A flurry of executive orders, a pared-down inner circle, and a White House driving change at breakneck speed have set the tone for the first 100 days of Donald Trump’s second term. With over 110 executive orders issued in less than three months, federal agencies, contractors, and lawmakers are navigating a complex new landscape. The implications span federal grant freezes, tariff swings, and a regulatory rollback with far-reaching impact.
In a recent Venable webinar, partner Ron Jacobs spoke with senior advisor and former U.S. senator Dean Heller and senior policy advisor Marco Sylvester about how these early moves are reshaping Washington.
According to Heller, a key difference from Trump’s first term is access: “That circle has shrunk dramatically... the decisions that are being made are made from the top.” Sylvester agreed, noting that a smaller, more loyal team “resulted in a much better prepared White House staff with ready-to-go executive orders, ready-to-go policy documents.”
Tariffs and Trade Policy Create Uncertainty for Corporations
Economic policy has been one of the more volatile areas of early governance, with panelists pointing to whiplash-inducing shifts in tariff structures. “We have Republican legislators on record saying tariffs are tax increases,” Heller noted. “And yet here they are supporting…the president.”
Sylvester outlined three competing schools of thought within the White House: the “Friedman-esque, low tariffs” philosophy of Elon Musk,” Treasury secretary Scott Bessent “pushing the White House to…preview the end game for companies and for the public,” and trade advisor Peter Navarro’s “substantial tariffs long term” policy.
According to Heller, this tension leaves corporate America with “a slingshot of just one way or the other,” especially with major businesses recalibrating branding to tout “American built for Americans.”
Reconciliation and Deregulation: What’s Next in Trump’s Agenda
Looking ahead, the administration’s focus will pivot to reconciliation legislation covering taxes, energy, and immigration. Sylvester explained the goal: Extending the Tax Cuts and Jobs Act, additional funding for deportations, and adjustments to the 2021 inflation reduction act. Heller added that execution will depend on timing: “I think they’ll be lucky to complete it by the August recess.”
Meanwhile, aggressive deregulation is under way. Jacobs described a recent executive order on deregulations as telling executive agencies, “Here’s a list of about 10 Supreme Court precedents from the past five to ten years about unlawful agency action. Go and repeal all your regulations that would be subject to those decisions.”
Heller described the broader strategy as “the art of the deal,” where President Trump takes issues to a certain level “only to ratchet it back to get what you want. And I think Trump is very, very good at that. You’re seeing that on tariffs right now.”
As the unitary executive theory redefines the balance between Congress and the White House, the panelists stressed the importance of relationships and understanding the administration’s inner workings. “It’s important to have representation that understands the administration,” Sylvester said. “Sometimes you may need a translator.”
This webinar was part of a weekly webinar series, Transition Outlook: What to Expect from the Second Trump Administration, that ran from December 2024 to April 2025. To read recaps of other webinars in the series, or watch recordings of the webinars, click here.