Meet Dana Plunkett, one of Drew’s first tennis buddy’s stepmom. Always a Drew fan from the start and a great friend to the Hassenbein Family.
Dear Drew,
I feel like I was able to know you just by luck. As Connor’s step mom, I naturally fell into this tennis mom life. And though it can be brutal at times (as your mom and I always talk about), it’s a role I really love. I love the competition, the stomach-turning matches, the smack talk, the random hitting sessions, the inside jokes, the broken rackets… all of it. But what I realize I love the most, is the people. And Drew, you were one of those people. You always will be.
I was introduced to you first just through stories that Connor would tell when he came home after playing with you, or watching you play. Connor would recount the things you’d say and we would all be laughing hysterically and then adopt your sayings as our everyday language. My favorite of course, will always be when you told Connor to “put the baby in the car seat”, your way of telling him to wrap up the match and get the win. Then when I first saw you play I thought I was watching an actual pit bull go to town on his opponents. Your talent was apparent and your passion was unmatched. You just can’t teach what you naturally possessed. You had a fire in you that I really admired. I will forever cherish my memories of watching you play, and watching you play with Connor. He was lucky to have you as a competitor and friend.
Drew, you were something special. At your service, your Dad asked us to give you a final round of applause. We all stood up, and cheered like crazy for you. I can tell you that we didn’t want to stop cheering. You deserve all of the applause, young man. We miss you like crazy Drew, and the applause will continue forever for you.
Meet Cole Sadofsky, one of Drew’s best friends since day 1. Partner in crime, fought like brothers, but no matter what, was the last FaceTime call at the end of the day.
Dear Drew,
Sharing a memory knowing that I will never get an answer makes me nothing but upset. The millions of memories we shared will never be shattered or taken away. My favorite memory was the Knicks vs. Cavs game. All week we were begging our dads to just buy the tickets and let us go. Both our dads agreed and we finally got we wanted. You texted me around 5 saying that your tennis ran late and that you’ll meet me at the game. Somehow you got there before me and called me when I got there. You said to me, “I’m courtside, get down here now!” I didn’t believe you but my dad kept telling me just give it a try. We decided to go down and we actually saw Drew. Drew waved to us down and as we walked down the security guard stopped me. You said to him, “Let them down, they’re with me”. Just like that, the 14 year old bossed around a Knicks security guard during one of the biggest nights of the year. We then met all the famous people and chilled there for a little.
This just shows everyone how no one was ever stopping us and when me and you wanted something, we were getting it. Drew, just because I can no longer go to Knicks games or hang out with you doesn’t mean that I don’t think about you. I love you so much and now all I can ask for is that I see you eventually.
Meet Michael Antonius, one of Drew’s friends on the tennis circuit and a tremendous competitor. One of the best players in the country and someone Drew bonded with from the first time they met.
“Dear Drew,
It is hard to write this letter to you. All of this seems unreal. My memories of you are what a nice kid off the court you are, but on court, from the first point, watch out! I knew every match against you would be tough and I needed to be on my A-game.
The fierceness you would bring, your willingness to play every point, your scrappiness…you would never go away, always playing until the end. It was unmatched and inspiring. I also must admit that I awed your backhand that simply was world-class material. We battled a few times, and you always brought the best out of me, and I hope I pushed you as well.
Your tenacity on the court was outmatched by your big heart off the court. We had a ton of fun, whether it was playing Marco Polo in the hotel pool in Orlando, or eating pizza at Park Pizza, or just hanging out in Boca Raton during the Les Petits As Playoffs. What will always be with me is your personality and your inclusiveness of others. When I went to my first Empire Cup tournament at 9 years old, watching you play, with the backward hat, superb backhand, and tenacity on full display was awesome. But even more memorable was bumping into you at the hotel lobby after I had lost. You didn’t really know me at the time, I was still the new kid, but you came over and invited me over to the table where you and other kids were hanging out. This memory of you inviting me into your circle of friends, and including me in what you were doing, left a long-lasting impression on me.
Keep pushing us from above, keep inspiring us, I will try to continue what you started…You are missed by all on the national circuit and in the Eastern section. We will remember you always.
Meet Eliza Bloom, one of Sydney’s best friends who quickly became one of Drew’s as well. He loved joking around with her & telling funny stories whenever she would come to hang out at the Hassenbein house.
“Dear Drew,
For someone as special as you, it’s not a moment that stands out. It’s a thousand moments—a decade of seemingly ordinary moments, shared laughs, time spent together, day in and day out that collectively tell the lasting story of how meaningful you are to me, and how you will always be on my mind and in my heart. And it’s these little things that I will miss the most, and that will bring a smile to my face every day.
