CHICAGO (CBS Chicago/CBS News) — Former Gov. Rod Blagojevich and President Donald Trump have a history going back many years – to a time well before Blagojevich went to prison and before Trump was best known as a politician.

President Trump announced Tuesday afternoon that he was commuting Blagojevich’s 14-year prison sentence, which would free the former governor from prison without clearing his criminal record.

As CBS 2 Investigator Megan Hickey reported Tuesday evening, President Trump has repeatedly said he and Blagojevich are not friends. On Tuesday, he again told reporters at Joint Base Andrews, “He seems like a very nice person, don’t know him.” But they do, in fact, have connections that can be traced back nearly two decades

Blagojevich was arrested at his home in December 2008, on charges accusing him of seeking to personally benefit from his position as governor; including trying to sell an appointment to the U.S. Senate seat once held by Barack Obama before he was elected president in 2008. After two trials, he was convicted of more than a dozen corruption counts and sentenced to 14 years in prison. He has been behind bars since March 2012.

RELATED: The Blagojevich Saga: How Did We Get Here?

In the three years and four months between his arrest and the day he reported to prison, Blagojevich became something of a pop-culture celebrity. Among his projects was an appearance on Trump’s “Celebrity Apprentice” show in March and April 2010.

Blagojevich was “fired” by Trump on April 4, 2010, after four weeks on the show.

Trump “fired” Blagojevich after his team slipped up in creating a 3-D promotional experience for Universal Studio’s new “The Wizarding World of Harry Potter.” Team leaders – Blagojevich and Victoria’s Secret model Selita Ebanks – were flown to Orlando to meet with theme park executives, while their teams back in New York began worked on the project.

Blagojevich’s men’s team lost the challenge, primarily because of faulty research. Their details were not authentically “Harry Potter,” something which theme park execs took pride in. Blagojevich, who mispronounced some of terms, was blamed for not assigning someone to do the research.

Making an appearance for the season finale the following month, Blagojevich told Trump he was grateful for the opportunity to tell the public himself that he was innocent of the charges against him. He again profusely expressed his innocence.

Trump at the time went on to ask the other assembled contestants from that season, “Who thinks Rod is guilty?”

Met by silence, Trump persisted. Finally, Olympic sprinter and TV commentator Michael Johnson sheepishly raised his hand, shrugged and then leaned back and shook hands with Blagojevich, who was seated behind him.

On April 2, 2011, Blagojevich uttered some flattering words about Trump as he spoke to high-schoolers attending the Junior Statesmen of America convention in Oak Brook that politics needs them.

“Look, I’ve been fired before,” Blagojevich said, drawing mild laughter from the crowd that day. “But he’s the only guy who’s fired me whom I really like. I think he has a tremendous amount to offer. He’s not a politician. He’s a man who’s hugely successful, a billionaire probably many times over, who’s also had his share of adversity.”

Despite their belonging to opposite political parties, Blagojevich said he would be “rooting” for Trump.

It was around that time that Trump was beginning to draw attention in the political sphere. Also in April 2011, Trump called upon President Obama to release his long-form birth certificate amid “birther” theories that claimed Obama was not born in the U.S. – and took credit when Obama did so, despite Obama dismissing it as a distraction by “sideshows and carnival barkers.”

Amid that controversy, Trump was considered a potential 2012 Republican presidential contender and said he thought he would beat Obama – though he ultimately decided not to run and endorsed Republican Mitt Romney.

And dating back even before Blagojevich’s stint on “The Celebrity Apprentice,” Trump and Blagojevich had a relationship that involved Trump’s checkbook.

Trump personally donated $7,000 to Blagojevich’s campaigns ($5,000 in 2002 and $2,000 in 2007) before his conviction, and his hotel and casino organization donated another $2,000 in 2003. The records do not show any donations to Blagojevich’s Republican opponents – Jim Ryan in 2002 or Judy Baar Topinka in 2006.

Blagojevich even mentioned Trump just as he was preparing to report to federal prison in March 2012.

“I got fired by Donald Trump,” Blagojevich said at the time. “This thing I’ve got to do now is worse.”

Once Trump took office in January 2017, Blagojevich had been in prison for nearly five years. And since he took office Trump has repeatedly has suggested Blagojevich’s 14-year sentence was too severe for his crimes.

President Trump said in May 2018 that he was seriously considering commuting Blagojevich’s sentence.

The subject came up again in August of last year. On Wednesday, Aug. 7, President Trump said on Air Force One: “I am thinking very seriously about commuting his sentence so that he can go home to his family after seven years. You have drug dealers that get not even 30 days, and they’ve killed 25 people.”

But the very next day, Trump’s tone had changed. He tweeted that the White House staff was “continuing the review of this matter” when it came to what to do with Blagojevich’s sentence.

On Tuesday, President Trump made good on his remarks.

“He served eight years in jail, has a long time to go. Many people disagree with the sentence,” Trump said before boarding Air Force One to head to California on Tuesday. “He’ll be able to go home with his family after serving eight years in jail. That was a tremendously powerful, ridiculous sentence in my opinion, and in the opinion of many others.”

It’s unclear exactly when Blagojevich would be released from the federal prison in Colorado where he is incarcerated.

CBS Chicago web producer Adam Harrington contributed to this report.

Megan Hickey