The Obama Problem

We have a lot to learn from both candidate and president Obama. A new generation of candidates is learning the wrong lessons.

The Democratic Party has an Obama problem. Whatever do I mean? I’m glad you asked.

Zohran Mamdani was on the brink of winning the New York City mayor’s race last November when he stepped off the campaign trail to handle something. He had gotten word that Chi Ossé, a Brooklyn councilman inspired by Mamdani’s own insurgent campaign, was building toward a primary challenge against Hakeem Jeffries. Ossé might have expected support from the man whose movement he had been part of.

Instead Mamdani called him the night before Election Day and told him he could not win, that a high-profile fight would undermine the left, and that if he persisted, Mamdani would ice him out completely. He also told Ossé he could be a key figure in the new administration, but only if he dropped the bid. When the call ended, an email was waiting in Ossé’s inbox. His invitation to Mamdani’s victory party the next day had been rescinded.

That was November. In February, Mamdani spent hours on the phone leaning on Working Families Party members to stay neutral in the governor’s race and protect Kathy Hochul from a primary challenge. When he got what he wanted, he called Hochul to make sure she knew his role. In January, Jabari Brisport, his former roommate and a senator who had spent years fighting for child care expansion, got moved out of camera range at the child care rollout because Hochul’s team asked and Mamdani’s office complied. He burned Nydia Velazquez, the first major elected official to endorse his mayoral campaign, by backing a different candidate for her congressional seat after she asked him to stay neutral. He showed up personally to the DSA meeting to kill the Ossé challenge. Ossé dropped out in December.

Last August I wrote that the worst thing Mamdani could do after winning was stand his movement down and try to negotiate his way to change. I said you cannot get small enough to become acceptable to people whose entire operation depends on things staying as they are. I said the only leverage that works is making them afraid of what happens if they don’t change. He had 50,000 volunteers and a million doors knocked and a city that had just told him it was ready. I am not going to pretend I called this wrong.

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The New York Times framed what he did as the portrait of a cunning operator. Jay Jacobs, the state party chairman who opposed Mamdani’s campaign, offered the lesson the Times seemed to endorse. Every successful political person has to be a little ruthless from time to time, Jacobs said. Otherwise you don’t survive.

That is not the wrong lesson because ruthlessness is bad. It is the wrong lesson because Mamdani is being ruthless in exactly the right direction for the wrong goal. He has power. He is using it. He is just using it to protect the people who stand between us and the change he ran on. Protecting Hochul and Jeffries is a choice. That million-door machine could have been aimed somewhere else.

The trap is not charm and it is not strategy. Both are tools and you need them. The trap is believing they are enough on their own, that if you are careful enough about managing your relationships with the people who currently have power, you can eventually get them to share it. That is not how power works. Power does not get shared. It gets built or it gets taken. A real supermajority, the kind that actually passes something, has never been built through accommodation. It gets built through aggressive political infighting, through primarying the members of your own party who are blocking your agenda, through making it more dangerous for someone to oppose you than to support you.

Democratic Senator Max Baucus had taken $3.2 million from the health care industry by the time he was handed the pen to write the Affordable Care Act. Obama let him write it. He wanted a seat at the table with the people who had spent decades building the table to keep people like him out. What he got was a health care bill that left the insurance industry intact, a stimulus too small to do the job, and a financial reform that left Wall Street standing after Wall Street burned the economy to the ground. Each of those got called a win. Each left the machinery in place. Last year I watched Democrats travel the country warning that the ACA subsidies expiring would be a healthcare catastrophe. What they were describing was Obamacare. The law they spent fifteen years calling a triumph. They passed something they knew was not good enough, called it a win, and watched it become the floor that everything else fell through.

FDR understood something about change that Obama and Mamdani have not. In the summer of 1938, after conservative Democrats in his own party started blocking New Deal legislation, Roosevelt campaigned across the country against his own incumbents. Reporters called it a purge. He mostly lost. But he understood that the fight for his agenda ran straight through his own party, and he was willing to say so out loud and pay the price. Trump understood the same thing from the other direction. In 2022 he backed challengers against Republican incumbents who crossed him, knocked out four of the ten who voted to impeach him, and remade the party in his image. Their vision is a list of enemies to hate. But both men proved the same thing. A party is not a sacred institution. It is a vehicle. And the people inside it blocking your agenda are the first fight, not the last. The progressive movement today operates as if it believes the opposite, and it keeps producing leaders who win elections and then protect the people standing in the way of everything they ran on.

What I have come to believe, from watching this up close for years, is that the most important thing about a candidate is not their policy positions. Policies can change. You can pressure someone into supporting a good idea. What you cannot inject into someone is a willingness to fight. Not willingness to fight Republicans on television, which costs nothing. Willingness to walk into a room where someone you thought was on your side is selling you out, say it out loud, and make them pay for it. Willingness to primary the colleague blocking the agenda you ran on. Willingness to point the movement at the people inside your own party who are protecting the system, because those are always the harder fights. You used to think those people were on your side.

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Either they have that core or they do not. And almost none of them do.

Once they have the office they decide they know better. They have a seat at the table. They think their job is to keep things running smoothly, not just for their constituents but for the movement. They worry that if they fail it will reflect badly on all of us. And that worry becomes the thing that makes them fail.

The people who knocked a million doors for Zohran Mamdani deserved to have that energy pointed at something after he won. They deserved to be the reason Jeffries had to think twice, not the force Mamdani used to make sure Jeffries never had to think at all. Chi Ossé deserved a mayor who understood that one more democratic socialist in Congress is worth more than a comfortable relationship with the House Democratic leader.

We have been living off the work of previous generations for a long time. The New Deal built the public infrastructure that made markets possible. The GI Bill built a middle class. NYCHA at its peak housed 600,000 people in dignity. Those generations understood that government had to build things, own things, make long bets. They sewed. We reaped. And somewhere along the way the Democratic Party forgot that you cannot keep harvesting from a field you stopped planting.

The leadership we have now does not have a vision for planting. When Trump froze two billion dollars in Harvard’s federal funding, Chuck Schumer announced that Democrats had sent a very strong letter asking eight very strong questions. When Trump deployed the military to Washington, Hakeem Jeffries praised a strongly worded letter from the DC Attorney General. Those are not opposition tactics. Those are the gestures of people who have made their peace with not having power.

Power is not winning. Winning is the beginning of the fight for power. The work does not stop on election night. It starts there.

I am not interested in being hard on Mamdani or Obama or any of the others. These are not bad people. They are people who believed that being in the room was the same thing as having power. It is not. Power is what determines what happens when you leave the room. And you build it before you sit down at the table, not by making yourself agreeable once you get there.

Corbin Trent

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I have been writing about this for over a year. The thing I hear most, from people who read every word, is some version of yeah, I get it, but what do we do about it.

A Fight Worth Having is being built to answer that question. We are working to find candidates who understand what this moment actually requires. Not just candidates who can win, but candidates who know what winning is for. We put them through a real process before we back them because the filter matters as much as the fuel.

• Are they ready to challenge Democratic leadership, not just Republican villains

• Are they willing to stand alongside candidates in other states and districts around a shared mission?

• Do they understand that their victory matters more if the person running three states over wins too?

When we find those candidates we go to work for them through independent expenditure campaigns. That is a legal term for us doing the work ourselves, separate from the candidate, without them having to ask. It means we can move fast, hit hard, and build the kind of infrastructure that the other side has been running for decades.

If you have been reading this and asking what do we do, this is what we do. Go to AFightWorthHaving.com and get in.