Hester's Relationship With Money.

In most of Hester's scenes, it's mostly been about money.

"No doubt they're hoping you can convince me to chisel open my casket of riches." - Hester
"I'm raising funds, not the dead. And besides, we both know you'd rather be buried with your millions."- Morticia in "If These Woes Could Talk"

"The four horsemen of the apocalypse would have to gallop through her tombstones before that woman gave a cent to this school." - Wednesday in "Woe Me the Money"

Obviously, this is used to highlight how greedy Hester is, but I feel like this is much deeper.

Usually, when a character is greedy or obsessed with their wealth in media, it's for a reason behind it. One of the reasons is that they grew up in poverty and are obsessed with never being poor again. Think of Mr. Kabs and Scrooge McDuck.

Hester fits this idea well.

Hester most likely grew up in poverty, moved to the United States, and eventually built her empire. "She built Frump Mortursties into one of the most successful Outcast-owned businesses in the country." - Bianca in "The Devil You Woe."

Hester also admits she was an "amateur tomb raider" in "Woe Thyself"; I wouldn't be surprised if she was a grave digger as well, which could potentially explain why she eventually entered the funeral business in the first place.

I also think her relationship with money is connected to her mother.

u/ElvenQueen726 made a post about the complex Mother relationships:
https://www.reddit.com/r/weyler/s/sQfbD1UG6M

I theorized that Hester's mother is the "Sacrificial Mother": a mother who sacrifices her own needs, dreams, and identity for her children.

If Hester grew up in poverty and had to watch her mother sacrifice everything without ever having financial security, Hester desired to be the exact opposite. She doesn't want to sacrifice her own ambitions. She wants a career, wealth, and the freedom that comes with financial independence.

That could also explain why she has such a strong reaction to Morticia's life.

In the comments, u/BeMore77 suggested that Hester sees a younger version of herself in Morticia.

I strongly agree; I think Hester sees a younger version of herself and her own mother in Morticia.

This would explain why Hester has such a problem with Morticia being a traditional and dutiful mother: "A woman should have a portfolio of her own, and not be reliant on a husband." - Hester in "These Woes Could Talk."

In Hester's eyes, Morticia's financial dependence on Gomez may represent everything she spent her life trying to escape from. She looks at Morticia and sees a woman who has willingly put her ambitions for her family, something Hester may associate with her own mother and the sacrifices she made.

And then there's Hester's relationship with her husband, the "huskter."

If Hester came from a wealthy background, I find it hard to believe she would fall for someone like him unless she was a grifter herself. Hester and her husband were most likely partners in crime before they became life partners. Thieves or grifters who worked together, stealing and robbing until falling in love.

During that time period, there were the Male Co-Signer Requirements. Women couldn't have their own business unless their husband, father, or even their teenage son co-signed the business loans. (Horrible, I know).

As u/ElvenQueen726 suggested, perhaps Hester and her husband were in business. Something happened that left Hester financially devastated. Maybe he took everything from her, or made a bad business deal, or gambled away their wealth.

If something like that happened, it could explain why Hester has a tight hold on her money.

She grew up with nothing. She watched her family scrape by and watched her mother sacrifice everything. She then potentially lost much of what she had built becuase of her husband. She rebuilt herself and created an empire.

In Hester's mind, financial independence equals freedom, security, and control, things she didn't have.