$20,001 - $30,000
Pitcher Andy Pettitte spent 18 years from 1995-2013 playing with the New York Yankees and Houston Astros. The three-time All-Star won five World Series with the Yankees.$20,001 - $30,000
The most decorated American athlete ever at the Winter Olympics, Apolo Ohno is an eight-time speed skating medalist who won two gold, two silver and four bronze medals.$20,001 - $30,000
One of the most popular players in New York Yankees history, Bernie Williams played for the Yankees for 16 seasons from 1991-2006 and won four World Series championships. New York retired his jersey in 2015 and honored him with a plaque in Monument Park.$20,001 - $30,000
Boomer Esiason spent all but one year of his NFL career playing quarterback for the Cincinnati Bengals and NY Jets. He currently serves as a radio host and analyst for CBS on "The NFL Today".$20,001 - $30,000
Brian Billick coached the Baltimore Ravens from 1999 – 2007 and led the franchise to a Super Bowl XXXV title. He was inducted into the Ravens Ring of Honor in 1999.$20,001 - $30,000
Safety Brian Dawkins was a nine-time Pro Bowl selection who played from 1996-08 for the Philadelphia Eagles and 2009-11 for the Denver Broncos. He was inducted into the Pro Football Hall of Fame in 2018.$20,001 - $30,000
Hall of Fame catcher Carlton Fisk played for the Chicago White Sox and Boston Red Sox during a 24-year career that spanned from 1969-1993. He was named to the All-Star team 11 times.$20,001 - $30,000
Chauncey Billups is a retired NBA guard who played in the league from 1997-2014. He won a title with Detroit in 2004 and was named MVP of the Finals.$20,001 - $30,000
Clyde Drexler, a former NBA guard, played for the Portland Trailblazers & Houston Rockets. He was part of the 1992 Olympic Dream Team and was twice inducted into the Hall of Fame.$20,001 - $30,000
Cris Collinsworth played wide receiver for the Cincinnati Bengals from 1981-1988 and was named to three Pro Bowls. He is also a five-time Emmy Award-winning sports broadcaster.$20,001 - $30,000
Curtis Martin was elected to the Pro Football Hall of Fame in 2012 after an illustrious career with the New York Jets and New England Patriots. He was the 1995 NFL Offensive Rookie of the Year.$20,001 - $30,000
Dale Jarrett is a retired NASCAR driver who 32 Cup Series races - including the Daytona 500 three times - and was the 1999 NASCAR Winston Cup Series champion.$20,001 - $30,000
Danny Ainge played point guard in the NBA from 1981-1995 and is best remembered for his time with the Boston Celtics, where he won two NBA titles. He currently serves as president of the Celtics.$20,001 - $30,000
Safety Darren Woodson played his entire career for the Dallas Cowboys from 1992-2004, is a three-time Super Bowl champion and a member of the Cowboys Ring of Honor.$20,001 - $30,000
Dave Winfield is a Hall of Fame outfielder who spent 22 seasons in the major leagues. The 12-time All-Star is best remembered for his time with the San Diego Padres and New York Yankees.$20,001 - $30,000
David Pollack is a former co-host of the popular ESPN football show "College GameDay". He played football at the U. of Georgia, where he was a three-time All-American.$20,001 - $30,000
Hall of Famer Dennis Rodman played in the NBA for 14 seasons and is best remembered for his time with the Detroit Pistons and Chicago Bulls, where he won a combined five NBA titles.$20,001 - $30,000
Don Mattingly spent 14 years from 1982-1995 playing first base for the New York Yankees, winning nine Gold Gloves and being named to six All-Star teams. He currently manages the Miami Marlins.$20,001 - $30,000
Dorothy Hamill is the 1976 Olympic champion in ladies' singles figure skating and the 1976 World champion. She is also a breast cancer survivor and sought-after cancer speaker.$20,001 - $30,000
Doug Flutie was named the NFL's Comeback Player of the Year in 1998 with the Buffalo Bills. A celebrated college football player, he won the 1984 Heisman Trophy while at Boston College.$20,001 - $30,000
Dustin Pedroia enjoyed a long and successful 14-year career playing for the Boston Red Sox from 2006-2019. He was named an All-Star four times and helped the Red Sox to two World Series titles.$20,001 - $30,000
"The Big Hurt" Frank Thomas is a Hall of Fame designated hitter and first baseman who was a two-time A.L. MVP and is best remembered for his time with the Chicago White Sox from 1990-2005.$20,001 - $30,000
Professional golfer Fuzzy Zoeller won two major golf tournaments - the 1979 Masters and 1984 U.S. Open - and played on three U.S. Ryder Cup teams, winning two.$20,001 - $30,000
Gary McCord is a former professional golfer and current sports broadcaster. In 1986, McCord joined CBS Sports as a golf analyst, a capacity in which he still serves today.$20,001 - $30,000
Greg Gumbel currently works for CBS Sports as a broadcaster on its coverage of the NFL and NCAA men's basketball. Over the course of his career, he also has covered multiple Super Bowls and Olympics.