Greatest Athlete in Connecticut History Tournament: Caitlyn Jenner vs. Wes Matthews

AP Photo

It’s summertime, and that means it’s time for another SportzEdge ® Bracket-style, 64-team tournament! Feel the excitement!!!

Last year, we changed the course of modern human civilization with the Coolest NCAA Logo Tournament, which became a national phenomenon along the lines of a presidential election, Caitlyn Jenner’s ESPY speech, or DeAndre Jordan changing his mind about where he wants to play basketball.

This year, we decided to take on a question scholars have been debating since the 1800’s, maybe.

Who is the greatest athlete in Connecticut history?

There are plenty of outstanding candidates, from Hall of Fame quarterback Steve Young, to four-time Boston Marathon champion Bill Rogers, to all-time great featherweight boxer Willie Pep.

The athletes we considered must have grown up in Connecticut, and we counted only their prowess on the playing field, so coaches, executives and contributors like Walter Camp were not considered.


California's Bruce Jenner leaps jubilantly in the air after securing gold in the Olympic Decathlon in Montreal, Canada, July 30, 1976. Jenner, placing second in the 1,500 meter event finished, with a world record 8,618 points. (AP Photo)
Newtown’s Jenner leaps jubilantly in the air after securing gold in the Olympic Decathlon in Montreal, Canada, July 30, 1976. (AP Photo)

1. Caitlyn Jenner



Though she has made national news for changing her gender identity, and won an ESPY award for courage this past week, Jenner was once considered the greatest athlete in the world.

Jenner won the gold medal in the decathlon in 1976, eight years after graduating as a track and football star at Newtown High School. Jenner spent junior and senior year there.

The school named its field “Bruce Jenner Stadium,” after the Olympic champ in 1976, though it was renamed in 2001 after Jenner lost touch with Newtown. There’s no denying that Jenner was one of the greatest athletes ever to pass through Connecticut, but her connection with the state isn’t as strong as some other athletes, as she grew up in Sleepy Hollow, N.Y. and spent most of her childhood there.


Wes Matthews
Bridgeport’s Matthews won two titles with the Lakers. (AP Photo/Elise Amendola)

16. Wes Matthews 

Professional Basketball (1980-96)


The Warren Harding High Schoool grad (’77) was one of the best college basketball players in the country at the University of Wisconsin, and actually left school as a junior (less common back then) to become the No. 14 overall pick in the 1980 NBA Draft.

Though he never became a star in the league the way many people thought he would, Matthews carved out a nice career for himself. He spent 16 years playing professional basketball, including 7 in the NBA, where he was on two championship-winning teams with the Lakers (’87 and ’88).

Matthews’ son, Wesley, has also had a terrific NBA career, averaging 14 points per game in six seasons with the Jazz and Blazers. He just signed a $70 million contract with the Dallas Mavericks.

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