Scott T Jackson for GA

GREENWICH, Connecticut — If you want to know how people on Wall Street are thinking about the election, go to an open bar in Greenwich.

“All of us would do better if one side wins,” one financier told me, referring to former President Donald Trump, as she made a circular gesture over the din of a cocktail hour on a dockside patio. “The rest of the country just might crumble around us.”

It’s hard to find a group of Americans with more conflicted interests in the outcome of this election than Wall Street’s bankers and financiers. On the one hand, members of the financial class prioritize profits, and Trump is offering to cut them good deals. On the other hand, they have a stake in the general welfare of the country, since a strong economy tends to boost their bottom lines and Vice President Kamala Harris’ pledge to deliver stability would help it expand.

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In that respect, in this election, Wall Street is a lot like a swing state. Trump’s promises to cut taxes and reduce regulation would be a boon for financial firms, and those promises have helped him rebuild the coalition of high-powered donors and financiers who supported him through his first term.

But when it comes to politics, financial pros crave certainty almost as much as they crave a decent catered lunch, and the former president’s erratic behavior — along with his fascination with ultra-protectionist trade policies that Wall Street hates — are a cause for concern for this crowd. That’s created an opening for Harris, who has courted industry leaders since she ascended to the top of the Democratic ticket. Fundraising surged as prominent Democrats on Wall Street signed endorsement letters and organized groups to drum up more support within the business community.

To gauge which message was landing with the monied class I decided to visit the Greenwich Economic Forum on Connecticut’s Gold Coast. The annual hometown event is, even by the standards of investment conferences, a placid affair, a space for economists and investors to offer anodyne observations about allocation strategies and private credit markets. It’s where people wait in line for former Commerce Secretary Wilbur Ross to sign copies of his new book, Risks and Returns: Creating Success in Business and Life.

But it’s also a place where you can get glimpses of the fortunes many have at stake. Outside a local museum where attendees gathered for welcome drinks was a 2025 Aston Martin Vantage, available for test drives. Private tours through a gallery with works by Andy Warhol were available upstairs. And beyond the patio at the Delamar Hotel where I spoke to the financier, yachts were moored in the harbor, glinting in the setting sun.

The financier, who like most of the people I spoke to at the forum asked not to be named so she could speak frankly, told me that clients have been inundating her firm with requests for how the outcome of the election could affect lending markets or the deal environment. The range of potential outcomes are too wide and depend not only on who’s in the White House but also control of Congress, regulatory agencies and the state of the economy.

“They truly don’t know,” she said. “No one really does.”

It’s not like the Biden years have been bad for Wall Street. Inflation, high interest rates and President Joe Biden’s regulatory agenda certainly dented their enthusiasm, but the economic anxieties that defined the post-pandemic era are fading. The stock market is routinely closing at record highs, borrowing costs are coming down, and banks are raking in fees now that trading and corporate mergers have started to rebound.

Last year’s Greenwich Forum was clouded by worries over how Washington dysfunction might trigger a shutdown and fiscal calamity. There’s a lot less “doom and gloom” this year, Rich Nuzum, the global chief investment strategist at the consulting firm Mercer, told me in an interview on the patio. On a day when the S&P 500 closed at a record high of 5,792, iCapital’s Anastasia Amoroso told the Greenwich crowd that the popular stock index could climb to 6,300 by this time next year.

The biggest risk to that sunny prediction is “probably the election,” she added.

That, in a nutshell, is the question the Wall Streeters packed around the Delamar’s patio bar were weighing: Will they vote for their own bottom lines or vote for the candidate they think will be the best steward of the overall economy?

Alan Patricof — a 90-year-old godfather of modern venture capital and a longtime Democrat — put it this way: A vote for Trump “couldn’t be anything else but thinking in your own pocketbook and not thinking about the country.” That view, he added, “doesn’t make me popular, by the way, with my brethren.”

