When to Hold, When to Fold, When to Play a Different Game

Leading an arts organization right now can feel like sitting at a blackjack table on a bad night. The stakes are high, the cards aren’t great, and the audience—the one group you can’t bluff—can see every move you make.

When to Hold (on to your values)

All we really have with our audiences is trust. That’s why the Smithsonian needs to hold its independence like a winning hand. No bluffing needed – smile, look the other players directly in the eye and let them know you’ve got a winning hand. The players with the weak hand will fold.

In late March, President Trump signed a sweeping executive order, Restoring Truth and Sanity to American History, directing the Smithsonian to purge “divisive narratives,” “improper ideology,” and exhibits he deemed insufficiently patriotic—specifically targeting hard truths about slavery, systemic racism, and gender identity. In August, he then pressed for a top-down review of the Smithsonian’s public content—spanning museum exhibits to educational materials—to realign everything with a rose-tinted version of American exceptionalism, and followed it up with a list of specific art works and exhibits they wanted reviewed.

Here’s what we all need to remember: President Trump does not have any direct authority over the Smithsonian. The Board of Regents of the Smithsonian holds that power. He can issue all the executive orders he wants, but they don’t carry the authority to rewrite history to his liking. In this area, his executive orders have as much impact as if I wrote an executive order.

In addition to the formal power he’s trying to grab, President Trump is trying to grab cultural power he doesn’t have. The public isn’t on board with Trump’s Smithsonian rewrite. Most disagree with his framing of the Institution as “out of control,” firmly oppose government control over museum content, and overwhelmingly support museums that honestly represent both the nation’s pains and accomplishments. According to a YouGov poll conducted in late August:

• When asked to respond to Trump’s post claiming the Smithsonian is “out of control”—too focused on slavery and negativity—only one-third of Americans (33%) agreed, while a solid majority (50%) disagreed (combining “somewhat” and “strongly disagree”)—and 16% were unsure.
• On the broader question of whether the federal government should control what’s shown in federally funded museum exhibits, 60% said “no”—that’s the average of a widely cited majority opposed to government control. Only 18% supported the idea, while 22% were uncertain.
• It’s also worth noting Americans place high value on museum integrity: 84% believe it is “very important” for history and cultural museums to accurately represent American history, and similarly strong majorities (60–61%) believe they should also highlight both America’s struggles—including slavery, racism, inequality—and its achievements.

In addition to historians, cultural leaders, and regular Americans imploring the Smithsonian leadership to push back on the paper tiger, Democratic leaders entered the conversation last week with a letter to Smithsonian Secretary Lonnie G. Bunch III encouraging him to continue asserting the institution’s independence and affirming clearly that it’s Congress that oversees the Smithsonian via the Board of Regents, not the Executive Branch.

The Smithsonian is in a strong position to hold its ground.

(If you want to read my thoughts about another major cultural organization and holding on to integrity, read my recent post on my website about the Metropolitan Opera and its deal to perform in Saudi Arabia.)

When to Fold (or Fold Together)

Other institutions, though, face a different calculation: when survival is at stake, the question becomes whether to fold—or fold together.

Pittsburgh’s producing theaters are talking merger. Pittsburgh’s three largest theaters that produce their own work — Pittsburgh CLO, Pittsburgh Public Theater, and City Theatre — are all facing steep deficits, rising costs, and shaky attendance. A consultant’s report warned they’re each on the brink of financial failure within 2–5 years unless structural changes are made. The report recommends exploring a merger under one umbrella organization, while still maintaining the three brands. That could mean fewer staff, fewer productions, and shared administration to cut costs. Philanthropic foundations have already committed funds to continue the process with a study that digs into the legal and financial implications.

The stakes are high: if the merger goes forward and succeeds, it could be a national model for regional theaters in crisis. If it doesn’t, the report bluntly warns, at least one and possibly all three theaters could close.

I see the fragility of the nonprofit theater sector as part of the historical narrative of our field.  Some still want to blame the malaise of nonprofit theater on COVID. But we’re beyond the crisis recovery window. These are the last gasps of the era that began with the Ford Foundation investments in the late 1950s, the founding of the National Endowment of the Arts, and the regional theater movement going into the 1970s.

Today, niche rules. Engagement and relevancy rules. Agility rules. A sharp idea, executed well, can cut through without the bloat of a sprawling, obligatory season. Institutions clinging to the “classic model” are like players who won’t leave the table even as their chips disappear. Sometimes folding – or folding organizations together – is the smartest play.

Pittsburgh is my hometown. My love for theater – and therefore one of the biggest parts of my life – was formed at Pittsburgh Public Theater and City Theatre.  But nostalgia is a lousy business plan. I’m more comfortable with the idea of creative destruction and leaning into the opportunity of change than many other people, clearly.

I have the personal experience of having the responsibility of making sure an organization stays alive. That experience allows me to call out the futility in trying to hang on to what’s clearly not working anymore: not working for artists, for staff, for audiences, for donors, for communities. I don’t know if merging or closing is the right answer for these organizations, but I do know that leadership means tough decisions in the face of real circumstances. I wish them the best and hope they are getting wise, eyes-wide-open counsel.

When to Play a Different Game

Regional theaters may be struggling to keep shuffling the same tired deck, but other artists are proving you don’t have to play by the house rules to win. In this time of massive change, the smartest play can be to get up, walk away, and sit at an entirely new table.

Artists have always hacked the system, but the new tools make the hacks louder, faster, and more effective.

This past weekend in Chelsea, a new kind of art fair rolled up—literally. The U-Haul Art Fair parked ten moving trucks just south of the Armory Show and turned them into pop-up galleries, each outfitted with white-box interiors and filled with work from artists, galleries, and collectives. With its cheeky, low-overhead approach, U-Haul Gallery, a commercial venture, flips the script on the exclusivity and expense of traditional fairs, giving visibility to artists who might not otherwise get past the velvet rope. It’s guerrilla satire and genuine exhibition all at once—and it’s already planning to take the show on the road to London and Paris.

Or look at Jorge Rivera-Herrans with Epic: the Musical. It’s a nine-part, sung-through concept-album adaptation of Homer’s Odyssey, written, produced, and largely performed by Puerto Rican creator Jorge Rivera-Herrans (though it looks like there were other creators involved earlier on…and some related legal issues). Released between 2022 and 2024 as a series of “sagas,” it takes Odysseus’s odyssey into a mash-up of modern musical theater, anime, and video-game culture. (Here’s a video explainer.)

Rivera-Herrans documented his process on TikTok starting in 2021, staging auditions, sharing songs in real-time, and inviting fans into the creative journey. He has tens of millions of views, over a million Spotify listeners, rivaling mainstream cast albums.

Epic simply bypasses gatekeepers, which I’ve written about before as a necessary skill for artists today. He didn’t wait for a producer or a premiere slot. He wrote The Odyssey as a musical in public, on social media, for four years. He crowdsourced casting ideas, released songs piece by piece, and built an audience that’s both invested and enormous. He’s proof that if you treat your process like the product, you don’t have to beg gatekeepers to notice—you bring your audience with you from the start.

With its open process, it goes beyond normal blending of genres in the piece itself to being a prime example of how the process and product and audience are inextricably linked. Whether or not you like Epic as a piece of art, the open process is something that those of us who started making work in the last century should seek to understand.

The Game

Hold when it’s about trust. Fold when the old structures are crumbling. And if the game itself is rigged, play a different one. In the arts, the secret is knowing when to stop hoping for better cards—and start shuffling a new deck.