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The best Hillary Clinton and Donald Trump anecdotes from the SI Vault

Before they ran for president, Hillary Clinton and Donald Trump appeared often in the pages of Sports Illustrated. 

Sports Illustrated has been around for the entirety of Donald Trump and Hillary Clinton’s adult lives, and as massive public figures they’ve appeared in its pages on dozens of occasions. 

With Election Day finally here, we dug through the SI Vault to find the best anecdotes about each candidate, from Hillary’s flip-flopping on her baseball rooting interests, to Trump’s misadventures in the USFL. 

(Click on the dates to read the full story.)

Hillary Clinton

May 17, 1993 — A mule named Hillary Clinton is great at polo

Garon Stutzman of Clifton, Va., rides his thoroughbred mule, Hillary Clinton, in the Bull Run Hunt Club's fox hunt and the Howard County Iron Bridge Hunt in Virginia. In fact, Stutzman is the whipper-in of the hunt, the man who keeps the hounds together. He says Hillary is perfect as a whipper-in mount because she has tremendous stamina and is not afraid of the sound of a whip or a pistol. She jumps anything, including barbed wire and fallen trees, and her thick hide makes it easier for her to crash through brambles. "She may not be as fast as the horses, but she's a doggone good animal for this sport," he says.

Sept. 12, 1992 — Andy Van Slyke doesn’t like Hillary

Hillary Clinton, for one, really bakes his cookies. "My wife has done more for this country than Hillary Clinton ever did," says Van Slyke. "It is great security for a child to come home from school and know that his mother will be there. Good mothers are underrated, just like good defense."

March 7, 2007 — Hillary is a flip-flopper

Does the former First Lady see both sides of an issue? Or can't she commit? You decide. During the 2000 New York Senate campaign Clinton told Katie Couric she had "always been a Yankees fan." That was news to Chicagoans, who had seen her throw the first pitch at a Cubs game in '94 and sport a cap signed by Sammy Sosa in '98. Asked in 2003 whom she'd root for in a Cubs-Yanks series, she said, "It's like a no-hit game, you don't talk about it."

June 10, 2003 — LPGA Hall of Famer has a new haircut

Hall of Famer Betsy King, 47, has picked up a Pilates trainer, shed 15 pounds and ditched her trademark Hillary Clinton hair helmet in favor of straightened, dyed-blonde locks that have earned her rave reviews for a more stylish look.

Feb. 21, 1994 — Hillary loves Olympic skiier Tommy Moe

With his elfin smile and his undisguised elation over his victory, Moe captured the hearts of the 30,000-plus spectators who gathered in 5° sunshine at the downhill course in Kvitfjell, 35 miles north of Lillehammer—among them Norway's King Harald V and Queen Sonja, and Hillary Rodham Clinton. The First Lady arrived after Moe had completed his run, but she greeted him with congratulations and later mentioned that she had once spent a pleasant college summer working in a cannery in Alaska.

Jan. 11, 1993 — Olympian Kristen Babb-Sprague wonders what Hillary would think

Kristen is now retired. She mostly wants to be a ballplayer's wife, though she does a consumer report once a week on local TV. She laughs and says she would not mind being Martha Stewart, the arbiter of suburban decorating trends. What could be better? Stay at home and entertain and be paid. Kristen says that "Hillary Clinton would probably slap me upside the head for saying this," but she is ready to be domestic.

Oct. 11, 2004 — Hillary’s life lessons about the Cubs

The Cubs were going to the World Series, something no one under the age of 58 had ever witnessed, including Hillary Clinton, who once said, "Being a Cubs fan prepares you for life--and Washington."

Feb. 9, 1995 — Grant Hill’s mom roomed with Hillary in college

Mom shared a dorm suite with Hillary Rodham Clinton at Wellesley, and Dad was a flatteringly rendered character in the original Doonesbury while at Yale, so you could say Grant is the progeny of the cultural elite too.

Feb. 25, 2003 — Swimsuit model Daniela Pestova wants to see Hillary in body paint

The celebrity she most wants to see body-painted "Hillary Clinton." It's not likely that the junior senator from New York will be appearing in the Swimsuit Issue anytime soon, but Pestova has graced these pages seven times; she has been on the cover twice (1995 and 2000).

March 6, 1996 — Figure skating coach’s clever euphemism

What's so bad about Suzanne Bonaly? Carlo Fassi, the coach who guided Peggy Fleming and Dorothy Hamill to Olympic gold, grins and replies, “You remember what Newt Gingrich's mother said about Hillary Clinton, don't you?”

(This is what she said, if you need to jog your memory.)

July 28, 2008 — Hillary’s bodyguard went to the Olympics

Judoka Adler Volmar, a onetime Navy medic, served as a bodyguard last year in the presidential campaign of Hillary Clinton. When Volmar was growing up in Haiti his father worked briefly as a driver for that country's then dictator, François Duvalier.

