Men's Sports Sports

“It taught me that fight”: Dyslexia is no match for Jack Anastopoulos

By Joe Arruda

He laid in bed, a family-sized bag of original flavored Cape Cod brand potato chips by his side.

 A 10-page paper was on his mind. 

Jack Anastopoulos types and deletes, types and deletes. 

He had already been in constant communication with his professor, asking for help with the prompt. 

Hours later, when that block was still there, he kicked off his navy blue sherpa throw blanket, got out of bed and walked three doors down the Gulick 4C hallway to his friend’s room. 

He knocked on the door.

No response, so he walked in. The sound of the wooden door opening wakes up his friend, “Jack what do you want?”

“Will you help me with my paper?” he asked. “I just need help with the outline, how is this going to be 10 pages?”

On the eve of spring break, most college students celebrated the completion of their assignments, looking forward at the week to come. But, for Anastopoulos, it was grind time. 

“He’s a good guy, but he doesn’t sleep a lot,” his first-year roommate Sean Andrews said. “He would always be doing his work in his own space, on his laptop, very focused on it. He talks to teachers a whole lot. 

“He would email with all our teachers all the time. I had a ton of classes at the same time as him because we were both taking the same gen-ed classes and if I didn’t know what the homework was, he always was like, ‘Oh, yeah I emailed the teacher it is this and this, she wants it like this.’”

The tennis team was leaving for Florida in the coming days, but before he could get excited, one grueling assignment stood in the way.  

That late night grind just before a deadline was nothing new for Anastopoulos when he first stepped foot on the Springfield College campus.


Beginning as early as kindergarten, reading and writing posed significant challenges for him. He wasn’t able to write his name, and fell behind from the start. 

He was just different. 

Years later, the problems continued. He sat in a fifth grade classroom composed entirely of children who were caught up with the curriculum, going to school was no chore for them. But, Anastopoulos still could not manage to read a book.

“I could read small things, like those books that would say stuff like, ‘cat,’ ‘pig,’ ‘dog,’ stuff like that,” he said. “I could read like the one syllable and sometimes two syllable words, but when it got into longer words, or even with more letters, it just confused me, I couldn’t. And also words that would trick a lot of people, like ‘island,’ I just wouldn’t understand. I would think ‘is-land.’”

The public school system in Brookline, Mass. was not well enough equipped to accommodate him. 

He was constantly being removed from class to get extra support which often consisted of being read to for a short period of time and then spending the remaining time playing basketball or other games. It wasn’t for kids with problems with the classroom, it was for kids who were problems in the classroom.

After realizing how much of an issue his setback with learning had become, Anastopoulos underwent a series of tests to diagnose what was causing his trouble. 

The doctors discovered that he had a learning disability, and diagnosed him with dyslexia. 


After his diagnosis, Anastopoulos and his family knew that they would be able to get financial assistance in paying for a school that would be more fit to help him succeed. So, they found Landmark school in Beverly, Mass., just under an hour away from his home in Brookline. 

“Landmark specializes with kids with learning disabilities, like dyslexia, ADHD, ADD, to the point where it affects them in the classroom,” he said. 

The environment was well-suited to his needs. Landmark featured an almost utopian structure intended to benefit students with his exact complications.

“The unique thing about Landmark is that there’s a one-to-one tutorial for each student which is very uncommon, and the class sizes are very small compared to public school. At Landmark the largest class is eight students so it really allows teachers and students to work together more closely, work on areas of weaknesses, and exploit those areas of strength that those students have,” one of Anastopoulos’ tennis coaches at Landmark, Khiet Chhu, said. 

The school focuses on teaching students strategies which they can use to manage their time and workload in order to be successful doing similar work as other students at that age. 

“It was weird actually doing homework, because I never did homework before because they knew I couldn’t do it. A big change was that the teachers were on you now,” Anastopoulos said. “There was nowhere to hide in the classroom. It was like six to 10 kids in the classroom compared to my public school where it was like 30 to 45.

“So I couldn’t just like sit in the back and they couldn’t just forget about me. They were on you the whole time, so it was weird because I actually had to do homework now and I was used to just sitting at home after school because I couldn’t do it. Now I actually had work to do.”

The strategies taught at Landmark worked substantially, and what used to be confusion over polysyllabic words turned into a greater understanding of what he was looking at, and the world around him.

Anastopoulos said, “When I finally did learn how to read, it was so crazy to me because I switched schools and it only took them a year to get me learning like the basic parts. And it took my other school six years and they couldn’t do it. 

“My big thing was I remember being able to read like cereal boxes now, I was able to read signs, small things like my own road sign, things like that. That was the biggest difference I’d say because now I wouldn’t just be looking at thing for the colors, and now I could actually understand what was going on.”

The change was difficult for him in a slew of different ways. 

As with any child, switching schools means losing a group of friends who they have often grown up with for the majority of their lives. This is followed then by entering a brand new, uncomfortable situation in which a child is isolated, forced to find a new group who might, or might not, open their circle to draw him in. 

For Anastopoulos, leaving his friends entering the sixth grade meant leaving most forever. To his surprise, only two or three of his friends from public school would continue talking and hanging out with him when he was home. 

But, the situation he entered was a friendly beast. 

“Making friends at the new school was actually pretty easy because everyone was the same in a sense,” he said. “Everyone had similar issues, everyone came from a similar background, similar school experiences, similar problems with the districts about IEPs and things like that.”

But, because Landmark is a private school, most of the students live far away, and it was hard for Anastopoulos to find a group that would still exist outside of Beverly. 

The difficulties translated further than just the social aspect. 

As a person with a learning disability, fitting in was hard enough. And transferring to a school widely known for its focus on that exact difference would only make it more difficult when he returned home.  

