Aiden Konold ’26

Sports Editor

Holy Cross senior Declan O’Flynn stares down his singles opponent with a glaring intensity. This fire takes hold of Declan and has allowed him to rise to the occasion, on and off the tennis court. It has fueled Declan’s rise to the top, leading him to set the Holy Cross tennis program’s all-time singles wins record. 

“He just had the willingness to win and compete and he just liked that feeling of battling,” Gardner O’Flynn, Declan’s father, says of his son. 

Growing up, Declan competed with the same intensity in every sport that he played, ranging from wiffle ball and baseball to street hockey, basketball, and even golf in high school. Gardner played six years of professional baseball as a left-handed pitcher, but Declan wouldn’t play baseball beyond the eighth grade. 

It wasn’t that Declan didn’t like baseball. He did. But another sport was calling his name. 

When Declan turned six, his parents first placed a tennis racket in their son’s hands. Declan’s mother hit tennis balls with her son in the streets of the neighborhood soon after Declan picked up a tennis racket for the first time. He soon advanced beyond hitting tennis balls in the streets, and he started playing tennis on local courts. 

In elementary school, Declan competed in the New England Tennis Championships in Hartford, Connecticut. 

“There was one match in particular that we remember when he was on the younger side,” Claire O’Flynn says of her son. “And he battled it out in a three hour match and it was probably 95 degrees and we both remember seeing that moment and realizing that he had that type of fight in him.” 

Declan was forced to decide between baseball and tennis in eighth grade, as both sports are played in the spring in high school. 

He was attracted to the individual aspect of tennis at first because he has always liked being in control, so he decided to pursue tennis over baseball. 

“When I got to high school, I also started to enjoy the team aspect [of tennis],” Declan says. “Being on a team with all my friends has been incredible, so that combination of individual and team is awesome.” 

Declan worked on developing his game at a tennis facility near his family’s home in Ipswich, Mass. He played tennis constantly, but it wasn’t until the summer before his senior year of high school that he seriously contemplated playing tennis collegiately. 

“I had a really good year in a lot of tournaments,” Declan says of the summer prior to his senior year. “My coaches, Francisco Montoya and his group of coaches really helped me believe in myself. My parents also supported me, my grandparents, and I started to have good results.” 

In one particular tournament played on Harvard’s campus, Holy Cross Director of Tennis Brad Walulak took notice of Declan’s game. 

“I knew he had a ton of talent, but he wasn’t a really highly ranked player,” Coach Walulak reflects. “But I knew the club he was playing at.” 

Coach Walulak only had one available spot on his roster. 

“He (Declan) actually reached out to me and I felt at that point, with Holy Cross I only had one spot where the academic bands kind of fall in that he fell into and I had already made a decision on another player,” Walulak says of Declan’s recruitment. “So he kind of had to get it on his own. And I’ll say thank God that he did and decided to come here because I know there were a lot of coaches chomping at the bit to get him.” 

Though other collegiate programs recruited Declan, Holy Cross was always Declan’s top choice. His great-grandfather, Hugh O’Flynn, graduated from Holy Cross in 1933. 

“Everyone in my family had been trying to get someone to go to Holy Cross again,” Declan says. “I knew a guy on the team, Mike Prokopis, who graduated in 2022. And this was always my top choice. This was the place academically and athletically.” 

When Declan first arrived at Holy Cross, the tennis program was fresh off an 0-7 season in Patriot League play. The poor culture dated back to Coach Walulak’s arrival ten years ago. 

“When I first got here, we just didn’t have the talent to compete,” Walulak says. “We played teams like Army, we’d be on and off the court in less than an hour. Now we’re beating these teams… and that doesn’t happen without that cultural change.” 

Declan’s mindset and approach to the game are huge pieces of the Crusader tennis program’s culture shift. 

“He’s pretty tenacious in a lot of these matches,” Claire O’Flynn says of her son. “He’s determined and even when he’s down, we’ve seen him come back a number of times when it didn’t seem likely. He’s got an inner perseverance that really has helped him and it’s something that he’s cultivated over time as a tennis player.” 

Declan always wants to hit more before and after practice, and he’s always at lift, eager to get his body right. He lets nothing stand between him and winning. 

“For the last four years is, in his position no matter where he played, whether it was 2, 3, 4, 5, 6, I know there was a very strong chance that we would get a win at that position,” Walulak says of Declan, “and that’s just speaks to his competitiveness and his drive and his ability to stop at nothing to win.” 

In the 2022 Patriot League Tennis Tournament, Declan won his singles match in the six spot against Lafayette. His contributions helped the Crusaders win in the Patriot League Tournament for the second time in over 20 years. 

This season, the Crusaders defeated Navy for the first time in program history. The task was daunting, but Declan was always confident. 

“Going into that Navy match, the two or three days before,” Walulak recalls, “[Declan] pulled me aside. We had a private meeting and he said, ‘Coach, I really believe we can win this match.’”

Declan won both of his singles matches against the Midshipmen, earning him Patriot League Player of the Week honors, but he credits his teammates and coaches for the team’s successes this season. 

“Definitely my teammates, my coaches like practicing really hard with the guys. My roommate, Camilo Illanes, we would come down and play practice sets against each other and just try and push each other,” Declan answered when asked what is key to the team’s successes. “Everyone on the team pushing each other has been the difference.” 

Coach Walulak noticed Declan’s ability to uplift his teammates and push them to their potential, especially after Declan’s strong performance against Navy. 

“We made him a captain after that Navy match just for the last couple of weeks because he deserved it,” Walulak continues. “On the court, everybody looks to him.”

“Dec’s a really good teammate and seeing him win some of these matches is pretty awesome and it motivates everyone else to keep working hard and get up to the level that he’s playing at,” sophomore Camilo Illanes, Declan’s roommate, said. “He’s been playing really well this year, and he’s been pushing everyone else to play well.” 

This season, in the first round of the Patriot League Tournament against Lafayette, Declan won in both singles and doubles, leading to Holy Cross’ second win in the tournament since he first arrived on the college scene. 

     The Crusaders fell to top-seeded and ultimate Patriot League champion, Boston University, in the second round, but Declan and his teammates didn’t go down without a fight. 

“They came back a little bit and the team just was really fired up,” Gardner O’Flynn says of the Crusaders’ performance. “In the end, they could walk off the court with their heads held high after how they competed against Boston University.” 

Declan and his senior teammates have cultivated a Holy Cross program built for long-term success because they care more about the success of the program than their individual successes. Beating Navy and winning in the first round of the Patriot League Tournament is only just the beginning. 

“My one question for them (the outgoing seniors) is at the end of their four years, did you leave this place in a better position than when you got here,” Walulak concludes, “and there hasn’t been a single class in the last 10 years that hasn’t said, you know, holy smokes, it’s so much better than when I got here.” 

Copy Edited by Will Donahue

Featured image courtesy of Holy Cross Men’s Tennis Instagram