It wasn’t a typical walk into the Hassenbein house if you weren’t banging on the window and waving at me as I walked up the steps to the door. I can hear you laughing through the window, and I can see you waving at me with the biggest smile on your face. Hanging out with Syd was hanging out with you, whether it was you coming into Syd’s room and dancing and singing, refusing to get off of her bed in your dirty clothes, making tik toks while she was in the shower, or just laughing about random things. I can’t recall a FaceTime with Syd—hundreds, maybe—when you did not grab the phone and run away with it while she chased after you. Small things. Silly things. Routine things. Life without them, and without you, just isn’t the same. I think about you all the time Drew. I miss you coaching Sydney and me from the sidelines during tennis and I feel your presence on the courts every day through the beautiful sunsets, the lady bugs, and the butterflies.
I will never stop telling stories about you. When I became best friends with Sydney at 5 years old I would have never thought that you would become the closest thing to a little brother I’d ever have. That will never change. The bond we had will always hold a special place in my heart. I love you and I will never forget you.
Meet Jesse Winter, Drew’s Level Up Travel Basketball Coach. Their bond was fueled by the passion they expressed on the court, relentless determination, and most all, they both hated to lose.
“Dear Drew,
Cool, calm and collected on the court. The basketball court that is. My point guard and extension of me from the sideline. My mini me who I loved to call “Agassi” in front of you and your boys which was guaranteed to get a laugh.
The fact that you knew you were “that dude” at 8 years old walking around with that quiet confidence that you just can’t teach spoke volumes. The kid I wanted with the ball with the game on the line, handling the double team or knocking down 2 free throws down by 1 with no time on the clock.
I always told you to remember me when you make it big time. That’s what you were, big time, bigger than life. I’ll always remember you as that but more importantly someone your peers looked up to on and off the court.
You had the “killer instinct” and “sense of urgency” to be at your best and most of all hated to lose. Just like your coach. We always had that in common and I was putting myself in your shoes every chance I got.
Coming over to train you I felt like I was giving back to my younger self. Poking fun at dad was probably the best moments we had, I remember it like yesterday. Him bragging that he was ready to join our roster and be another ball handler. “Come on Drew, no one throws a better bounce pass than me.” Always got us chuckling.
You made me proud for more reasons then you’ll ever know. Not a day has gone by where I haven’t thought of you and I’ll always carry a piece of you throughout the rest of my life. I’m a better person for knowing you and a better coach for coaching you.
I’ll meet you again, some day, hitting 10 free throws in a row before you leave.
Meet Lemon, the new addition to the Hassenbein fam who’s brought lots of needed extra love & comfort in the house❤️
“Dear Drew,
Over the past couple of months, I feel like I’ve connected with you although we haven’t actually met. I know you had touched so many lives and had a unique way of bringing people together. Well this time, you really went out of your way to try to comfort and support your Mom, Dad and Sydney. The connection is still so strong between you both. I can’t believe you’re still running the show behind the scenes.
Over the past several months, your mom has been seeing 🍋 everywhere. They unexpectedly appear in random places & on things. 2 weeks ago, Mom got a call that I was a girl & born on 9/8. Later that day, Mom saw a license plate that said Lem3098! She told Sydney she believed it’s a sign from Drew. They have been keeping me a secret from your Dad.
“LemonLime” was one of your favorite lovies you had since a baby. You referred to it as “ Lemon”, “ Lem”, or “Lemmy.” The numbers on the license plate she saw was your birth month and year (3/09) and my DOB is 9/8. Thanks to all those people who didn’t even know they were sending signs just by passing by. It helped me to find a new family with a beautiful home & fenced in backyard with lots of room to play.
I am a golden retriever and 11 weeks old. I am keeping your mom busy & driving her crazy with potty training. Sydney is the best sister, she is sweet and gives me lots of toys to play with. Your Dad is breaking all the rules. He’s giving me too many treats & messing up my schedule. We are already playing catch & running around the yard.
Drew, I am not a replacement for you. You were one of a kind and are irreplaceable. I’m here as a distraction and to bring some love into the home & hearts. I promise to be the fastest and the most athlete dog. Everything I do is for you! I hope to be “Golden” and not a “ Lemon” 🐶. DHASS ON TOP ALWAYS & FOREVER! I hope to have as many fans as you had. Please follow @goldengirlemon on Instagram.
Meet Benji, one of Drew’s favorite teammates on the Roslyn Varsity Tennis team and an all-around amazing young man.