He welcomed questions of, ‘Isn’t that school for kids who are like stupid?’ Those comments made an impact on him, hurting him in the moment but motivating him as time went on.

“Going through all of that made me a better person I would say because now seeing someone who is different getting taken advantage of or getting pushed around just because – for me it was over the smallest thing, it was about reading,” he said. 

“Also in like sixth, seventh, and eighth grade when I switched schools and would come back, they would be like, ‘How’s the slow school?’ It’s just another school. We all go to college now, we all work now, we all do the same thing, we just went to a different school.”

The words sometimes translated to physical altercations. The ignorance of adolescence was too much to handle as a middle school student who didn’t necessarily understand what made him different. 


For Anastopoulos, the way to overcome this was through sports.

Jack Anastopoulos participating at the Springfield College tennis team’s Spring Break tournament in Florida

“When I was younger, playing a sport was a way that I could be like everyone else, no matter what sport it was,” he said. “Whether it was soccer, baseball, football, basketball, anything it was the only way I could be like similar because I was just as good –if not better– than everyone else, compared to in the classroom where I was horrible.

“In the classroom it was tough because I couldn’t do the same things as everyone else, but when I could play a sport and be better, that’s why I loved it so much.”

The internal push that got him through tough academic assignments translated to his playing style and attitude he brought to the tennis court.

Chhu said, “He started out playing doubles for us, which was probably not where he wanted to play, but he was always a team player. In doubles, he played with a senior on the team when he was a freshman, and he was always a really scrappy kid. 

“I remember that about him when he first started, just fighting, clawing for every point. I knew we had a good one for our team in the future, and I think his best year was his senior year by far.”

It was a different kind of fight when it came to sports; one that he was more prepared for. 

But, the childish taunting did not cease. 

“We always knew that other schools were going to say stuff whether it was tennis, soccer, anything, they were going to make fun of us whenever they could,” he said. “My attitude towards tennis wasn’t always the best especially going into freshman year because it was just so mental. You’re all on your own out there.”

The banter was not only noticeable to the players, but it was almost expected to come – especially in more physical sports like soccer. 

“It’s usually in the form of trash talking. Particularly in soccer, there’s a lot of stuff that goes on on the field, other kids, other teams, some of it is trash talking, and some of it is just harsh,” Dan Ahearn, one of Anastopoulos’ tennis and soccer coaches at Landmark, said.

As he got older and more mature, Anastopoulos turned to the sense of humor that he is now recognized by to deflect the negative comments. He knew that at the end of the day he had friends to fall back on, and opponents were running out of sayings that he hadn’t already heard.


Towards the end of his high school days, Anastopoulos had developed from a kid who first picked up a tennis racquet at a club in Florida to pass time with his grandparents, into an athletic player who had a chance of actually moving on to a collegiate career. 

This was something new for the tennis program at Landmark.

Clad in a gray Vineyard Vines quarter zip, which was unzipped to show off his blue and white dress shirt, all topped off with a matching tie, Anastopoulos sat at a table that was draped with a blue and gold cloth with his high school coaches, and a representative from Springfield College. 

He grabbed a red pen in his right hand and with a smile stretched across his face, signed his name on a letter of intent to play tennis for the Pride, instantly becoming the first –and only– Landmark tennis player to sign with a college. 

Anastopoulos signing his National Letter of Intent in 2018

The college search process was much different for Anastopoulos than it would be for most other athletes. His main focus never veered from the academics. Getting enrolled was one step, but getting through school was a larger one.

“In terms of choosing, for us it was always more important for Jack to have the right academic fit where he was going to get the support he needed,” Chhu said. “We knew that he would be okay in terms of his tennis, he was going to work hard, he was going to be able to make an impact on a team and work his way up the ladder, but the tricky part would be to make sure the academics don’t fall off because of that.” 

When it came down to it, Springfield offered the best mix of both a tennis program where he would fit in well, and an academic system that would support him. Ultimately, the commitment of the Springfield College coaches, actually traveling to watch him play, is what drew him in. 

Time management: A concept that is hard to grapple with for any student, and one that is much harder for students with learning disabilities, let alone student-athletes. But, with the strategies that stuck from Landmark and the Academic Success Center at Springfield College, Anastopoulos is able to pair his scrappy nature and get it done. 

“The three weeks getting ready for a paper, a student with dyslexia might need additional time and planning to really get rolling,” Andrew Wilcox, director of the Academic Success Center, said. “Sometimes it’s just making sure that they’re really getting that time to ask the professor more questions, because dyslexia impacts your ability to break down text, which can then affect your comprehension of what it is, and then also to produce. 

“But before you produce, you really have to understand clearly what is being asked of you. Professors usually come up with a little, sort of brief summary or they may have a rubric which then explains things. Being able to have the time to talk through fully what is being asked of you is a pretty key step.”

Juggling the amount of time he spends with tennis – whether it be practice, lift, or matches – and in class, a forced set period of homework time has benefited Anastopoulos. But, sometimes that self-designated time is not enough, forcing him to stay up late.

“It started in high school because I would have sports after school and I would take the train back home to Boston and I wouldn’t get back until like 8 or 9 p.m., and I would get my homework done at 11 or 12:00, and wake up at 5:30 a.m. to go to school the next day. So I was used to not much sleep, obviously it’s good to get sleep and you want more, but it’s prioritizing at the end of the day,” he said.

“A big thing from that is that it taught me that fight. To keep working, to keep trying, and it is something that I can carry on in life as well because if I don’t work my hardest I’m not going to get anywhere.”


Just as the clock struck 4:00 a.m., Anastopoulos hit the period key one last time, submitted his essay on BrightSpace, and finally laid his head on his pillow and shut his eyes.

Featured photos courtesy of Springfield College Athletics and Jack Anastopoulos

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