Prudential Plaza Owner Sues Legendary Chicago Restaurateur

A blockbuster restaurant deal that was supposed to help anchor a post-pandemic recovery at Prudential Plaza has curdled into a $1.2 million legal brawl.

Wanxiang Sterling Stetson Owner, LLC, the ownership entity for the iconic Chicago office towers at 130 East Randolph Street, filed a lawsuit this week against legendary restaurateur Alex Dana and his Rosebud restaurant entity that ran a three-level location within the building from 2022 to 2025.

Dana is the force propelling the well-known Rosebud and Carmine’s Italian restaurant brands that have multiple locations throughout Chicagoland, including a Carmine’s at 1037 North Rush Street that was recently renovated to the tune of $4 million.

Wanxiang, an affiliate of a Chinese auto parts conglomerate with a major commercial real estate investment arm led by Chicago-based Larry Krueger, seeks a seven-figure sum in damages for Dana’s and Rosebud’s alleged breaches of lease terms that it claims cost substantial expenses for repairs.

Rosebud and Dana didn’t return a request for comment sent to the restaurant group’s corporate office through its website’s contact form. Krueger and attorneys for the landlord didn’t return requests for comment made via email, text message and voicemail.

Wanxiang co-owns Pru Plaza with Sterling Bay after buying it for $680 million in 2018.

The dispute marks a bitter turn for the Rosebud lease that began with high-octane hype. In early 2020, just before the pandemic decimated downtown foot traffic, Dana announced Rosebud would take over the former Tavern at the Park space within the 2.3 million-square-foot office complex. The 18,500-square-foot, three-story trophy space overlooking Millennium Park was seen as a timely vote of confidence by Rosebud in the Loop’s retail future.

However, the white tablecloth dream allegedly became a nightmare. Friction peaked in February 2025 when the heat failed on the restaurant’s third floor, according to the complaint filed Wednesday in Cook County Circuit Court. Rather than alerting the building’s engineering team, Rosebud reportedly attempted a do-it-yourself fix, allegedly in breach of its lease with Wanxiang. The botched reheating caused frozen sprinkler lines to burst, triggering a catastrophic flood that the landlord claims Rosebud failed to properly mitigate.

The financial fallout is just as messy. Wanxiang alleges Rosebud stopped paying rent in January 2025 and occupied the premises for nearly 10 months without payment before the landlord finally terminated the 15-year lease for cause in October. The outstanding tab for rent and late fees currently approaches $500,000. Most explosive is the claim that Rosebud and Dana falsely blamed repair delays on slow insurers while allegedly secretly pocketing two payments in April 2025 totaling $471,036 — funds the lease required they assign to the landlord for building remediation, according to the suit.

The legal firestorm comes at a precarious time for the property. Wanxiang in early 2024 narrowly avoided a financial cliff, committing $50 million for an overhaul of the complex to secure an extension on its $389 million commercial mortgage-backed securities loan maturity, from 2025 to 2027, with options to extend again until 2029. The property had been sent to special servicing in June 2023 for “imminent monetary default” before being returned as a “corrected mortgage” in early 2024, according to loan servicer notes collected by Morningstar Credit.

Despite securing a win by landing architecture firm HOK as a tenant in 2024, the complex is still feeling the office market squeeze hampering much of downtown Chicago. Occupancy at Prudential Plaza fell to 68 percent for the 12 months ended Dec. 31, 2025, down from 75 percent in 2023, according to loan servicer data. While the property generated $74.7 million in revenue and $37.5 million in net operating income last year, effective gross income was down nearly 10 percent year-over-year, loan data shows.

Wanxiang and its building management partner, Sterling Bay, also settled a lawsuit the property’s previous namesake tenant Prudential Insurance brought against the landlords in 2020 over an alleged failure to pay $10 million breakup fee for the complex’s naming rights. Terms of the settlement, which was approved by the court in late 2023, haven’t been publicly disclosed.