“Dear Drew,
During the 2022 season, after beating his opponent at Plainview Old Bethpage, Drew hit some balls over the fence to our team, like they do in the grand slams. Those who caught the balls ran to the fence with a sharpie and he signed the balls like a true pro. The funniest part of this was that one of the OPPOSING players showed up waiting for a signature too.
In the 2023 season, after a hard fought match against NYS singles champion, Stephen Gershfeld, I got another signature from Drew and got one from Stephan on the same ball, expecting one day to have two pros on that ball. The video I filmed was to have official proof of the future pro signing the ball, as he hilariously admits to scribbling illegible words onto the ball.
Drew was a light in our lives and although his future was unfairly cut short, his legacy will live on forever and we will always honor the person he was.
Meet Blake, Drew’s sweetest friend since nursery school “2’s”, best Kadima partner, and queen of Grand Cayman kids club.
“Dear Drew,
We had so many amazing memories. I am so grateful for them and will continue to cherish them forever. I will always remember the several times we went to Cayman together. Many days for lunch we would find a table and have a lunch date. When we were little and rebellious we would sneak behind the security guards and steal old candy from the ginger bread houses. We played kidema on the beach for hours and swam and just had the best times. We of course made many TikTok’s and had as many conversations as possible.
You always made me laugh and smile with your heart of gold. I miss you asking me how my day was everyday. We would always laugh about the times I used to go to kids club. Last year when I didn’t go to Cayman you were so upset and made sure I booked Cayman this year. This describes the very close friendship we had.
One specific memory I remember with you was when we were partners together for every ladder. Of course I felt so cool to have the best talented tennis partner. Even though you were so incredible you didn’t care to have a good tennis player as your partner. You stayed with me. Whenever I missed the ball you would push me to do better next time and tell me not to worry. You would say swing your racket this way and demonstrated. We had so many inside jokes.
A simple thing I would like to share that defines the type of person you were was whenever I walked past you and you would be so excited to see me and say hey and ask me how I did on a test or even say something funny. It always made my day. You were always happy to help me with whatever I needed. I truly thank you for everything you have done for me Drew. I love you and I will continue to always try and impress you.❤️❤️❤️
Meet Aaron, one of Drew’s original tennis buddies from Robbie Wagner, a great competitor on the court, and a great all around kid.
“Dear Drew,
As I sit down to write this letter, a flood of memories rushes in, each one a testament to the incredible journey we’ve shared as friends and competitors. From the very first moment I met you, I knew there was something special about you. Sure, you were undeniably amazing at tennis. And yes, you were, without a doubt, the loudest little kid I had ever met. But what stood out the most, what left an indelible mark on my heart, was your unwavering passion and relentless pursuit of success.
From that initial encounter at eight years old to our final match when you were in eighth grade, so much had changed. Well, everything except for one crucial detail: I still had no chance of ever beating you. Your talent was truly exceptional, something that no one else possessed. And no matter how much I teased you about your size, your character and your game spoke volumes. People refer to you as “Hollywood,” and it wasn’t just because of your flashy style; it was because watching you play was like watching a movie unfold on the court. Your precision with every shot, your ability to read the game, it was all truly mesmerizing.
One cherished memory I hold dear is the time we spent at Robbie’s, pushing each other to excel during those drills. Yes, we would often clash and compete fiercely, but the moments when we set aside the rivalry and celebrated each other’s successes were nothing short of amazing. Whether it be Davis Cup or Rotators, you would always be my first choice.
If I had to pick a favorite memory, it would definitely be our Counties doubles match. Every point we fought for felt like the last point, and, just like so many times before, you emerged victorious. But it wasn’t about winning or losing; it was about the camaraderie, the sheer joy of playing against you. Your character was something I admired greatly. We may go days, weeks, or even months without talking, but you never failed to check in on me, offer advice on my matches, and reach out just to see how I was doing.
Our last match together, the one that marked the end of an era, is etched into my heart forever. We finished our match, met at the net, exchanged smiles, and shared our final hug. At that moment, nothing else in the world mattered. It was just you and me, doing what we loved most – playing tennis. I would give anything to hold onto that moment forever. As I embark on new chapters in my life, I can’t help but hope to be just like you. Your influence, your unwavering support, and your remarkable character have left an indelible mark on my life. I will carry your lessons, your spirit, and your friendship with me always. I promise to make you proud, Drew, for all that you’ve done for me. I love you always, little man. DHass on top.
Picking one of our many memories together is a nearly impossible task.
One of our more recent memories together was our family trip to Florida in February, 2023. It was around the time when your finger was hurt and your Dad was so concerned about letting it heal because he knew it needed to get better for the successful future you were bound to have.
You didn’t have any of your friends on the trip so you decided that you were going to hang out with me, Syd, and my friends Matt, Ryann, Hannah, and Ryan the entire time.
