Issam Jouma used to be a supporter of the Syrian regime. He lived in Aleppo, the country’s commercial capital, and the center of much of its wealth. A dentist going about a nice life with his wife and five kids, like many Aleppo residents he thought things were okay under Syrian President Bashar al-Assad.

“I was very comfortable in general. There were small things we were uncomfortable about, but those things were out of our control. My financial situation was not bad. I had bread; I had gas. Everything was available. When I would go to government buildings, they actually helped me, because I’m a doctor,” Jouma says. “People were proud that Bashar was the president. He had a lot of support.”

Support for Assad was far from unanimous under one of the Middle East’s most repressive regimes—talk of dissent tended to be hushed, often with warnings that “the walls have ears.” But Assad was promising slow and measured change, and for people like Jouma that was enough. “Compared with the Arab leaders around us, we thought Bashar was honest,” he says.

The economy had also been opening under Assad. Businesses did well in Aleppo, either in spite of the rampant corruption that accompanied this economic push, or because of it. Often, financial success inspired support. Even as the uprising against Assad gathered steam, many thought Aleppo would hold up.

Instead, the city has become a focal point in an increasingly violent battle between rebel forces and the Syrian regime. Since a surprise rebel offensive took hold in Aleppo in July, the regime has reduced much of it to rubble, shelling civilians and rebels alike with heavily artillery and fighter jets. Amid the mayhem, much of the business that helped to define Aleppo has fled. So have former supporters like Jouma, who gave up on the regime over the course of its brutal crackdown against the revolt and finally fled to neighboring Turkey last month. “I still cannot believe that our country has come to this point,” he says.

The battle for control of Aleppo continues—on Friday, rebels launched what the Associated Press called a “major operation” with coordinated attacks on security sites around the city. Regardless of the outcome, though, the rebel push into Aleppo—and the destruction that has ensued—has already eliminated a key component of the regime’s support. “Assad had the support of wealthy businessmen, but this has eroded as the regime escalated its methods of attack—for example, helicopters and fixed-wing aircraft,” says Andrew Tabler, a senior fellow at the Washington Institute for Near East policy. “This put businessmen in a dilemma.”

Farzand Omar is a cardiologist who hails from a family of Aleppo businessmen. He says they have a maxim: “I don’t put my foot on shaking ground.”

“There is no emotion,” Omar adds. “They just follow their interests.”

Now that the ground is shaking, many have withdrawn their support, or simply fled, analysts say. Some in the opposition have been pleased with the result. As one member of Aleppo’s revolutionary council puts it, “Assad’s going to lose a lot of the finances that supported his regime.”

With the uprising grinding on and the ground in Aleppo looking as shaky as ever, though, this doesn’t mean Assad’s financial support in the city has switched over to the rebels—only that it’s gone. “The rebels made the regime lose the support of Aleppo,” says Salwa Ismail, a Middle East specialist with the School of Oriental and African Studies. “But that doesn’t necessarily mean the rebels gained the support of Aleppo.”

There is a dark side to Aleppo’s financial success. The city suffered badly under crackdowns by Assad’s predecessor—his father Hafez—for its resistance to his government in the 70s and 80s, Ismail notes. Aleppo was eventually “rehabilitated,” she says, but in many cases those who benefited were “the kind of people the regime always works with”—people connected to it.

“It created a new business class,” Ismail says, and the regime worked to benefit from them by making money from things like cuts, kickbacks, and partnerships. “If businesses are collapsing, or the people running them withdraw or flee, then it’s a loss for the regime itself,” she says.

To be sure, many businessmen in Aleppo weren’t tied to the regime. But even those who didn’t support it had to play by its rules. “The people in Aleppo are forced to deal with the regime,” says Mohamed Darwish, a long-time opposition activist who owned a small factory in Aleppo that made plaster for bandages.

Jouma’s brother, Wajih Jouma, who also fled last month, hated the regime but still worked his way to a prestigious government post as head of the doctors’ union in Aleppo. It’s better to have a good person in the position, he remembers telling himself as he climbed the ladder. (And indeed, some Aleppo doctors say it was invaluable having him in the post as they treated injured protesters and rebels, a dangerous act if done on the wrong watch.) “The game was like that in Syria,” he says. “We worked on possibilities, you know?”

Now the game has been upended. Much of the country is under siege, and the economic outlook is darkening fast—“the economy is tanking, and people are preparing for the worst,” Tabler says. Even Aleppo’s wealthy struggle with previously unheard-of problems like lack of water and electricity and waiting in line for bread, on top of a constant fear of the MiG fighter jets patrolling overhead.

Um Mohamed—the nickname given by one woman who fled Aleppo with her family last month—decided to leave after a shell fell near her backyard in an upscale neighborhood that she never expected the fighting to touch. She, too, considered herself a regime supporter until the picture she’d had of Syria was shattered by the uprising. “Before the revolution, people were living well.  They had a good situation. You had no reason to be against the regime. Then, when people started speaking against it, it killed them,” she says.

Sitting with her family at a café in Antakya, a Turkish city near the Syrian border, she says she’ll settle for nothing less than the overthrow of Assad. “How can we accept anything less?” she says.