Donald Trump

Aug. 23, 2004 — Trump has a bunch of takes

• HERB KOHLER We talked a lot about fixtures--his favorite subject.

• KOBE BRYANT I hope that he's exonerated and sues the girl for damages.

• JAMES MCgreevey Very sad. Hopefully he'll be happy now.

• TERRELL OWENS He's no Jerry Rice. He's fooling himself if he thinks he is.

• ELI MANNING OR KURT WARNER They didn't pay Manning all that money to put him on the bench.

• DREAM TEAM We're not sending our best players.

• MICHAEL PHELPS He'll win eight medals--six gold.

• PETE DYE He's one of the best, and the architect of my course in California.

 April 15, 2002 — The Brady-Trump romance begins

"The kid has great self-confidence and an unbelievable personality, and he's got the maturity of a much older man," Trump said later. "Let me tell you, if one thing stands out about Tom Brady, it's that he loves those women. And, guess what? They love him too."

March 14, 1988 — Trump flirts with buying the Patriots

For instance, on Feb. 16, Murray and the Sullivans announced that real estate mogul Donald Trump wanted to buy the team in an arrangement that would have given the Sullivans millions of dollars and allowed Murray to retain a stake in the Patriots. Trump met several times with the two sides to discuss a deal. However, on Feb. 29, Trump said he was no longer interested in acquiring the Patriots or in helping the Sullivans find a buyer. Chuck says Trump's fear was that the NFL would try to block his efforts to buy the team. "He said he had no problems with the numbers," says Chuck, "but was more concerned about having the league shun him." 

May 22, 1989 — The Tour de Trump

If you could get past the name, the Tour de Trump, without losing your lunch, and if you could somehow divorce the sporting event from the excess baggage that went with it—the Trump Princess, the Trump Plaza Hotel and Casino, the chest-Trumping cameos of King Donald himself, whose ideas for improving the Tour de Trump included adding a few laps around the White House and continuing the race to Los Angeles via Detroit, Chicago and San Francisco—what you had was a pretty nice bicycle race.​

Jan. 5, 1987 — America’s Cup captain wants Trump to sponsor him

I called on Donald Trump and asked him for $3 million. I told him we'd name the boat Trump Card. He gave it a lot of thought.

May 31, 1993 — Trump tries to lure Steve Young to the USFL

That weekend [in 1984] he received calls from NFL commissioner Pete Rozelle and former Dallas Cowboy quarterback Roger Staubach telling him to sign with the NFL. Donald Trump, who owned the New Jersey Generals in the USFL, and Howard Cosell urged him to try the USFL. Young began to feel tremendous pressure. The prospect of being rich didn't make him happy. 

March 12, 1984 — L.A. Express owner J. William Oldenburg calls out Trump

"You can write this down," he said. "With or without Steve Young, the L.A. Express will be the professional team. Not just in the USFL, but in the USFL and the NFL. I'm used to winning, to nothing less than becoming the best. Donald Trump [owner of the New Jersey Generals] can get all the press he wants, but when it comes to business he can't carry my socks."

Feb. 13, 2006 — Trump roasts Don King

"HEY, FREDDIE, how come HE has to SIT so NEAR ME? Move OVER, DON.... You know he KILLED PEOPLE? This guy KILLED PEOPLE. I'm going to say things about him, and I DON'T WANT TO BE KILLED...." He waits, maybe for comic effect, maybe to let the echo fade. "How come there are so FEW BOXERS HERE? Because DON KING has SCREWED so many BOXERS, nobody WANTS TO COME!" 

July 7, 1986 — Trump hastens the downfall of the USFL

In a 1984 letter to Taube, Myles Tannenbaum, managing general partner of the USFL Philadelphia Stars, wrote of Trump, "Donald wants to move the league into the fall so that a merger with the NFL could be forced—he told me that in so many words on two occasions." 

Nov. 13, 1989 — Indiana track star Bob Kennedy admires Trump

A business major with a GPA of 3.0, Kennedy is nothing if not a pragmatist. He is interested in a career in corporate law, and his summer reading included Donald Trump's The Art of the Deal. "I like the way Trump gets things done," says Kennedy.

Nov. 7, 1988 — Boxing promoter Bill Cayton and Trump have beef

Cayton's troubles began when [Mike] Tyson married Givens. "She and her mother [Ruth Roper] poisoned his mind against me," Cayton has said. At Roper's insistence, and with Donald Trump chiming in as Tyson's much-ballyhooed (mostly by Trump himself) "adviser," Cayton agreed to have his share of Tyson's purses reduced from one third, the going rate for boxing managers, to 20%, and his take of the champion's outside endorsements cut even more drastically. Trump claimed last week that Tyson owes him $2 million, to be paid to charity, for helping to rework the contract with Cayton.  