In order for you to go in the pool or ocean your Dad had to wrap your finger each and every time you went in the water and unwrap your finger every time you came out of the water. Well, you began to get really frustrated because my friends and I could not decide if we wanted to go in the water, stay out of the water, and sometimes we just spontaneously decided that we would go back in right after we got out. You wanted to come with us each time and although you were frustrated that you needed to keep rewrapping your finger, you were determined to keep having fun with us.
Later in the day we were going back to the room. There was a long line for the elevators and we both looked at each other and said “We’re not waiting on this line.” In my head, we were going to cut the line, but in your head we were going to take the 10 flights of stairs. We entered the staircase and of course you turned it into a competition. You said “Wanna race?” I thought you were kidding, but you began to sprint up the staircase. I started laughing knowing that I wasn’t about to run up 10 flights of stairs, but you pushed me. We kept running and running until we got to your floor. I could barely breathe but you were perfectly fine when I finally caught up to you. You stood there laughing and asked “what took you so long?”
Every time I walk up a flight of stairs, I picture you standing at the top waiting for me. I know you’re watching and I’m doing my best to make you proud.
When I first met you you were a second grader in Mrs. Palladino’s Class. My fifth graders loved being your older buddy. Your laugh, big smile and energy was contagious. Right away I hoped you would be a future student of mine.
I remember that spring at Cycle for Survival, when you saw me, it was a funny moment for you, seeing a teacher outside of school and riding a spin bike! I watched you look up to Sydney as she gave her survivor speech. You were so proud of her! Each year after that, when I would see you in the halls of Harbor Hill or at Cycle for Survival, I kept wishing, “I hope Drew will be in my fifth grade class soon.”
Lucky for me in 2019, you arrived in room 57. This is where I truly got to know you. Your drive to succeed and learn was apparent all day. No matter how challenging the topic, you didn’t give up, you asked questions, you wanted to understand.
Early in the school year, I learned about your outstanding tennis skills, when you shared your US OPEN tennis ball with the class as your “Special Thing.” Then when Mr. Hoffner, a Roslyn teacher and tennis coach, stopped by our classroom to check in on some students, you proudly told him that he would see you on the Varsity team in a few years, and he did! I remember asking you for the “former teacher discount” for your future tennis matches, which you agreed to!
These memories of you will stay with me forever and I will always feel so fortunate to have been able to spend part of your time at Harbor Hill with you.
Meet Jordan, aka “MASH”, one of Drew’s OGs who he shared a close friendship with from the start.
“Dear Drew,
Drew, you have been on my mind so much these past weeks. Beginning school and especially with the flag football season just starting. I have been missing you on my team like last year and thinking about all of the memories from that season. I always had a great time competing With you and also Against you. Tomorrow also starts our flag league with all of our friends that you were a huge part of. Some of the best memories I have ever made were on all sports teams with you for over the past 10 years.
I am remembering one specific memory from last year during the first round of our Roslyn flag football playoffs, playing together. On the first play of the entire game you intercepted the ball from the other team and returned it into the end zone for a touchdown. Our entire team was ecstatic about your amazing Pick-6 play. But, you were telling us to calm down and keep our composure since the game had barely even started. You felt that we should continue as if the score was still zero-zero and if we got too cocky then the game would have been over before it even started, and we would lose! You told us that your one play meant nothing and the game is still very close.
You didn’t make your amazing moment all about you, you made it about the team. I know often your success in tennis has been about playing on your own or with one partner, but with all of the times we have been together, especially in team sports from football to basketball and even baseball and hockey, you knew that there was no “I” in Team. You were always a great athlete and you were always thinking to make the people around you better. I remember that you had always tried to give me advice on how to make myself a better athlete. You always wanted to bring me up when I was down.
Drew, I cannot even put into words how much I miss you by my side every day. I wish you can be with me right now making even more memories than we already have. I will be thinking about you every day for the rest of my life. You will always hold a special place in my heart and I will never forget you. I will love you forever Drew.
Meet Jason – Some may know him as the dad of one of Drew’s best friends, “DD”, but to Drew, he was a close family friend and someone he loved to hang out with.
“Dear Drew,
It was July 2020 and camp that summer was cancelled due to Covid. You, Daniel, your Dad, and I decided to go to family camp at Timber Lake. We had a great couple of days doing all of your favorite camp activities. By the end of the weekend your Dad and I were exhausted from basketball, tennis, kickball, and the new high ropes course and zip line at the outdoor adventure area. We competed hard that weekend just as we always had.
