O’Leary Continues Annual Wiffle Ball Tradition


Seniors Tyler Page, Danny O’Leary, and Jack Barry will play as a team in O’Leary’s wiffle ball tournament.

Aidan Chariton

From the imaginary runners or the limitless “junk” balls to pegging rules, wiffle ball has long been a fun game for teenagers in the spring and the summer. For senior Danny O’Leary, wiffle ball is more than just a game—it is a tradition. For the past three years, students at WHS participated in an annual wiffle ball tournament organized by O’Leary.

Four years ago Kevin O’Leary —WHS graduate of 2016—hosted his first wiffle ball tournament. His younger brother Danny then decided to start hosting his own tournament, and has done so for the past three years.

“It’s a great American game,” said Danny. “My love for wiffle ball is what lead me to start the tournament.”

The 2018 tournament is run in a double-elimination style, and consists of 13 teams—each with three players that paid $5 to play. Basically, once a team loses two games it is eliminated from the tournament.

Although freshman and sophomores took part in previous tournaments, this year’s lineup is composed of all upperclassmen. Multiple seniors are returning to the tournament this year as veterans, and plan on going all the way.

“This is my second year,” said WHS Baseball senior captain Tyler Page. “My expectations are to hit dingers, make history, and win it all.”

Unlike a baseball field, O’Leary’s backyard — the playing field for the tournament — is not shaped symmetrically, so batters take a different approach to hitting than they usually would. Particularly, the boundary in right field is shorter than the center field and left field boundaries, making it more susceptible to home runs a primary target for hits.

“Right field is the closest [boundary], so hitting lefty at Dan’s is a huge advantage,” said senior Henry Dundon. “Brett Lavanchy [and I] are both lefties, so we should do well.”

The teams are made and the tournament kicked off on Saturday, Apr. 14. Win or lose, at minimum the participants will get some fresh air, maybe a sun tan, and hopefully some laughs in the process.   

Danny said, “We got a good turnout this year, and I think we will have a lot of fun.”