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Trump's big political "surprises": A history

New York developer and potential Reform Party presidential candidate Donald Trump and Minnesota Governor Jesse Ventura take questions at a news conference after Trump gave a speech at a Chamber of Commerce luncheon, Jan. 7, 2000 in Brooklyn Park, Minnesota, the city where Ventura was once mayor. Craig Lassig/AFP/Getty Images

Flirts with a 2000 presidential run

Donald Trump briefly tested the waters for a presidential run in 1988, but it wasn't until 1999 when the Trump self-promotion machine went into full force. 

Fresh off his divorce from Marla Maples, flaunting his new girlfriend (and now-wife) Melania Knauss, and promoting a new book that laid out his political views, Trump sensed a possible political opening.  The Reform Party, the party created by Ross Perot after his 1992 presidential run and the vehicle for his 1996 run, was set to receive federal funding in 2000 after Perot received eight percent of the vote in 1996.  Trump started talking up a possible Reform Party bid, pitting him against famous conservative Pat Buchanan.

In his book, "The America We Deserve", he proposed a one-time 14.25 percent tax on those worth more than $10 million (he was on that list) and suggested the country could use a wily businessman like him as president.

"The dealmaker is cunning, secretive, focused and never settles for less than he wants," Trump wrote. "It's been a long time since America had a president like that."

And, perhaps leaving some wiggle room in case he didn't follow through with his presidential flirtation, Trump added, "Do I need to be president to feel good about myself? I feel pretty good right now." 

Trump's big political "surprises": A history

Donald Trump and Melania Knauss at the Aida opening in New York City, NY on March 23, 2000 Scott Gries/Getty Images

Flirts with a 2000 presidential run

In Feburary of 2000, he decided not to run after all, citing infighting within the Reform Party.

"[T]he prospect of divisive lawsuits, continued fighting over the national convention site and general fratricide" would doom the ultimate nominee of the party, Trump said. 

He was right: the party wound up splitting into two, having two conventions, nominating two candidates - Buchanan and John Hagelin - and fought over the federal funds that were due to the party's nominee.  And, it turned out, Ralph Nader had more of an impact on the outcome of the 2000 election than either of the Reform Party nominees.

Trump's big political "surprises": A history

Donald Trump talks to the press after receiving the American Automobile Association's (AAA) Five-Diamond Award for Trump's International Hotel & Tower New York at the hotel on March 31, 2011. Timothy A. Clary/AFP/Getty Images

Calls for President Obama's birth certificate

While most Republicans in 2011 were busy questioning the president's leadership or his agenda, Trump employed more controversial tactics to undermine Mr. Obama. As the business mogul ginned up speculation about yet another presidential bid, he revived the conservative conspiracy theory that Mr. Obama was born outside of the United States.

Questions about Mr. Obama's origins plagued his 2008 campaign, but he put them to rest temporarily by releasing his birth certificate. The controversy exploded once again in the spring of 2011 because of Trump.

"The reason I have a little doubt -- just a little -- is because he grew up and nobody knew him," Trump said in an interview with ABC's "Good Morning America" that aired March 17. "If I got the nomination, if I ever decide to run, you may go back and interview people from my kindergarten. They'll remember me."

Trump's big political "surprises": A history

Calls for President Obama's birth certificate

Trump managed to win so much media attention by questioning Mr. Obama's origins that he finally compelled the White House to respond. In one of the more surreal moments of the Obama presidency, the White House on April 27, 2011 released copies of President Obama's long-form birth certificate to quell rumors that the president was born outside of the United States. Mr. Obama even made an impromptu appearance in the White House briefing room to urge the press and American citizens to drop the issue and focus on the nation's real problems.

"We're not going to be able to solve our problems if we get distracted by sideshows and carnival barkers," Mr. Obama said. "We've got some enormous challenges out there. There are a lot of folks out there still looking for work... We do not have time for this kind of silliness."

Meantime, Trump held a press conference to talk about how "proud" he was to force the birth certificate issue.

"I am really honored frankly to have played such a big role in hopefully, hopefully, getting rid of this issue," he said. "We have to look at it, we have to see is it real, is it proper, what's on it, but I hope it checks out beautifully," Trump said.

Trump's big political "surprises": A history

Flirts with a 2012 presidential run

As he did previously in 1988 and 2000, Trump again flirted with running for president, first as a Republican, then, as time passed and it became clear he wasn't going to enter the GOP primaries, as an independent. 

During the height of the Republican primary season in January, he told CBS' Bob Schieffer on "Face the Nation" that he thought the GOP was hurting itself with the level of "hatred" the presidential candidates were throwing at each other.

As for an independent run, he told Schieffer, as he did in his 2000 book, "The America We Deserve", running for president is not something he necessarily yearns for, despite all of his bluster.

"It's not something I want to do, I'd love to see a candidate come along who's going to go up but if I don't see a person that, number one, is going to win, that's tantamount, I would certainly think about doing it after the show ends," Trump told Schieffer.

Alas, Trump's run never came to fruition and he ultimately endorsed Mitt Romney.

Trump's big political "surprises": A history

Donald Trump speaks at the Ritz-Carlton on August 26, 2012 in Sarasota, Fla. Trump accepted the Statesman of the Year Award at the Sarasota GOP dinner ahead of the Republican National Convention in Tampa. Edward Linsmier/Getty Images
Promises a "surprise" at GOP convention

Ahead of the Republican National Convention in August, rumors circulated that Trump would take some part in the event, at which Mitt Romney officially accepted the Republican presidential nomination.

Trump himself, of course, hyped up his presence: "I was asked to speak at the RNC but said no, because I will be doing something much bigger - just watch!" Trump wrote on Twitter. Trump spokesman Michael Cohen told CBS News that his boss would play "a huge, huge role" that will "certainly be memorable for the convention-goers."

Thanks to Hurricane Isaac, Trump's "huge role" at the Tampa convention never materialized and he wound up receiving an award from the Sarasota (Fla.) Republican Party instead.

Trump's big political "surprises": A history

Donald Trump speaks during a press conference following his address to the Scottish Parliament on April 25, 20012 in Edinburgh, Scotland. Photo by Jeff J Mitchell/Getty Images

Latest "big surprise" due out Wednesday

In his latest tease, Trump told Fox News this month that he has a "big announcement" pertaining to President Obama that could "possibly" impact the election.

"I have something very, very big concerning the president of the United States," he said. "It's very big, bigger than anybody would know." He refused to give any further details, simply adding, "I know you will cover it in a very big fashion."

Stay tuned?