\I remember your Dad pitching in the kickball game and he was striking out 3 and 4 year old kids. You and your Dad played to win and it didn’t matter who your opponent was. You guys won all of the competitions at family camp EXCEPT for the high ropes. We finally had a chance to beat you. I wouldn’t even let your Dad try the ropes course as I knew he would have gotten stuck and never would have made it. I enjoyed watching you struggle at something as you were always so good at everything and you kicked out butts all weekend. It is kind of strange for a grown man to compete with and enjoy beating a kid, but this is what you were all about. Competing and winning!! You were always looking to the next activity or competition and I was always looking to bust your chops a bit. The end of the 1st video perfectly defines our relationship.
Drew – “Get the zip line” Jason- “I will, if you make it over before breakfast tomorrow”
We have really big shoes to fill this year in fantasy football taking over your team and I know you will be pissed off and never let me hear the end of it if we don’t win the championship. I promise we will do our best for you and anything less than a championship will be unacceptable.
Meet Filip, a great competitor 🎾, trusted doubles partner, and a friend of Drew’s on and off the court!
“Dear Drew,
You and I played doubles together on multiple occasions, from local tournaments to National Clay Courts. There was a particular match that we played together that holds a special place in my memory.
We were losing the first set and even though Drew was so talented at the net, for some reason he would never poach. It started to get on my nerves a little bit so I told him that he has to start poaching and he looked at me and just started to laugh. The next point he poached and we won the point and while smiling, he looks back at me and says, “How’d you like that!” For the rest of the match we were laughing about it and ended up winning the match.
This memory holds a special place for me because it shows how Drew’s character can affect anybodies emotions in seconds and how the emotions can affect outcomes. Every time I step on the court a can feel Drew’s spirit which reminds to have fun with whoever I’m with no matter what.
Meet Logan, Drew’s classmate, a talented gymnast, and a close friend that shared his passion for competition.
“Dear Drew,
Trying to pick one memory with one of the best people I knew is too hard, so I wanted share a few. One of my favorite memories that I have with Drew is when we would both get home late from practice and do ab workouts together everyday for at least a month. As soon as I would get home he wouldn’t give me time to do anything except for FaceTime him and do our specific 10 minute ab workout that we would do every night. One of the reasons that I loved him so much was that he always wanted the best for me and pushed me to work hard until I reached all of my goals.
Another favorite memory I have of Drew is when I was at a gymnastics competition in Alabama and I texted him after the meet that I had gotten fourth place. He told me that if I wasn’t first, I was last and I had to go back to the gym and work harder. This pushed me and all I wanted to do was make him proud, which is what I strive to do everyday.
Lastly, one of my absolute favorite memories with Drew is from social studies class in 8th grade. Since Drew and I were both competitive athletes, our favorite thing to do was to plan our future commitment party that we were going to have together. I was going to go to GW and he was going to go to Harvard. Drew always gave the best advice and shaped me into the best person and athlete I can be.
Meet Sydney, Drew’s older sister, his first and forever friend.
Dear Drew,
It was the week before the Roslyn JV tennis team tryout, and I couldn’t help but feel a mix of nerves and excitement. It was a moment I had been waiting for, but as the tryout got closer, I couldn’t help but second-guess my tennis abilities. My parents tried to give me advice, to reassure me of my abilities, but Drew just looked at me and laughed. Yes, he laughed. He simply said “Put on your shoes and let’s get on that court”. So, I did just that for the rest of the week and instead of worrying I did everything I could to prepare. At first I took offense by his laughter, but really his philosophy was spot on. Drew taught me that nervousness and excitement often go hand in hand, that it’s through embracing both emotions that we can truly reach our potential. So, I made the team, all thanks to you buddy.
A year goes by. Now it was time for the Varsity team tryout. I felt those same nerves like I did before the JV tryout. However, this time was different. This time… there was no Drew to calm me down, no Drew to coach me. Well, at least that’s what I thought… Finally comes the day of the tryout. Drew’s tips from last year are racing through my head.
I ended up making the team and got to play in the starting lineup in the very first home match. As I’m warming up for my match I look down and see a ladybug on the court. Seeing the ladybug on that very court during my first match felt like a message from Drew, a reminder that he was with me in spirit, cheering me on. It was like he was saying, “I’m here with you, just like old times. Just like all those times at the park, Syd”. I ended up winning that match. The victory was not just a personal achievement but a tribute to Drew and the love we both shared for the sport. The ladybug had served as a poignant symbol, reminding me that even in his absence, Drew’s spirit and love for tennis continue to inspire and guide me on my journey. Whenever I step onto the tennis court, I carry a piece of Drew’s passion and spirit with me, and will always remember that little ladybug that made its appearance at the most meaningful of times.
