Kenny Connors has always hated losing. 

No matter what it is, he needs to win. It’s the mindset he’s had since he was a kid. 

Taking part in a handful of sports when he was younger in his Glen Mills, Pennsylvania backyard, from touch football to baseball with his older sister Caitlyn, Kenny never wanted her to win. If Caitlyn won a game, Kenny likely threw a tantrum. 

“He did not like to lose,” Caitlyn said. “He was a very sore loser as a kid.”

Even when it came to video games with his friends, Kenny had to win. 

While Kenny doesn’t throw tantrums anymore, the sentiment has continued to hold true. 

Even a game of sewer ball before the Massachusetts hockey team’s games isn’t just a simple game for Kenny. 

The Minutemen typically use the game to warm up two hours before puck drop with Kenny, Jack Musa, Nick VanTassell, Cole O’Hara, Cam O’Neill and Lucas Ölvestad being the usual players to circle around the ball. They bump the ball on their knees, chest, feet and head, and if you drop the ball, you are out. If Kenny drops the ball, you’re his next target. 

“He’s the most wanted sewer guy right now because he’s always getting everyone out, but if you get him out, he’s going to put a target on your back. So if you mess with him, he’s going to come for you,” VanTassell said. “That’s pretty much with everything with him.”

Playing card games on the road with his teammates before game days, the UMass players file into a hotel room to have some fun before the competition on the ice starts. If Kenny hasn’t won a hand, he’s usually expected to make a few excuses for himself or target the guys that don’t typically play. 

Ivy League transfer Joey Musa has been a main target for the junior, with “his Dartmouth brains,” as VanTassell says, making Kenny mad.

“I love playing cards with the guys and sewer, it’s a part of the best times of being around the rink so it’s awesome,” Kenny said. 

The competitiveness that Kenny has shown throughout his life helped him excel at hockey. Coming from an athletic background with an older sister who is an equestrian, she and Kenny always had competition with each other. 

When Caitlyn first started riding horses, Kenny tagged along for her first lesson. Caitlyn quickly realized that he was better at riding than she was at the time. She got her payback when she came to Kenny’s first skating lesson, skating better than her younger brother. 

Kenny, though, remembers his first day on the ice differently. Skating around with dull blades, defeated by his lack of skill, he didn’t think he was going to enjoy hockey.

After getting his blades fixed up and talent on track, he had a change of heart.

The change of heart proved beneficial for Kenny, flying around at public skates with his father Ken. 

Ken started to bring his four-year-old son to public skates and hockey games that Ken would play with his group of friends. His friends brought their sons too, giving their kids skates and sticks to play their own game on another rink. 

Realizing his son took a liking to hockey, he started taking Kenny to more formal hockey events. In his first few years playing the sport, Ken also coached Kenny to help him get his start. 

Some of Kenny’s earliest memories come from his dad coaching him and filming his shifts on the bench during games. Ken put together a video at the end of every year to show his parents. The Connors still have those videos as memories, sometimes going all the way back to watch Kenny’s first goal and first youth shifts. 

When Kenny was five years old, what seemed like a normal day at the rink changed when the Philadelphia Jr. Flyers came knocking on the door. They extended Ken an offer for Kenny to join their eight-year-old team.

Ken informed them that Kenny was a little younger, but the junior team still allowed him to play two years up from his age group. From then on, while he continued to play baseball, basketball and football, Kenny knew that at the end of the day, it was hockey that mattered. 

“It was always hockey,” Kenny said. “I would probably miss a few games during the season of football or basketball but whenever I could, I was always playing with the team.”

When Kenny got bigger and played a tier one schedule at 13 years old, his dad and mother Andrea started to realize that their son could play past high school. 

USA Hockey eventually came to Pennsylvania to scout 15-year-old Kenny for its National Team Development Program. With big NHL names like Auston Matthews and the Tkachuk brothers coming through the program before, it was clear Kenny had something special. 

“​​It was more like a gradual run of it continues to look like he’s getting better, he’s enjoying the game,” Ken said about Kenny’s development. “He never complained about going to the rink or playing.” 

After the Glen Mills native outgrew hockey in Pennsylvania, his advisor Mark Toof helped Kenny move to Mount Saint Charles Prep School in Rhode Island. 

