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Sammy Sosa & Donald Trump (& Hillary Clinton): A History

"Through more recent friendships with Puffy Combs, Sammy Sosa and others, I've had the chance to learn firsthand about the diversity of American culture." - Donald Trump in his book The America We Deserve


This passage is getting quoted a lot these days in light of Trump's racist statements on the campaign trail. I thought I'd document the public record on Trump's friendship with Sosa.

December 10, 1998, Tribune:

"One night after hitting the Playboy Mansion in Los Angeles, jet- setting Sammy Sosa was in New York, having dinner with Donald Trump, who said, 'Sammy told me he thinks he can equal or surpass what he did last year.'"


May 26, 1999, Sun-Times:

"Asked if he has developed a strong friendship with any celebrity since emerging last year as a nationally renowned figure, Sosa didn't hesitate.

"'Yeah, Donald Trump,' he said. 'I didn't know him before. He treats me nice. He wanted to meet me. He called my people, and we got together. He's a good guy.'"


May 28, 1999, Sun-Times:

"It's friendship with Trump, not business," [Sosa's personal manager Domingo] Dauhajre said. "He called and said: 'Domingo, tell Sammy to have a good day and a good season and that I'll keep in touch. I don't want to bother him.'"


July 10, 1999, Sun-Times, Jay Mariotti:

"The president fawns over him. Donald Trump does martini bars with him. He's the reigning giant of slugging, fan balloting and sporting celebrity."


July 24, 1999:

PHOTO: "Baseball star Sammy Sosa, Donald Trump and girlfriend Melania Knauss attend surprise 30th Birthday Party for Jennifer Lopez at Halo, NYC."


September 7, 1999, Sun-Times, Jay Mariotti:

"Does Sosa act like a star? Yeah, sure. But I've seen athletes with far fewer feats act much more obnoxiously. He does back up his swagger with his swing. Clearly, he soaks up the attention and loves his newfound celebrity: his relationship with the Clintons, his friendship with Donald Trump, his appearance at Jennifer Lopez's birthday party, his invitation to Michael Jackson's house (yikes) when the Cubs were in L.A., partying with Charlie Sheen and Hugh Hefner, handshakes with Arnold and Denzel and Sly."


Sept 20, 1999, Tribune:

"Sosa spent a relaxing night at home with his family Saturday after hitting No. 60, watching Felix Trinidad defeat Oscar De La Hoya in the pay-per-view welterweight championship fight.

"He received some calls of congratulations. Donald Trump gave a holler. The president of the Dominican Republic called too."


Oct. 27, 1999, Tribune:

"Invitations to Sammy Sosa's birthday bash next month have gone out to Hillary Clinton, Donald Trump, Rev. Jesse Jackson and the president of the Dominican Republic."


November 15, 1999, Sun-Times:

"There was plenty of clout at Sammy Sosa's birthday bash. Politicians and celebrities joined the Cubs slugger Friday at his home in the Dominican Republic as he turned 31.

"'We confirm this is the party of the century,' Sosa said.

"Among the crowd, which included non-celebrity Dominicans, were the Rev. Jesse Jackson Sr., millionaire Donald Trump, Cuban salsa star Celiz Cruz, Mexican singer Ana Barbara, actor James Edward Olmos and musician Kenny G.

"Political figures included Dominican president Leonel Fernandez, former Spanish president Felipe Gonzalez and former Colombian president Belisario Betancourt. Baseball players Pedro Martinez, Alex Rodriguez, Jose Rijo and Glenallen Hill attended."


June 29, 2000, Sun-Times:

"If [I get traded to] the Big Apple, I will be happy," he said. "There are a lot of Dominicans there. I have a lot of friends there, Donald Trump and Hillary Clinton. If I do go there, it will be great being around a lot of great players. I don't have to be the man every day."


July 5, 2000, Tribune:

"Sammy Sosa called reporters to his dressing cubicle before Tuesday's game. A score of media types crowded around him, wondering if Sosa was going to rip Cubs management, make up with management or announce where he wanted to be traded.

"Instead, Sosa invited reporters to his 32nd birthday party Nov. 12 at his home in the Dominican Republic.

"'I'm inviting a list of celebrities like Donald Trump and Rev. Jesse Jackson,' Sosa said. 'You're on my list, too. I'm inviting every one of you.'

"It was Sosa's attempt to lighten the atmosphere around the Cubs, which has grown occasionally contentious amid continuous trade rumors and poor play."


July 10, 2000, Tribune:

"Donald Trump got the Wrigley experience Sunday . . . Trump needed the lyrics to 'Take Me Out to the Ball Game' written down in the booth before he could sing."


July 10, 2000, Sun-Times column by Carol Slezak:

"The Donald was at Wrigley Field on Sunday. (That's Mr. Billionaire himself, Donald Trump.) And the crowd booed him lustily when he threw out the first pitch. It booed him more lustily when he sang (admittedly, a bit off key) during the seventh-inning stretch.

"What did The Donald ever do to Chicago, anyway? Imagine that, booing a guest of Sammy Sosa's in Sammy's house. Harrumph.

"That's right, The Donald and his girlfriend, Melania Knauss, a model from Austria, were Sosa's guests. And The Donald, a big sports fan, was loving every minute of his first visit to Wrigley Field.

"'It's every bit as good as I've heard it was,' he said.

"If you've never seen The Donald in person, let me help: He looks exactly how he looks on television. From his reddish hair, sprayed to withstand New Orleans-style humidity, to his bewitching red eyebrows, to his navy blue suit and pink tie, he was The Donald.