Sept. 13, 1999 — Trump is a tennis agent

Befitting a man whose threshold for shame is so high that he names skyscrapers in his honor, Donald Trump issued a press release last week to announce that he was in the tennis agent business, never mind that his lone client has yet to play a pro match. T Management Group, as Trump's agency is called, will represent Monique Viele, a 14-year-old prodigy who had been with IMG since she was nine and her parents sent the omnipotent management firm a videotape of her whacking balls.

Feb. 4, 1985 — Trump courts Doug Flutie for the USFL

Trump had been coveting Flutie for a long time, and courting him for the last month.

"I think he's really excellent," Trump says. "He's going to be great for the league. I love the concept of having him in the same backfield as Herschel Walker. It opens things up tremendously. They won't be able to just key on Herschel. I've never seen a reaction like this. This is bigger than the Herschel deal."

Two weeks ago Woolf and Flutie met with Trump at his headquarters in New York City's Trump Tower. At one point Flutie was taken to a private theater and shown a five-minute film entitled Trump Tower, A World of Glamour. "That's pretty much the big time to me," said Flutie. Trump had originally planned to take Woolf and Flutie to lunch, but then realized they might draw too much attention. So he had sandwiches brought up. Flutie had the turkey.

"I was struck by Mr. Trump's enthusiasm," said Flutie. "I didn't know what to expect from him. But he was very easy for me to talk to—of course, he did most of the talking."

June 8, 1998 — Trump gets a byline

I don't buy the idea that golf is too expensive. You may say it's outrageous to pay $300 to play Pebble Beach, but I say it's cheap. Where else can you get a piece of heaven for a price like that?

Aug. 18, 1986 — Trump officially sinks the USFL

​When the USFL's owners met in New York Aug. 4 to determine the league's future, six wanted to play this fall. Stephen Ross of the Baltimore Stars and Donald Trump of the New Jersey Generals did not. ''I believed as late as (the night before) that we would play,'' said Lee Scarfone of the Tampa Bay Bandits. ''We voted by teams alphabetically. When Donald Trump voted no, that was it. The ESPN television contract required that there be a New York area team.When he said no, it didn't matter how the rest voted.'' Trump saidhis main objective now was to pursue further legal means of attempting to win hefty damages from the NFL. ''I am not interested in owning an NFL franchise,'' he said. ''I am looking for a victory in court.'' 

June 15, 1992 — Trump is tight with the “Let’s get ready to rumble” guy

[Michael] Buffer is moving in heady circles these days, hanging with celebrities. The Buff, as he is sometimes known, is good friends with the Donald. Trump likes Buffer's style and uses him for all his Atlantic City fight cards. "He's great, he's the choice, he has a unique ability," says Trump. "I told my people, 'We got to have him.' " During the action Buffer often sits ringside with Trump, and with Trump's fiancèe, Maria Maples, who is a big Michael Buffer fan. "Michael has real professionalism," Maples says. "He makes people feel good and credible. Also, he has the warmest, nicest eyes." 

Dec. 17, 1990 — One of Trump’s classmate’s is a pretty good businessman

If Donald Trump continues having trouble making interest payments on the Taj Mahal, maybe he should call up Paul Schmookler, one of his old schoolmates from New York Military Academy, for some moneymaking tips. Schmookler, 43, is positively thriving in Millis, Mass., selling vintage fishing tackle, angling art and, in particular, flies. 

July 21, 1986 — Jim Kelly and Trump have lofty expectations for the USFL

"I'd like to play for the Raiders. I'd like to live in California," Kelly says. "But what I'd really like to do is play for the New Jersey Generals and Donald Trump and merge with the NFL and take the run-and-shoot with Herschel Walker in the backfield and just kick ass."

"If we win, we will have more money than the NFL, and that will be interesting," says Trump. "We already have teams that would beat most NFL teams."

May 25, 1992 — A spooky anagram

The Tour Du Pont's organizers must be equally glad to have LeMond's name on their list. This year marked the fourth edition of the race, which bills itself as "America's Premier Cycling Event." In its first two years the race was known as the Tour de Trump, but The Donald is long gone, and with Du Pont having stepped in as the main sponsor last year, the race has taken on new stature. May's Tour Du Pont (an anagram, by the way, for "Not you, sad Trump") is now a fixture on the international cycling calendar. 

Nov. 22, 1999 — We shouldn’t have joked

[Peter] Warrick isn't just good, he's scary good. He is 6 feet, 195 pounds and runs like a dot of mercury on a marble countertop. "He starts, stops and then starts up again in another direction, and it's like he never stopped in the first place," says Georgia Tech safety Travares Tillman. According to the stopwatch Warrick runs a relatively pedestrian 4.45 seconds for the 40-yard dash, which is a bigger joke than Donald Trump's running for president.