The move to a different state was the longest Kenny had been away from home. The 16-year-old felt comfortable moving away, though, having his best friend from home as his new roommate. In his one year at prep school, Kenny totaled 61 points on 23 goals and 38 assists in 51 games. 

“I couldn’t be happier that I did it,” Kenny said. “[Prep school] helped me grow a lot and made that next step of going to the [United States Hockey League] a lot more manageable of a transition.”

During his prep school days, Kenny stayed on the East Coast, just a six-hour drive away from his town. Moving to the USHL’s Dubuque Fighting Saints, though, put Kenny 15 hours away from his home. 

On Kenny and Ken’s long drive to Iowa, his dad reminded Kenny that his family was just a phone call away and told him, “[Kenny], if you need to call me; If you need me to come out there, just please promise me you’ll call.” 

His son had a simple response now that he had outgrown tantrums and could concentrate his competitive spirit: “Dad, I don’t get too up and I don’t get too down. I’ll be fine.”

“Having a fluctuating mindset and fluctuating emotions, [you just end] up crashing sooner or later so I feel like the closer I can stay to the middle, no matter what’s going on is better for me,” Kenny said.

While Kenny was ready to make the move into the USHL, the change came at a tough time during the COVID-19 pandemic. He couldn’t hang out with his team away from the rink, instead spending most of the day in his room. 

“I think that was difficult, but that adversity makes you into what you are today and [is] nothing that you take for granted,” Kenny said about his first year in Dubuque. 

In that season, he totaled 18 points on three goals and 15 assists in 50 games. He hit a bump in the road when he dealt with a shoulder separation injury. With it being during COVID-19, the Fighting Saints brought in Ivy League players as their season was canceled, leaving Kenny in a bottom-six role. 

He took this as a time to dial into his health. No one around Kenny ever told him when to workout or what to work on. He did it on his own, ready to learn how to be an adult. 

“I think that’s when he started to probably really tune into being more of a conscious person about what he ate, his workout regime,” Andrea said. “We never had to tell Kenny, ‘You need to work out’ or, ‘You need to get stronger in the offseason.’ I think that all started to click for him when he went out there, and he was by himself and responsible for [himself].”

In his second season with the Fighting Saints, there was a big change with head coach Oliver David leaving and Greg Brown taking over. The now-Boston College head coach helped Kenny see aspects of his game that he didn’t see before. 

Brown took the Fighting Saints from 24-25-4-1 to 40-18-3-3, helping the team go from under .500 to a tough team to play against. Kenny had a large jump in his game, producing 56 points on 25 goals and 31 assists through 61 games. 

“We had a new coach that came in and did a really good job in empowering the players and helping them build their games as well, so it was easy for me to feel like I was getting what I deserved with the work I was putting in,” Kenny said. “I had a really good team around me that year too, so I was fortunate to be a part of it.” 

The jump in his game in the USHL eventually also helped him get drafted after he was passed over during his first year of draft eligibility. 

Kenny came into his second year of draft eligibility with determination. Feeling more prepared and building confidence in his second year with the Fighting Saints, he had a better mindset going into the 2022 NHL Draft.

Leading up to the draft, when his family checked in with him, Kenny told them he was getting calls from a number of teams in the league. The team that jumped out the most, though, was the Los Angeles Kings. 

When the Kings came on the board in the fourth round of the draft, the Connors had a feeling that Kenny’s name would be called. 

The family didn’t have a big party, just a small get-together with family and Kenny’s closest friends. Ken had a Kings jersey lying out, that everyone gathered around to celebrate the accomplishment. 

“I love that he’s with a team that wants him and cherishes him and respects him and thinks he’s a great player and wants the best for him,” Caitlyn said. “I just remember that I was in tears, I was so happy for him.”

Kenny traveled to Los Angeles for the Kings development camp, but once the camp was over, he shifted his focus to his freshman season with UMass. New to campus, Kenny recognized a familiar friend in Michael Cameron, who he played with when they were kids.

Despite only knowing Cameron, Kenny quickly became comfortable in Amherst.

“I’d say the culture did a really good job in bringing us in and making us a part of the team rather than just like freshman or rookies,” Kenny said. “… I think that we do a lot of stuff with our culture in the summer that builds throughout the year that makes everyone feel important.”

