After long route, Stephen Halliday is ready to make the NHL jump: ‘Ottawa believed in me’

OTTAWA — The friendly family wager occurred more than a decade ago, but Stephen Halliday still remembers the terms precisely.

In the spring of 2013, a 10-year-old Halliday wanted to purchase a $25 New York Rangers ball cap from Dick’s Sporting Goods. The price tag was a little steep, so his father, James — a die-hard Toronto Maple Leafs fan — came up with a fun bet.

If the Boston Bruins defeated the Maple Leafs in Game 7 of their playoff series, James would pay for the hat for his son. But if the Maple Leafs emerged victorious, young Stephen would be on the hook for the bill.

Those terms were easy for Stephen to digest, considering his hockey fandom back then really only had one crucial rule.

“My dad loves Toronto, but I would just cheer for any team that was playing against the Leafs on a given night,” Halliday says.

On the night of May 13, 2013, the Maple Leafs and Bruins played one of the most memorable playoff games in the salary-cap era. Toronto raced out to a 4-1 lead in Game 7, making it very likely that Stephen would have to cough up $25 for his hat.

“I remember bawling my eyes out,” laughs Halliday. “The Leafs were up by three goals in Game 7 and I was thinking I had to pay him back for that hat.”

The Bruins then waged one of the most epic postseason comebacks, scoring three times in the final 10:42 of regulation time to tie the contest before Patrice Bergeron ended it with an overtime winner. It shifted the dynamics dramatically inside the Halliday home.

“After the game, I was jumping all over him. I was laughing at him,” says Halliday. “My dad was in total shock. His head was down and he was really upset.”

Halliday jokes that he was too young to understand the significance of that game at the time, thinking it was only memorable because it determined which family member paid for the ball cap.

“I didn’t realize how big that Toronto-Boston game was until like five years later,” Halliday says.

That small anecdote will certainly endear Halliday to Ottawa Senators fans, but it should also paint a picture of a young man with an insatiable appetite for hockey. He happily accepts being labelled as a “hockey nerd,” and when you sit down and chat with Halliday, it becomes quickly evident that his knowledge of hockey borders on encyclopedic.

The No. 19 has a unique history with the Senators. That jersey has been worn by some of the most gifted and talented offensive players in franchise history.

Alexei Yashin wore it in 1998-99, the season he was a Hart Trophy nominee.

Jason Spezza set a franchise record with 71 assists in 2005-06 while wearing No. 19.

And these days, Drake Batherson has established himself as a legitimate top-six forward while wearing the number.

During a conversation with The Athletic inside the Canadian Tire Centre last week, Halliday is asked if he knows the history of the jersey in Ottawa — considering he’s often worn No. 19 as a player himself.

Without hesitation, Halliday describes Spezza’s signature move when he played for the Senators.

“Spezza was patented for the fake slapper and then going five-hole on the goalie,” Halliday says. “It’s so cool to watch.”

Halliday has also closely studied Batherson, whose path he is hoping to closely mirror. Like Batherson, Halliday was drafted in the fourth round by the Senators and has required a bit of a longer path to reach Ottawa. Batherson needed parts of two seasons in Belleville, where he racked up 116 points in 103 AHL games.

“I’ve watched all of Batherson’s goals from Belleville and I’ve tried to figure out why he was successful there,” says Halliday.

That passion for watching videos and breaking down film is genuine for the 22-year-old Halliday. As a kid who grew up with social media at his fingertips, Halliday spent countless hours during his teen years creating hockey videos on Instagram.

“Every kid has their hobbies,” says Halliday. “That was mine.”

Halliday’s account has produced more than 600 videos, including highlight reels featuring his favourite players to watch like Clayton Keller, Connor McDavid and Auston Matthews. Now that he’s an NHL Draft pick, he feels sheepish about publicly sharing the handle for his hockey video account but has allowed The Athletic to peruse some of his work. And Halliday’s video editing skills are as silky smooth as his playmaking abilities on the ice.

In the spring of 2017, 14-year-old Halliday posted his first video — a montage featuring a handful of spectacular McDavid highlights.

A Patrick Kane highlight reel from 2020 begins with a sequence of Kane’s eyes and No. 88 illuminated, showing off Halliday’s evolution as an editor.

Senators fans will appreciate that he even commemorated Jean-Gabriel Pageau’s four-goal game against the Rangers in the 2017 playoffs with a slick video featuring DJ Khaled’s “I’m On One” as the soundtrack.

“It’s actually just really easy to clip it and make these highlight reels,” says Halliday.

These days, Halliday still enthusiastically soaks in as many hockey videos as he can. He’ll study Connor Bedard’s release, or try to get tips on Kent Johnson’s playmaking abilities. And this past spring, after he joined Belleville for its playoff run, Halliday put together a handful of highlight reels to pass the time in a new city. These featured 2023-24 Hart Trophy candidates Nathan MacKinnon, Connor McDavid and Nikita Kucherov as well as Auston Matthews.

“I still do them occasionally,” says Halliday. “I was bored this spring and did a couple of videos. I’m just always watching hockey.”

