QB Doug Flutie speaks at a news conference in 1985 after signing a multi-year contract with Trump's New Jersey Generals USFL franchise. Flutie started immediately and helped lead the team to an 11-7 record in his rookie season.
2 of 25AP
Dennis Conner, captain of America's Cup champion "Stars and Stripes," receives a model of his winning yacht from Trump during a reception in February 1987. Trump was one of Conner's financial backers; he even paid for a victory parade in New York.
3 of 25AP
Yankees manager Billy Martin jogs out to meet Trump and his son Donald, who are seated with Yankees owner George Steinbrenner during a spring training game against the Expos in 1988. New York finished fifth in the AL East that season.
4 of 25AP
Trump looks on as boxing promoter Don King holds up the wrists of heavyweight champion Mike Tyson and challenger Larry Holmes in 1987. Less than two months later, Tyson knocked out Holmes in the fourth round.
5 of 25 Ron Galella, Ltd./WireImage
Ivanka Trump and her father take in a game in 1991.
6 of 25Ron Galella/WireImage
Trump with tennis star Monica Seles and actress Marla Maples in July 1991. Seles won three majors (Australian, French and U.S. Opens) in 1991 but was unable to compete at Wimbledon because of shin splints.
7 of 25AP
Boxers George Foreman and Shannon Briggs hold Trump's arms during a news conference. Briggs won a controversial majority decision against Foreman a month later in a heavyweight fight at Trump's Taj Mahal in Atlantic City.
8 of 25AP
Wayne Gretzky and his wife, Janet, talk to Trump in Central Park. Trump and The Great One both served on the judges' panel for a spoken essay contest called "Most Gripping Moment of My Life."
9 of 25Ronald C. Modra/Sports Imagery
Trump chats with Sammy Sosa in the dugout before a July 2000 game between the Cubs and White Sox. Sosa hit two home runs in the three-game crosstown series.
10 of 25AP
Trump waves from the press box after singing "Take Me Out to the Ballgame" during the seventh-inning stretch of a July 2000 game between the Cubs and White Sox. He was joined by future wife Melania Knauss.
11 of 25Andrew Savulich/NY Daily News Archive via Getty Images
Trump holds a personalized jersey as Rangers' captain Mark Messier receives a hat from Parks Commissioner Adrian Benepe during a special practice session in Central Park. Messier retired at the end of the season.
12 of 25Jemal Countess/WireImage.com
Trump joined Alex Rodriguez at the VIP reception for the unveiling of Carlo Beninati's portrait of the baseball player in 2004. The piece was entitled "A-Rod."
13 of 25AP
Trump talks with Patriots QB Tom Brady before a 2004 divisional playoff game against the Titans. Brady completed a key fourth-quarter drive, and Adam Vinatieri kicked a game-winning field goal in New England's 17-14 win. The Patriots eventually beat Carolina to take Super Bowl XXXVIII.
14 of 25CHAD RACHMAN/AFP/Getty Images
Trump carries the Olympic flame on New York's Fifth Avenue on June 19, 2004, during the Athens Torch Relay. The Olympic flame traveled to 34 cities in 27 countries along during the relay.
15 of 25Issac Baldizon/NBAE via Getty Images
Trump and fiance Melania Knauss lock lips on the "Kiss Me Cam" at a game between the Miami Heat and Denver Nuggets.
16 of 25Jim Rogash/WireImage.com
Trump throws out the first pitch before the second game of a doubleheader between the Red Sox and Yankees at Fenway Park.
17 of 25John Green/Icon SMI
Trump talks with NFL great Jerry Rice during the 2006 American Century Championship at Edgewood Tahoe Golf Course in South Lake Tahoe, Nev.
18 of 25AP
Trump prepares to shave the head of WWE chairman Vince McMahon, who is being held by "Stone Cold" Steve Austin, in April 2007 at Wrestlemania 23 in Detroit. Trump had put his famous hair on the line in the "Battle of the Billionaires" with McMahon. Bobby Lashley, representing Trump, beat McMahon's Umaga, sparing The Donald's coif.
19 of 25Johnny Nunez/WireImage
Trump and Shaquille O'Neal at Zo's Million Dollar Shootout Golf Tournament at Briarcliff Manor in 2007. The pair co-hosted the charity event with Alonzo Mourning, and proceeds went to Mourning's foundation for underserved youth.
20 of 25Scott Gries/Getty Images
Trump joins figure skaters Tanith Belbin, Benjamin Agosto, Shizuka Arakawa and Oksana Baiul at a benefit for the Figure Skating in Harlem program in Central Park.
21 of 25Darryl Dennis/Icon SMI
Trump and mixed martial arts star Tim Sylvia pose during the weigh-in for the Affliction: Banned MMA event in July 2008 in Anaheim, Calif.
22 of 25AP
Trump hits a shot from the rough on the ninth hole of the Deutsche Bank Championship Pro-Am golf tournament in August 2008.
23 of 25 Jeff Zelevansky/Getty Images
Former Braves pitchers Tom Glavine and John Smoltz chat with Trump during a taping of Trump's Fabulous World of Golf at Trump National Golf Club in April 2010 in Bedminster, N.J. The show, which runs on the golf channel, gives a behind-the-scenes look at Trump's courses.
24 of 25 Angus Murray /Sports Illustrated
Trump poses with a golf club during a 2010 photo shoot on the roof of Trump Tower. He owns 11 golf courses, including ones in Scotland and Puerto Rico.
25 of 25AP
Trump with the 2011 Indianapolis 500 pace car after an announcement that he would be the pace car driver at the 100th Indy 500.
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