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Investors Poured $11 Billion Into 4 Retail and Real Estate Deals This Week, Plus Rite Aid, Bedrock and More

May 9, 2025

A capital infusion will help Wonder open a store a week, Nuveen Real Estate raised big money for its US Cities Retail Fund, Bill Ackman’s hedge fund bought another big chunk of Howard Hughes and Skechers is going private.

Wonder Raises $600 Million and Aims To Open a Store a Week

Wonder, which describes itself as “a new kind of food hall” and states it’s “creating the super app for mealtime,” just raised $600 million.

It owns restaurants, but its locations also sell meals from other chefs and restaurants. In November 2023, it bought Blue Apron, a popular meal kit-delivery company that provides Wonder customers a DIY option. In January, it acquired Grubhub, a major player in the third-party restaurant-meal delivery sphere that contributes restaurant relationships and its delivery platform. And in March, Wonder acquired media company Tastemade, availing itself of a content studio. Each of these acquisitions also brought more consumers into the fold.

Above: Wonder’s Clinton Hill, Brooklyn, location. At top: its store in Downtown Brooklyn

Above: Wonder’s Clinton Hill, Brooklyn, location. At top: its store in Downtown Brooklyn

And now this week, it announced it raised $600 million from existing shareholders led by New Enterprise Associates; Accel; GV, formerly Google Ventures; and Forerunner, as well as from strategic investors like Amex Ventures. “We plan to use this latest raise to continue accelerating the expansion of our physical retail locations, opening one a week with plans to grow from our current base of 46 locations to 90+ by the end of 2025,” founder Marc Lore wrote Tuesday on LinkedIn. “We’re excited to bring Wonder to more communities throughout the Northeast, and are focusing on our expansion into Philadelphia and D.C.”

Nuveen Real Estate Raises $320 Million for Its U.S. Cities Retail Fund

Institutional investors have added $320 million to Nuveen Real Estate’s U.S. Cities Retail Fund, which launched in 2018. The investment manager will use the funds to acquire “grocery-anchored, necessity-based retail across top U.S. neighborhoods,” the company stated, adding: “The strategy focuses on high-liquidity markets where consumers live and work, and where well capitalized retailers are looking to expand.” Nuveen’s website describes the open-ended fund’s targets as “core institutional-quality assets” that “have proven resilient across cycles and benefited from changing consumer demand.”

Nuveen, a subsidiary of TIAA, has $8 billion of retail assets under management. “Institutional capital is increasingly recognizing the resilience of necessity-based retail,” said Nuveen Real Estate senior director and portfolio manager Brian Wallick. “We are also seeing an abundance of lender appetite in this space, providing an ability to maximize risk-adjusted returns, while also creating real and efficient fund scale.”

Pershing Square Pays $900 Million To Up Its Stake in Howard Hughes

Billionaire hedge fund manager Bill Ackman is forging ahead with his vision to form what MarketWatch has cited as a “modern-day Berkshire Hathaway,” the investment conglomerate that billionaire Warren Buffett will continue to lead as CEO until he steps down at the end of 2025. Publicly traded Howard Hughes announced this week that Ackman’s Pershing Square has agreed to buy 9 million newly issued shares of Howard Hughes for $900 million. The deal will give Pershing Square a 46.9% ownership stake in the developer of master-planned communities, retail properties and other real estate projects. With a current stake of 38%, Pershing Square is already Howard Hughes’ largest shareholder, according to Investing.com.

Howard Hughes said the transaction will enable it to transform into a holding company, a la Berkshire Hathaway, that will own “controlling stakes in high-quality, durable growth public and private operating companies” yet continue developing master-planned communities and other real estate projects.

Ackman, who is chair and CEO of Pershing Square, also will serve as executive chair of Howard Hughes once the $900 million deal closes. He is no stranger to Howard Hughes, having chaired the company from 2010, when mall operator General Growth Properties spun it off, through 2024. Pershing Square chief investment officer Ryan Israel will assume the same role at Howard Hughes. The company said the remainder of the Howard Hughes executive team, led by CEO David O’Reilly, will stay in place.

Skechers Will Go Private in a $9.5 Billion Deal

Skechers opened on Milan shopping thoroughfare Corso Buenos Aires in February.