Halliday’s father’s work required the family to relocate from the Toronto area down to Maryland when he was 12 years old. He easily made the top teams for his age group, representing the state at various tournaments.

“But the competition really wasn’t great,” says Halliday.

As a teenager, Halliday knew he had to return to Canada if he wanted to pursue his passion for hockey.

He convinced his parents to let him move back to Toronto with his cousins, where he could be pushed by elite competition. In his first season playing with the Toronto Marlies as a 15-year-old, Halliday led the club in goals, assists and points. He instantly clicked with teammate Jamie Drysdale, often getting rides to and from practices and games from Drysdale’s mother.

After that season, Drysdale immediately made the jump to the OHL and became a star with the Erie Otters. Halliday, however, was hesitant to follow the same route as his good friend. He feared that his frame — which was already bordering on 6-foot-4 — was too lanky to thrive in the OHL.

“I knew since I was a bigger dude, I wasn’t really that well developed at that age. I wasn’t where I needed to be physically,” says Halliday. “College was the better route for me.”

To prepare for the NCAA route, Halliday once again packed up and moved on his own, this time to Bloomington, Ill. He suited up as a 16-year-old for the Central Illinois Flying Aces in the USHL, but the team immediately folded at the end of that season.

“The owner felt so bad he had to fold the team that he bought us all free suits,” laughs Halliday. “So at least I got a nice new suit out of it.”

Halliday’s USHL rights transferred to the Dubuque Fighting Saints as part of a dispersal draft. His game exploded in three seasons in Dubuque, where he established himself as one of the premier playmakers in the league. By the time his USHL career concluded, Halliday was fifth all-time in league history for regular-season points and was the USHL Tier 11 regular-season career assists leader.

But those dominant seasons and potential for an NHL team to land a big playmaking centre did not translate into success at the draft.

The first year he was eligible for the NHL Draft in 2020, his good friend Drysdale went No. 6 to the Anaheim Ducks. Halliday closely followed the draft — which was held virtually due to the COVID-19 pandemic — to see if his name would be called.

“That first year, I really paid attention. It was so cool. I thought to myself, ‘Oh my God, maybe I could be drafted,’” says Halliday. “And it definitely sucked not seeing my name called. But I used it as a motivational tool.”

When he was eligible for the 2021 draft the following summer, Halliday didn’t even bother paying attention.

“That second year, I just knew I wasn’t getting picked,” he says. “And it was really good in hindsight because it gave me even more motivation.”

In the fall of 2021, Halliday committed to attending Ohio State University at the conclusion of his USHL career. He returned for a final year in Dubuque in 2021-22 and his 60-assist, 95-point season was finally good enough for the Senators to select him in the fourth round in 2022. But once again, Halliday opted not to pay attention to the draft in Montreal that summer, knowing it was hardly a guarantee he would be selected.

“I didn’t want to get my hopes up because I was on a good path. But my dad was watching and he was the first one to call me,” says Halliday. “It was so cool to see his reaction because he’s been along for the whole ride. His reaction made me so happy.”

If there was one more family bet Halliday wanted to make, he’s pretty sure his father wouldn’t accept it.

Halliday was a standout tennis player in his teen years, following in the footsteps of his father, who played while attending Western University.

“He says he was ranked 20th in the province back in the day, but there are no online records of it,” laughs Halliday. “There are no videos of him playing either.”

James used to toy with him on the tennis courts, making his son race back and forth to try to chase down balls. But if the two of them were to ever step on the court again, Halliday is convinced things would go the other way.

“He would never play me now because he knows I’d kill him now,” says Halliday. “So he’ll never agree to play me.”

Halliday, however, rarely has time for tennis these days. He’s still working on his consumer finance degree from Ohio State and plans to finish the program remotely in the next couple of years. And of course, he’s got his sights set squarely on pushing for an NHL job this fall. He was the oldest invite to Ottawa’s development camp last week, having turned 22 the day the camp opened. Halliday was more polished and mature than the rest of his counterparts and is likely the attendee with the best chance of playing NHL games.

He turned pro this spring, leaving Ohio State after leading the team in scoring in each of his two seasons with the Buckeyes. Halliday was immediately parachuted into Belleville after signing his entry-level contract this past spring and his transition to the professional game was seamless. He led Belleville with nine points in seven playoff games, showing off his playmaking skills with seven assists.

As it stands, the Senators may have a spot or two open for competition in their bottom six in training camp. Halliday knows his game might require a bit more refining in the AHL, but as a player who was passed over twice in the draft, he doesn’t require a fresh lesson in patience.

“Whether it’s with Belleville or Ottawa, I just need to work on my game and get it to the highest level possible. I want to make an impression at camp. I want to at least show them I can play in the NHL, whether it’s this year or the year after,” says Halliday. “I’d be lying if I said I didn’t want to play in the NHL, so hopefully I get a call-up at some point. But I’m open to anything. Ottawa believed in me enough to pick me. And I want to show them that it was a good pick.”

(Top photo: Jonathan Tenca / Cal Sport Media via AP Images)