The sun was setting on the analog age. But Tribune’s Royko and Landers kept the pulse of Chicago.

One of the most momentous changes in the long history of the Tribune took place on Sept. 19, 1982, and almost none of the paper’s more than 1 million Sunday readers noticed.

On that day, the presses stopped running in the bowels of the Tribune Tower, where the newspaper had been printed since Dec. 12, 1920. Future editions of the paper would be printed and distributed from a new 700,000-square-foot plant on the banks of the North Branch of the Chicago River, a “state of the art” facility where the papers would be printed, collated, baled and relayed to delivery trucks that would transport them with computerized efficiency.

The newspaper had purchased the 21-acre property in 1967. Ground was broken in September 1979, and the local architecture firm Skidmore Owings & Merill designed the building. On July 15, 1981, the Tribune announced that it would be known as “Freedom Center,” a name suggested by the environment editor at the time, Casey Burko.

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There was a downside to this change. It came on July 18, 1985, when three unions went on strike, due to the mandatory transfer of jobs when the new technology of Freedom Center made obsolete many positions that had been held by union members.

On Jan. 4, 1986, a rally took place during the strike. Bricks were thrown and several people and a few delivery trucks were harmed.

Change is rarely easy, and in the last two decades of the 20th century changes came fast and steady for the Tribune and on all fronts for the city and the planet.

In the wake of the death of Mayor Richard J. Daley, there was political peace for a short while. That lasted until long-shot candidate Jane Byrne beat incumbent Mayor Michael Bilandic to become the city’s first female mayor.

The oft-cited reason for and certainly a contributing factor in her win was Bilandic’s inability to deal with the 20.3 inches of snow that fell on Jan. 13-14, 1979, which left residential streets clogged, schools inaccessible and garbage uncollected for over a week.

Byrne’s short tenure and tumultuous one term was symbolized by her move with her husband into an apartment in the Cabrini-Green public housing project. She did this, she said, to highlight the shabby and dangerous conditions there and in the city’s other looming high-rise public housing buildings. Critics labeled it a publicity stunt and though elevators were fixed, trash picked up, and violence stopped for a time, Byrne was out of Cabrini after three weeks and back in her Gold Coast apartment.

Byrne lost the next mayoral election to the charismatic Harold Washington, who was the city’s first Black mayor and would be the center of what became the “Council Wars,” an ugly three-year-long racially polarized political conflict. Washington would die of a heart attack just months into his second term.

By century’s end, another Daley, Richard M., was on the fifth floor at City Hall. Having moved in in 1989, he would remain there a decade into the new century, overseeing a period of revitalization that would transform downtown into a tourist destination, using the same iron fist as his father.

Politics, as ever, dominated the local scene, but other “sports” enlivened the city, especially the Bears’ 1986 Super Bowl victory with a team filled with colorful characters, and the genius of Michael Jordan, leading the Bulls to six NBA championships between 1991 and 1998, with two three-peats. “He’s a work of art,” the Tribune’s Bob Verdi wrote. “But he’s also about the art of work.” (My colleague Paul Sullivan artfully captures the city’s rich sports history in today’s Vintage Chicago Tribune).

For all of the buoyant news, there was also tragedy. The mere mention of the name Gacy should give you chills as might also the Tylenol murders and the Brown’s Chicken massacre. Remember the crash of Flight 191? The 1995 heat wave that killed more than 700 people?

If you lived here in the last decades of the last century, your memories are filled with a vivid mix of the good and the bad and the ugly.

You can remember the Loop in shabby times (and when the flood came in 1992), the vanishing of venerable manufacturing businesses such as the steel mills to the southeast, and the appalling cycle of violence that claimed the life of 7-year-old Dantrell Davis at Cabrini-Green in 1992 and spurred the Tribune’s “Killing Our Children” series the next year.

Through these years no one was a more astute observer than columnist Mike Royko. He had started his career at the Chicago Daily News and when that paper folded had moved his column to the Sun-Times. He had once been an admirer of Byrne but soon was calling her “little Miss Sourpuss.”

In 1984, Royko came “across the street,” as it was said, joining the Tribune after the Sun-Times was purchased by Rupert Murdoch, citing his reason by memorably saying, “No self-respecting fish would want to be wrapped in Murdoch’s publications. He publishes trash.”

Royko’s arrival, said then-Tribune editor Jim Squires, “means that the best Chicago columnist and the best Chicago newspaper have finally gotten together. It is about time.” And two years later Royko was joined by another major star.

In selling the Sun-Times in 1986, Murdoch freed Ann Landers from her contract and she too — her real name was Eppie Lederer — came “across the street,” prompting Squires to say how pleased he was “to welcome Ann Landers to the finest lineup of journalism talent anywhere.” He was onto something because it can be argued that in the history of Chicago journalism, no two columnists were as popular as Mike and Eppie.

They liked one another. Royko told me at the time, “I’m glad she’s here. Now, all those wackos who’ve been writing to me with their problems can write to her.”

There were still people writing letters, of course, but many were being sent electronically as the world and this newspaper moved into the digital age. Early on, typewriters (and their glorious noise) were replaced by computers in newsrooms and in 1991 the newspaper company bought a 9% share of America Online. It would offer full text of the Tribune on AOL in 1993, and in 1995 the newspaper offered its first breaking news coverage on the web after a suburban Fox River Grove train and school bus crash.

The paper would expand its suburban bureaus and start CLTV, a 24-hour cable news operation. It had the Cubs, of course, the team and its field purchased from the Wrigley family for the bargain price of $21.1 million. After a lengthy battle with homeowners, night games started in 1988.

As the newspaper fixed its eyes firmly on the future, it got rid of a beloved remnant of its past. It was “Injun Summer,” an illustration by John T. McCutcheon, who had joined the newspaper in 1903. It first appeared on Sept. 30, 1907, and became so popular that it was reprinted every autumn. By the 1990s, Tribune editors decided to end the annual tradition, announcing that the illustration was “out of joint with its times. It is literally a museum piece, a relic of another age.”

Thousands called to complain and the paper, and life, moved on.

The paper mourned the death of Royko, whose last column on March 21, 1997, was about his beloved Cubs. He died the next month, missing the celebration of the paper’s 150th birthday later in the year, which included these words: “The Tribune is a very healthy business in a city whose history is littered with the bones of great newspapers that have failed. It has been most astute at this elemental responsibility, evolving from newspaper to media empire, moving aggressively into whole new worlds of media competition.

“You can find the Tribune on city street corners, suburban doorsteps, on television, on your radio, and on computer screens.” It wouldn’t be long until another medium would be added to that list: the ever-present smartphone.

Eppie Lederer would continue to write Ann Landers into the new century, which would be shadowed and altered and driven by the “wonders” of the internet.

Eppie never jumped in. She continued to write her columns on an electric typewriter, telling me long ago, “I know it would be easier if I got into the computer age. Just call me old-fashioned.”