When Legacy Becomes a Liability: What Simons and Hudson's Bay Teach Us About Retail Survival

I watched two Canadian department stores take opposite paths over 15 years.

One transformed retail spaces into destinations people wanted to visit. The other assumed its 350-year history would keep customers coming back.

By March 2025, Simons operated 19 profitable stores across Canada. Hudson's Bay filed for creditor protection with over $1 billion in debt, closing 74 of its 80 locations and eliminating 89% of its workforce.

The difference came down to how each company answered a basic question: what brings people into physical stores when they can buy everything online?

Simons Built Experiences Worth the Trip

Simons invested in making stores feel different. Each location featured unique architectural elements and art installations that turned shopping into something memorable.

The company spent over $150 million on a state-of-the-art distribution center to support seamless online and in-store integration. They curated a distinctive product mix with 70% private label merchandise balanced with contemporary designers.

This created a fashion identity you couldn't find anywhere else.

Peter Simons, the company leader, emphasized creativity, architecture, and art as core business strategy. The stores invited customers to linger and explore rather than rush through transactions.

The measured expansion approach kept the company financially stable. Simons grew to just 19 stores by 2025, selecting each location carefully rather than chasing rapid growth.

Research shows stores with experiential elements see 40% longer customer visits and 30% higher sales compared to traditional formats. Simons understood this early.

Hudson's Bay Relied on History

Hudson's Bay took a different approach. The company assumed its historical legacy would sustain customer loyalty without major reinvestment in the shopping experience.

The stores maintained outdated layouts while competitors modernized. The e-commerce platform remained clunky with poor integration between online and physical channels.

Management made acquisitions that prioritized financial engineering over operational improvements. These moves added debt without solving the core problem: customers had no compelling reason to visit.

The brand struggled with identity. Hudson's Bay got caught between serving its traditional customer base and attracting younger shoppers. This unclear positioning made the brand forgettable.

When the pandemic hit, it accelerated problems that already existed. The company couldn't pivot because it lacked the digital infrastructure and experiential appeal that might have kept customers engaged.

The Numbers Tell the Story

Simons invested $75 million to open two Toronto stores in 2025, creating 400 jobs. This represented part of a $300 million expansion over five years.

Private label products now account for 25% of retail unit volume across major sectors, with 57% of consumers viewing them as above-average value. Simons' 70% private label strategy positioned the company ahead of this trend.

Hudson's Bay carried $1.1 billion in debt by March 2025, including $724 million in mortgages and $405 million in credit facilities. The company recorded a $329 million net loss with just $3 million in cash.

The restructuring left approximately 2,000 creditors owed nearly $950 million, including major brands like Adidas, Nike, and L'Oréal.

What This Means for Your Business

The Simons and Hudson's Bay comparison offers clear lessons for any business facing digital disruption.

Experience matters more than convenience. Simons proved that physical retail works when you give customers something they can't get online. The art installations, architectural design, and curated product selection created reasons to visit beyond simple transactions.

Brand identity requires consistent investment. You can't rely on past success to carry you forward. Simons invested in brand identity through every store design decision. Hudson's Bay assumed its history would do the work.

Financial discipline enables growth. Simons chose measured expansion over explosive growth, keeping the company financially stable. Hudson's Bay pursued debt-heavy acquisitions that added financial pressure without solving operational problems.

Digital integration is table stakes. Simons spent $150 million on distribution infrastructure to support seamless omnichannel operations. Hudson's Bay treated digital as an afterthought, leaving customers frustrated with poor integration.

Clear positioning beats trying to serve everyone. Simons built a distinct identity as a trend-conscious modern Canadian retailer. Hudson's Bay got stuck between competing customer segments and ended up appealing to neither.

The Broader Pattern

This pattern extends beyond retail. I see similar dynamics in professional services, hospitality, and B2B industries.

Companies that invest in distinctive experiences and maintain clear brand positioning tend to weather disruption better than those relying on legacy advantages.

The pandemic didn't kill Hudson's Bay. It exposed weaknesses that existed for years. The company failed to evolve while customer expectations changed around them.

Simons succeeded because leadership understood that retail formats aren't obsolete. Uninspired retail is obsolete.

The stores that survive create experiences worth leaving your house for. They integrate digital tools seamlessly. They maintain clear brand identities that resonate with specific customer segments.

Most importantly, they invest consistently in these elements rather than assuming past success guarantees future relevance.

What You Can Do Now

Look at your own business through this lens.

Are you investing in experiences that differentiate you, or relying on legacy advantages? Do customers have compelling reasons to choose you beyond convenience or price?

Is your brand identity clear and consistent, or are you trying to serve too many different segments? Have you integrated digital capabilities seamlessly, or do they feel like an afterthought?

The answers to these questions matter more than your industry or company size.

Simons and Hudson's Bay started from similar positions. Both were established Canadian retailers with long histories. The difference came down to strategic choices about where to invest and what to prioritize.

One company bet on creating distinctive experiences and maintaining financial discipline. The other assumed its legacy would carry it through changing times.

By 2025, one was expanding. The other was liquidating.

The lesson is clear: in business, what got you here won't get you there. You need to keep investing in what makes you relevant, even when that means reimagining everything you've built.