The sun was not shining on the Delamar’s patio early that morning. Most of the conference goers were packed inside, and steam rose from my coffee cup as I watched Ray Dalio, the billionaire investor and commentator, teleconference into the forum from Singapore on a massive TV mounted across from the bar.

A Trump administration would be better for the markets, he explained. The former president’s policies are “more classically capitalist,” and while Trump’s plans to impose sweeping tariffs on imports might be inflationary, Dalio said he estimates they could raise hundreds of billions in revenue. Lower corporate rates and tax policies that avoid targeting wealthy populations are generally “more favorable” than what Harris has proposed.

But Dalio cautioned conference goers that his comments should be viewed only through the lens of the marketplace. There are other factors worth considering, he said — including whether there’s an orderly transfer of power. The Bridgewater Associates founder is famous for making dour predictions about looming conflicts but, this time, his forecast was a bit more urgent.

“It seems inconceivable that I would be asking that question,” he said, but the country is dealing with “irreconcilable differences, not just budget and economic differences” that could cause the federal government’s authority over the states to fracture.

Those existential questions about the future of the country weren’t top of mind for everyone at the cocktail hour that evening. One wealth adviser gasped at the possibility that Harris could charge taxes on unrealized capital gains — the so-called “wealth tax.” The adviser’s unprompted comments about a tax policy that Harris indirectly endorsed earlier in the campaign highlights how she is being perceived by a professional class whose raison d’être, after all, is the accumulation of wealth.

That extends even to Harris supporters in this crowd. One hedge fund founder — who told me he plans to vote for the vice president because of Trump’s extreme positions — said repeatedly that a second Trump administration would be a bigger boon to his fund. Similar tensions are playing out in public on the campaign trail. Mark Cuban, the billionaire investor who’s now a key Harris proxy to the business community, told an Arizona town hall recently that Harris knows taxing unrealized gains would be an “economy killer” and that she will not implement it.

At one panel, the audience laughed nervously when Rebecca Patterson, a former top investment strategist at Bridgewater Associates and Bessemer Trust, said that she didn’t want to give her forecast for how the market will perform next year until mid-January — that is, until after Congress officially tallies the electoral votes.

“I’m being dead serious,” she said, as the crowd hushed. “I think this election is incredibly consequential and depending on the makeup of Congress and the president, I could change my view completely.”

Patterson told me afterward that she’s skeptical Trump could carry through on his promises. For instance, it’s unlikely that Trump will be able to persuade Congress to lower corporate tax rates by as much as he’s proposed. But it’s hard for her to brush aside his threats to use his executive authority to impose restrictive immigration and trade policies on “day one” — policies that economists like Patterson see as damaging for the economy.

There has been a lot of media attention on the billionaire class during this election cycle, particularly now that moguls like Elon Musk and Bill Gates are plowing fortunes into groups that are working to swing the odds toward Trump or Harris.

Wall Street leaders are a little bit different from those billionaires. Bank presidents and hedge fund executives are hardly beloved by the public — few candidates brag about how their agendas will benefit high finance — but they’re generally viewed as having a stronger grasp of the forces that shape markets and the real economy. That’s why people put so much stock in their perspectives on the presidential race and its consequences.

Greenwich has been a bedroom community for Wall Street bankers and investors for more than a century. Major hedge funds like AQR Capital Management and Lone Pine Capital are headquartered in town. It’s the birthplace of country club Republicanism — the Delamar is less than two miles from George H.W. Bush’s childhood home. Both Greenwich and Wall Street donors overwhelmingly supported Mitt Romney in 2012, and both tilted blue — at least with regard to presidential politics — in 2016 as Trump put the party’s moderate wing in a hammerlock.

