Insurance and financial services giant Prudential is close to completing a deal to move out of the Chicago office complex that has carried its name since the 1950s, setting the stage for major changes as the owner of the two-tower Prudential Plaza looks to recapitalize the property.

One of the most noticeable changes will be the removal of Prudential's huge blue sign near the top of the One Prudential tower, which has been visible on Chicago postcards and skyline shots for decades.

The Newark, New Jersey-based company is in advanced talks to lease a full floor, or almost 28,000 square feet, in the 54-story tower along the Chicago River at 150 N. Riverside Plaza, according to people familiar with the situation. That tower is directly across the Loop business district from Prudential's longtime home along North Michigan Avenue and Millennium Park that it's giving up.

Prudential’s negotiations extend a trend of city business tenants in recent years eyeing smaller spaces in top buildings as leases expire, causing Chicago’s trophy office towers to outperform an overall sluggish leasing market.

Developed by Chicago’s Riverside Investment & Development, 150 N. Riverside is known for its thin, wedge-shaped base. The nearly 1.25 million-square-foot building, which opened in 2017, is more than 97% leased, according to CoStar data.

If a deal is completed as expected, Prudential would leave behind about 50,000 square feet in Prudential Plaza. The property, in recent years, also has been referred to as One Two Pru after Prudential stopped paying for naming and sign rights.

One Prudential Plaza opened in 1955 as the headquarters of Prudential’s Mid-America company and the second tower was added in 1988. One Prudential’s exterior is etched with Prudential’s Rock of Gibraltar logo and a Prudential sign is illuminated near the top.

Multiple Prudential businesses these days occupy space in the taller, newer tower at 180 N. Stetson Ave.

The approximately 2.3 million-square-foot complex is owned by Wanxiang America Real Estate.

That firm, a Chicago-based real estate affiliate of a Chinese auto parts maker, also was Riverside’s investment partner on the development of 150 N. Riverside. Wanxiang also occupies office space in the tower.

Wanxiang Managing Director Larry Krueger declined to comment specifically on the 150 N. Riverside deal, but he told CoStar News that his firm “fought hard to keep Prudential” at its longtime home.

“Once it was confirmed by the company and by its brokerage team that they were not going to stay, we felt it was OK to pursue another market deal” with Prudential, Krueger said.

Prudential’s expected move means that big, illuminated Prudential sign and other signs throughout the property could come down in the months ahead, particularly if signage rights are negotiated with a new tenant as Wanxiang and One Two Pru investment partner Sterling Bay seek to fill large blocks of vacancy.

The pending lease involving Prudential and Wanxiang at another building hints that there is no lingering bad blood between the two sides from a 2020 lawsuit regarding sign rights at One Two Pru.

Crain’s Chicago Business at the time reported that Prudential had sued Wanxiang and Sterling Bay over negotiations for a potential renewal of signage rights, with the complaint alleging that the property owners had made a $10 million offer for Prudential to be able to keep signs throughout the property. As is common with naming and rights to signs, the tenant was given the opportunity to either pay that amount or to be written a check for the same amount by the landlord to terminate branding rights.

The lawsuit, filed just months into the pandemic, alleged that the Wanxiang-led venture never paid the $10 million.

Krueger said the lawsuit was resolved in a recent settlement. He declined to comment on specific terms, but he said it included payments to Prudential and “the ability for us to re-sign the exterior of the building,” potentially as a perk for a new tenant. Some variation of the Prudential name will remain on the property, as it does now with the One Two Pru branding, Krueger said.

“It’s up to us to remove the signs when we find a suitable replacement,” Krueger said. “The Rock’s going to stay because it’s really a landmark. We don’t want it to be removed and Prudential is not requiring us to remove it.”

As reported earlier this year by the Chicago Tribune, Wanxiang also is in the process of trying to negotiate a modification and extension of four or five years on its commercial mortgage-backed securities loan for One Two Pru. There is more than $385 million remaining on the loan now scheduled to mature in August 2025, according to CoStar loan data.

The loan was moved to special servicing as part of negotiations.

“We’re very close to resolving that,” Krueger said. “It’s going to be a positive outcome.”

Riverside Investment & Development declined to comment on the 150 N. Riverside deal. Prudential did not respond to a request to comment from CoStar News.

The largest tenants at 150 N. Riverside are the global headquarters of William Blair and Hyatt Hotels.

The tenant is represented by JLL broker Eddie Viliunas. The landlord is represented by Riverside brokers Christy Domin and Drew Nieman.