Working with UMass’ sports performance coach Brandon Wickett was specifically beneficial to Kenny over the summer. Wickett helped the new freshman get into shape and feel confident heading into his first season with the Minutemen. 

The work during the offseason paid off, as he had a big jump in his game his first year. As a freshman, Kenny was second on the team in points, tallying 26 in 32 games. He credits his success both to his best friend on the ice, O’Hara, and the confidence he built during the season. 

“That was probably … the strongest I had felt in my life so far,” Kenny said. “… I think that was the biggest thing was confidence going into the season.”

An area that he values deeply at UMass is the relationships he has built while on campus. While his teammates have described him as competitive, they also have marked him as a leader.

Off the ice, Kenny is someone that all the younger guys can look up to. When VanTassell was going through struggles his freshman year, not making the lineup every night, Kenny was one of the first guys to offer advice. 

Knowing the ups and downs of hockey, Kenny and a few other teammates told VanTassell what to work on and let him know he wasn’t far off from being consistently in the lineup.

“The faster that [young guys] learn and figure things out, the better for them and the better for the team,” Kenny said. “… You never want to see [VanTassell] down in the dumps or anything like that.”

Kenny also helped his former Fighting Saints teammate Ölvestad transfer to UMass. After playing two seasons at the University of Denver, Ölvestad didn’t know if the team was the right fit for him.

In November during the 2023-24 season, Kenny got a call from Ölvestad and another one of his former teammates who was also playing for the Pioneers. They both said that they were having a tough time in Denver.

The Minutemen were losing multiple defenseman after the season, including Ryan Ufko, Aaron Bohlinger and Elliott McDermott. With that in the back of Kenny’s mind, he knew Ölvestad would fit right into UMass. 

After the season when Ölvestad started his transferring process, Kenny stayed in contact with him, helping his former teammate along the way. 

“Honestly, [Kenny] might have been the biggest factor out of everyone,” Ölvestad said. “He’s the one that I started talking to, and he was the one I was communicating with throughout the entire process, so [he] was definitely the leading role in [me transferring].”

The junior transfer coming to Amherst brought back his classic rock influence to Kenny and trips to Chipotle, adding to Kenny’s love of being the team’s social butterfly. 

“Anytime you’re with just the team for an extended period, that’s been the best times I’ve had here,” Kenny said. “It’s not like the games or anything like that, the memories are coming from trips and even just hanging out.”

Away from the rink, Kenny and O’Hara also played around with a cookie review account. Wanting to get a few laughs and being big fans of chocolate chip cookies, the two thought it would be funny to rate cookies on Instagram and get their teammates in on a few reviews too. 

Kenny marked Coronation Café as his favorite cookie in Amherst, but O’Hara prefers the simple Toll House cookies baked at home. 

When it’s time to go to the rink, though, Kenny shifts his focus to what’s best for the team. Even on days when he isn’t the most vocal, he leads by example. When the whistle blows and practice is over, the junior will likely stay on the ice for at least 30 extra minutes. 

If Kenny notices areas where the team can improve, he’ll speak up. Whatever he can do to help his team win, he’ll do. 

“He will share thoughts and comments when it matters because he wants to win,” Andrea said. “Kenny cares about winning. A lot. Probably more so than he should, but that’s just his personality. He doesn’t take a loss and joke around in the locker room, then walk out. It’ll sit with him for a while. He takes all of that very hard.” 

During Kenny’s sophomore year, the Minutemen made it to the first round of the NCAA Tournament, but their title hopes were cut short after a 2-1 double overtime loss to Denver. The loss left a bad taste in Kenny’s mouth, knowing the team was capable of making a Frozen Four run. Instead of signing a professional contract, his desire to push the Minutemen further kept him around for another season.

“I want to win,” Kenny said. “I think we have a team that should be going deep into the tournament. I don’t want to settle for that first round exit that we had last year. I want to be one of those teams that’s making noise at the end of the year. I want to be playing in the Frozen Four.”

Kenny’s competitiveness and drive to win have made him into a top UMass hockey player. No matter what the next step is for Kenny, he’ll always bring that same competitive drive from his Glen Mills backyard. 

Kayla Gregoire can be reached at [email protected] and followed on X/Twitter @Kaygregoire.