"As for his young model-girlfriend, well, I can tell you this much: The male-dominated press box was all adrool over Ms. Knauss. To paraphrase what my male colleagues said, she's hot. (On their behalf, I'd like to add that they also believe Ms. Knauss to be very intelligent. As I said, I'd like to add that, but not one of the dunderheads ever mentioned it.)

"Anyway, I'm wondering why The Donald was booed. He seemed like a great guy to me. Honestly. And think of everything he's accomplished in his life. This guy is a winner.

"In the 1970s he saved New York City from bankruptcy. I think he did this by building, buying and selling tall buildings, but I suspect that's too simplistic of an explanation. In any event, it was a modern miracle.

"In the '80s he owned the USFL's New Jersey Generals. He knew talent - his players included Herschel Walker and Doug Flutie. And he wasn't a cheapskate. His spending actually helped cause the USFL's demise, because none of the other franchises could keep up with him. He wanted an NFL franchise, but the NFL owners shut him out. They were afraid of him, I think.

"He also has provided us with many fun, what's-he-doing-this-time moments. There was his book, The Art of the Deal. There was his recent, brief, failed presidential candidacy (here he gets points for trying). And then there are the women. Ivana, Marla, Ivana and Marla, Ivana and Marla fighting. And since then, a succession of others.

"And now he's buying and building casinos on land and on water (including one in East Chicago), and I'm sure he's making mo' money, mo' money, mo' money.

"Before the Cubs-Sox game, I watched The Donald work the Cubs' locker room. He's a smoothie, I'll tell you that. He seemed as at home in a locker room as he must be in a board room. He hugged his good pal, Sammy. They chatted each other up for several minutes while Ms. Knauss stood off to the side, with two men who appeared to be bodyguards standing near her. (I was unable to determine whether they were shielding her from the Cubs players or from my colleagues, but I assume it's the latter.)

"The Donald went to leave, but not before he gave the Cubs a pep talk.

"'I didn't come all this way to see you lose,' The Donald said. 'Win!'

"Then he turned to Cubs starter Kevin Tapani.

"'Win!' he said to Tapani.

"Tapani, a bemused look on his face, looked at The Donald as if to say, 'Who is this guy and why is he yelling at me?'

"'I don't know him,' Tapani said after the game. 'I didn't think he was talking to me. I guess he's a big baseball fan.'

"Ah, yes, baseball. The Donald loves baseball.

"And get this: He loves the Cubs.

"'I used to watch Don Baylor play,' The Donald said.

"'The Cubs have had some tough luck with injuries this year, like Kerry Wood,' The Donald said.

"Why was The Donald booed to smithereens at Wrigley? That was a big mistake. He should have been applauded. He should have received a standing ovation. Imagine, Cubs fans, an owner like The Donald.

"After The Donald sang (OK, very off-key, bordering on Mike Ditka-like off-key) during the seventh-inning stretch, he was asked what kind of owner he'd be. Hypothetically speaking, of course.

"'Oh, I would try to win,' he said. (Competitive; excellent response.)

"And how would he go about that?

"'The first thing I'd do if I owned the Cubs was sign another couple of Sosas,' The Donald said. (Big spender; excellent sign.)

"So in other words, he'd be the exact opposite kind of owner than, say, Tribune Co.?

"The loquacious Donald went silent. Behind his bewitching eyebrows, his brain waves seemed to be twitching. He was thinking, hard and quick.

"'(The Cubs) are my hosts,' he said. 'I'm not going (to criticize the organization).'

"Oh, but he wanted to. Because for The Donald, only one thing matters. Winning. Just ask his friend Sammy.

"'He's so competitive,' Sosa said. 'I'd love to see him go out and buy a team.'

"And have we got the team for him."


PHOTO: Donald Trump throws out the first pitch to Sammy Sosa.


July 4 2001, Tribune:

"Some athletes try to block out the extra attention that comes with playing before an enormous, star-studded crowd.

"Sammy Sosa thrives on the attention.

"A day after he dined with Donald Trump and Trump's girlfriend, Melania Knauss, at a chic Italian restaurant in Manhattan, Sosa thrilled a Shea Stadium crowd of 52,471 Tuesday night with two of the Cubs' six hits, including a home run, in a 3-0 victory over the Mets."


June 11, 2003, Tribune, post-corked bat:

"Sosa said he's encouraged by hearing from so many supporters, including former President Bill Clinton, Donald Trump and Dominican President Leonel Fernandez. He said Clinton told him to 'stay strong.'"


Nov. 12, 2003, Tribune:

"Yes, it's that time of year again. Sammy Sosa's birthday party that is. Sosa will celebrate his 35th on Saturday, Nov. 22 with a few thousand of his closest friends in the Dominican Republic. Bud Selig will be there and will present Sosa with a special award recognizing him as the first Latin player to hit 500 home runs. Among other celebrities expected to attend are Donald Trump, actor John Cusack, Cubs President and CEO Andy MacPhail and other Latin American personalities.


April 16, 2004, Sun-Times:

"Donald Trump and Sammy Sosa are close friends, so it was no surprise that Trump called and left Sosa a good-luck message before the season began. Sosa is a fan of The Apprentice, the hit TV show that concluded Thursday night, and enjoys telling Trump 'You're fired,' when they talk on the phone."


February 28, 2016:


"Sammy Sosa is orchestrating a Clinton vs. Trump election because that will give him the power over the United States government."


May 6, 2016: Sammy at a Hillary event.


Comments welcome.

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