But although Trump was a departure from Republican orthodoxy, the former president’s policies were ultimately a boon for the financial industry. His signature 2017 tax law lowered rates for both top earners and corporations and created lucrative exemptions for estate taxes. Post-global financial crisis reforms to the banking sector were pared back over the objections of progressives like Massachusetts Sen. Elizabeth Warren (D). His appointments to agencies like the National Labor Relations Board and Consumer Financial Protection Bureau were hailed by pro-business groups, as were his efforts to slow down federal regulatory processes.

Trump’s “first term was less populist in practice than the markets or investors feared,” Nuzum told me. “There’s a thesis that that would be the case again.”

But Trump’s trade policies remain a sticking point for Wall Street. His tariffs kicked off an economically damaging trade war with China. His attempts to block immigration set off massive protests across the U.S. But ultimately, many Wall Street leaders “were willing to swallow trade policy, immigration policy and disruption to the international system” during the former president’s administration, the head of one major think tank told me earlier this month.

Wall Street welcomed Biden’s election, but his relationship to the financial industry soon curdled. As Biden’s approval ratings sank under the weight of inflation and high interest rates, financial industry donors like Blackstone Group founder Stephen Schwarzman and Nelson Peltz — who’d publicly repudiated Trump after the Jan. 6 riot at the Capitol — began to swing back into Trump’s camp. After the former president trounced Biden in a June 27 debate, Wall Street began to prepare for a Trump victory and loaded up on “Trump trades” that would perform well in a Republican administration. One investment strategist at the Greenwich conference told me that before Biden dropped out, the bulk of their work this summer had focused on preparing clients for the macro consequences of Trump retaking the White House.

Harris’ ascension to the top of the ticket turned the race into a coin flip. It also scrambled previously held notions about what four more years of Democratic leadership could mean for economic policy and regulation. Even though she’d run to the left of Biden during the 2020 Democratic primary, her relationships with Wall Street executives like former American Express CEO Ken Chenault and Lazard’s Ray McGuire have led many to believe that her administration would be more sensitive to industry perspectives than Biden’s had been.

The vice president and her campaign have gone to considerable lengths to reinforce that narrative. Harris has made the case that she prefers consensus and that she would solicit input from the business community — even Republicans — in crafting her agenda (much to the chagrin of Wall Street reformers and progressives). Proxies like Cuban say that she would govern as a pragmatist. Her plan to raise the corporate rates is more modest than what she proposed when she first ran for president, and she recently broke with Biden by rolling out a more moderate proposal for taxing investment gains.

So Harris has made inroads. Kathy Wylde, the president and CEO of the Partnership for New York City, a nonprofit organization that represents top executives at some of the city’s largest firms, told me that Republicans last May were arguing that “the threat to capitalism from the Democrats [was] more concerning than the threat to democracy from Trump.” But by this month, Wylde told me that many on Wall Street were now anxious about the unrest that could occur if Trump — once again — tries to undermine the election.

“What they want most is stability — political stability,” she added.

Stability, yes, but also certainty. A generic criticism of Harris I heard in Greenwich is that no one knows where she stands. Her views on economic policy have certainly evolved to be more business friendly — she no longer wants to fund Medicare for All with a tax on stock and bond sales — but some aren’t convinced.

“Some of the indications from her past are a bit worrisome,” said Gregory Lyons, who co-chairs the financial institutions at the white-shoe law firm Debevoise & Plimpton. “It could be pretty bad if she ends up defaulting back to this very, very progressive view of financial services.”

The final takeaway is that Wall Street’s preferred candidate isn’t in this race. The closest thing I could find to consensus in this particular swing electorate is a hope that control of Congress remains divided, with the House controlled by one party and the Senate controlled by the other. That way, Congress would impede the agenda of either a Trump or Harris administration, limiting their ability to deepen deficits, weaken markets or inflame the geopolitical landscape.

“Our clients would generally say they just want gridlock,” said Nuzum, adding that his firm’s clients are hopeful that either candidate would be forced to work with moderate members of Congress. “Gridlock is good for markets. Gradualism is good for capitalism.”