Skechers opened on Milan shopping thoroughfare Corso Buenos Aires in February. Photo courtesy of Skechers/Business Wire

Publicly traded footwear retailer Skechers, which operates more than 5,300 stores, is going private in a cash deal that Footwear News reported is worth more than $9.5 billion. Skechers said this week that private investment firm 3G Capital agreed to buy the brand for $63 per share, representing a 30% premium. Skechers racked up a record-breaking $9 billion in sales in 2024. Skechers said it and 3G Capital “have a shared vision for the long-term future growth of the business.” It’s unclear whether that vision will adhere to a goal Skechers outlined last year to eventually operate 10,000 stores around the world.

Rite Aid Again Files for Chapter 11 Bankruptcy Protection

Photo credit: JHVEPhoto - stock.adobe.com

Amid ongoing woes for major drugstore chains, Rite Aid plans to close or sell its more than 1,200 U.S. stores after filing again for Chapter 11 bankruptcy protection, Bloomberg and Reuters reported. Rite Aid filed for bankruptcy this week, following its September 2024 emergence from a bankruptcy case filed in October 2023. During the previous bankruptcy, Rite Aid slashed $2 billion in debt and closed about 850 stores. “But it wasn’t enough,” Bloomberg reported. “The pharmacy still carried more than $2 billion in debt and has struggled with weaker demand and inflationary pressures.”

As Rite Aid works through its second bankruptcy, drugstore chain Walgreens Boots Alliance has agreed to be acquired by private equity firm Sycamore Partners in a deal valued as high as $23.7 billion. Meanwhile, drugstore rival CVS is shutting down 270 locations this year.

Retailers Have Started Signing On to Bedrock’s New Mixed-Use Project in Detroit

The massive Hudson’s mixed-use project in Detroit has secured its first retail tenant. In a LinkedIn post, developer Bedrock revealed Alo Yoga as the downtown project’s first retail occupant. The athleticwear brand will open at the historic site of the former J.L. Hudson department store, which closed in 1983. “Detroit is brimming with purpose and Alo’s dedication to wellness and community complements the city’s vibrancy and growth,” said Naumann Idrees, senior vice president of leasing for Bedrock, which is based in Detroit and Cleveland.

The Hudson’s project, which the Detroit Free Press reported carries a $1.4 billion price tag, will span more than 1.5 million square feet across two buildings. The office component will be anchored by the global headquarters of automaker GM, which is vacating downtown Detroit’s Renaissance Center. In addition to ground-floor retail and a 12-story office building, Hudson’s will feature ​​the Detroit Edition hotel, a rooftop bar, condos and event space.

Construction on the project started in 2017 and is expected to be finished by year’s end, according to the Detroit Free Press. Dan Gilbert, whose net worth the Bloomberg Billionaires Index pegs at nearly $30 billion, is founder and chair of Bedrock and founder and majority owner of Rocket Cos.

Dressbarn Co-Founder Roslyn Jaffe Has Died

Discount retail pioneer Roslyn Jaffe, co-founder of the Dressbarn women’s apparel chain, died on April 12, The Wall Street Journal reported. She was 96. A celebration of her life was held on April 17 at Temple Sinai in Stamford, Connecticut. She and her late husband, Elliot, opened the first Dressbarn store in 1962 in Stamford.

Dressbarn became the foundation for a Jaffe retail clothing empire that grew to include Ann Taylor, Lane Bryant and Loft. Eventually, the Jaffes’ brands fell under the corporate name Ascena Retail Group. “At its peak, it operated nearly 5,000 stores and was one of the nation’s dominant retailers of women’s apparel,” WSJ reported. In May 2019, Ascena announced it would close all 650 Dressbarn stores. Retail E-Commerce Ventures then acquired the name and intellectual property rights, according to Forbes, and the name lives on online.

Aside from being retail entrepreneurs, the Jaffes have been major philanthropists. For instance, The Jaffe Family Foundation has established a $250,000 endowment with the ICSC Foundation for the Roslyn & Elliot Jaffe Retail Entrepreneur Prize. Undergraduate and graduate students passionate about launching a new retail concept, product, idea or pre-seed stage company compete each year for the $10,000 prize.

—Additional reporting by Commerce + Communities Today editor-in-chief Amanda Metcalf

By John Egan

Contributor, Commerce + Communities Today

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