many of the voters who cast their ballots for the president-elect voted against Trump, not for Biden per se, and they are likely to vote for a Republican Senate. Georgia is, after all, a Republican-leaning state.

Sherman said, however, that Democrats could defy expectations and win both seats in Georgia, giving them a slight edge in the Senate with the tie-breaking vote of the vice president.

“Democrats can absolutely win,” Sherman asserted. “They will not have a lack of money. There will be tens of millions of dollars (spent in these races.)”

If, as expected, Republicans keep control of the Senate, Biden will take office with a divided Congress, the first time in many years an incoming president’s party did not control the House and Senate.

Infrastructure – the rebuilding of America’s dilapidated roads and bridges – is one area where both Democrats and Republicans could agree, opening the way for a bi-partisan initiative.

“If (Biden) gives Republicans ownership over infrastructure and over that process, he could get it done,” said Sherman.

But Biden will have to act quickly, “striking when the iron is hot,” within the first six months of his administration, according to Sherman.

“And he has to really get Republicans on board early,” he said.

Election Outcomes

Sherman discussed the results of the November elections, saying that this presidential election cycle, like the last one four years ago, proved the prognosticators and pollsters wrong.

“House Democrats were expected to win a bunch of seats, and expand their majority,” Sherman said.

But the Democrats lost seats, failing in the process to knock off a single Republican incumbent. 

“That is really an unfortunate result for (Democrats) – no matter what they say,” commented Sherman.

Congressional Democratic candidates ran on the issue of health care policy, a message that fell flat because many voters did not consider health care policy a top priority.

Although anti-Trump sentiments ran high on the presidential campaign level, it was not as pervasive in many congressional districts. As Sherman pointed out, “People wanted more.”

House Republicans ran on a “scare tactic,” accusing their Democratic opponents of being socialists who would turn the United States into a socialist country. That message resonated in many parts of the country.

Republican candidates also relied on large cash advantages in some areas to take the offensive and hammer their opponents.

Biden was able to beat Trump by winning large margins in urban and suburban areas, capitalizing on an anti-Trump vote to change the face of the political map, Sherman said. Suburban areas in Phoenix, Dallas, Houston, Charlotte and other places – once considered bastions of Republican support – went for Biden in big numbers, enabling the former vice president to prevail over Trump.

“The suburbs of all of those cities are turning very, very blue very quickly,” Sherman said.

Trump picked up support in rural areas, away from cities and suburbs.

“He tried to run up the score there,” Sherman said. “But that didn’t work.”

Trump’s Future

Many people ask Sherman about Trump’s future now that he has lost the White House. Even in defeat, Trump will continue, “to have control over the Republican Party for years to come,” predicted Sherman.

Sherman described Trump as “an ineffective legislative president,” a result of his inability “to stick to any topic for more than a day or two.” 

Nevertheless, “the Republican Party is 95 percent behind Donald Trump,” Sherman said. “He is the most popular Republican politician in our history.”

This is why the Lincoln Project – an anti-Trump Republican group—had very little impact on the presidential election despite actively campaigning against the president. 

“The anti-Trump Republicans represent a small sliver of the party at this point,” said Sherman in a response to a question about the Lincoln Project’s impact. “That might not be a popular thing to say, but it is just the truth.”

Trump would have had a “good chance” of winning re-election had it not been for the COVID-19 pandemic, Sherman said.

Moreover, if Trump “had come out early and said, ‘everyone needs to wear a mask,’ this would have been a different ballgame,” Sherman said. “Instead, he played kind of cute with it. He discouraged in some way, shape or form the use of masks, and I think that impacted (the election).”

After leaving the White House, Trump will probably reside at his Mar-a-Lago home in Palm Beach, Fla., while keeping his apartment in New York. Trump is already talking about running for president in 2024, a prospect that freezes the Republican presidential field, which is probably his intention, according to Sherman.

Trump is reportedly furious with Fox News and other conservative media outlets for not supporting him more vigorously for president. He may create a media empire of his own, and may or may not be involved in running it, Sherman said.

“He is going to be appearing on television, weighing in on governing, weighing in on Joe Biden and weighing in on legislating,” Sherman said. “I can’t imagine he is going anywhere.”

Sherman interviewed Trump for his book, A Hill to Die On, and according to Sherman, Trump “is far more interested in the media than he lets on.”

“He is interested in what the media says about him, what the media thinks about him, and what is written about him is something he focuses intently on,” Sherman said.

Labor of Love

When having political conversations with Sherman, one salient characteristic always comes through – Sherman’s love of covering Congress, especially the House of Representatives.

“The thing I love about Congress is that it is an evolving story,” Sherman said. “It is the closest story to the people – if that makes sense. It sways with the political winds of the country in a way that the White House does not.”

Sherman talked about the “physical nature” of the House, an institution “where people are packed together and are in constant contact.”

The COVID pandemic has robbed reporters and politicians of that closeness, an unfortunate development, Sherman said.

In October, Sherman and his writing partner, Anna Palmer, announced they were both leaving Politico at the end of the year, a “bitter-sweet” departure. Sherman started at Politico as a 23-year-old kid in 2009, covering House Republicans.

“They had me cover House Republicans because they were in the minority, and they figured I couldn’t screw it up too badly,” Sherman joked.

In 2016, Sherman began writing Playbook with Palmer, enhancing its status as the nation’s premier political newsletter. Playbook serves as a sort of cliff notes for the political day in Washington, a publication read religiously in the White House, on Capitol Hill and other places of influence such as law firms and lobbying agencies.

Sherman, at the time of this writing, had not publically disclosed where he will work after Politico. He said, however, “I will not be a wine critic so I will be in the same business doing something kind of similar but different at the same time.”

That Neighborhood Feeling

Like many writers who live in Cleveland Park, Sherman has found that the Cleveland Park village is conducive to his research and writing. He did much of the research and writing for his book at the Cleveland Park Library while sitting on one of the library’s balconies. One of the balconies looks out over Macomb Street where Sherman lives with his wife and children while the other balcony overlooks Newark Street.

“The library is an important part of my story – the story of the book I wrote and that experience,” he said, adding that the library is “an important institution for my family and me.”

During the question and answer segment, one viewer asked Sherman to name his favorite establishment in Cleveland Park, and without hesitation Sherman said the Cleveland Park Bar and Grill.

“I have been going to the Cleveland Park Bar and Grill for 15 years, for as long I could drink alcohol,” he said. “I love the Cleveland Park Bar and Grill.”