The trio would hang out often, but it was Toews and Kane, who roomed together on the road, who were almost always the ones subjected to the hijinks of their veteran teammates.
One prank stands out in particular.
Adam Burish and Patrick Sharp hung a room service card outside the two players' hotel room door, but not before checking off each and every breakfast item available on the menu, Bolland recalled. They made sure to schedule an extra-early delivery time, too, so that Kane and Toews were roused from sleep at the crack of dawn to an entire brigade of carts festooned with Belgian waffles and vegetarian omelets and probably a pastry tray or two.
Kane was usually the first one to laugh along at the stunts; Toews was not always as easily amused. But, the team loved it, initiating the future stars with a few jokes at their expense.
Now, seven years since they first burst onto the scene, the landscape has changed dramatically. Kane and Toews are no longer the rookies.
"They're not the young guys anymore," Bolland told ESPN.com. "They're veterans now, leaders of that team."
And both Kane and Toews realize the responsibility that comes with that and the importance of working in concert. Though the two are about as different as players can get -- Kane the fun-loving and dynamic playmaker who can electrify with his skill; Toews the consummate captain, hardworking and serious -- they have found harmony in that balance.
"Kane is super skilled, wants to have the puck, makes plays, and Toews always competes, always wins battles, always tries to lead his team. When they put those two on the ice, it's pretty hard to defend," former Norris Trophy winner and Boston Bruins captain Zdeno Chara told ESPN.com.
Their integral importance to the club was made clear when the two players were locked up long-term back in July, inking matching eight-year, $84 million deals that will kick in next season and, as it currently stands, will earn them the highest annual average salary ($10.5 million) of any player in the NHL.
As important as the two have been to the Blackhawks' success in recent years -- the team captured Stanley Cup championships in both 2010 and 2013 -- the Hawks made it clear they want them to be just as instrumental in the team's future.
Instead of protracted contract negotiations, the ink was already dry on the deals a mere eight days after they were eligible to re-sign. Clearly, securing the two players as they enter the primes of their careers was a priority.
"They wanted to be here and we wanted them to be here. It works both ways," Blackhawks chairman Rocky Wirtz told local reporters in early October. "It just shows, think of the story you would've got if they waited until April or May to come in and say we are going to sign a contract. We wanted to eliminate that, get on the ice and get on with our business."
According to someone with knowledge of the negotiations, the process went about as smoothly as possible ("It was never acrimonious," the source told ESPN.com). Both Kane and Toews, who share an agent in Pat Brisson, were uncomfortable with making more money than the other. In fact, both the kid from Winnipeg, Manitoba, and the kid from Buffalo, New York, found the amount of money they were about to make difficult to fathom.
Both wanted to be paid fairly, but neither wanted to be the reason for a weakened product around them or a fellow teammate traded elsewhere. Once the two sides came to an agreement on the AAV, the only complicating factor was figuring out how to structure the deal in a way that made both players comfortable yet did not completely tie the Hawks' hands.
Such is the challenge in the salary-cap era.
"I have always said the most important thing for us is you can't get star players. Once you do get ones, it's so hard to win. You got star players here who have shown the ability to win. They want to be here. It's not even a discussion point. I'm just thrilled we have two of them," Blackhawks general manager Stan Bowman said after signing the two this summer. "Most teams would die to have one of these players on their team. We have two of them here. We're very fortunate. The rest of the stuff will work itself out. We put a lot of work into finding young players and surrounding these guys with a great supporting cast."
Now Kane and Toews have not only years of experience to their advantage, but also the peace of mind in having long-term security. That should be huge as the Blackhawks battle for one of the top spots in a stacked Central Division.
"Most teams would die to have one of these players on their team. We have two of them here. We're very fortunate." Blackhawks GM Stan Bowman on Patrick Kane and Jonathan Toews
And considering how close the Blackhawks got to reaching their third Stanley Cup finals in a matter of five years last season -- falling in overtime of Game 7 of the Western Conference finals to the eventual Stanley Cup champion Los Angeles Kings -- they should be just as competitive this season.
"Who knows what could've happened? It was an amazing opportunity that we missed and we have to start all over again," Toews told ESPN.com in a recent telephone conversation. "We beat some good teams on our way and [those teams] are always getting better. The road back to this point is not getting any easier. That one hurts, but we've gotta get over it and see the task in front of us."
Putting that heartbreaking series behind them remains a tall order, however.
Though Kane said some of his teammates abstained from watching the Stanley Cup finals after they were eliminated, he couldn't help himself.
A hockey lover at heart (with a passion so pure that Bolland describes him as almost "geekish" about the game), Kane watched as the Kings hoisted their second Cup in three years, no doubt envisioning the alternate ending.
"It's surreal when you watch someone else win the Stanley Cup," Kane told ESPN.com last month. "It's almost like not real, like it's a dream, but it's inevitable, right?"
It doesn't have to be in 2015, not if Kane and Toews perform to potential and the Blackhawks are, as expected, one of the elite teams in the league.
Both players are coming off outstanding 2013-14 campaigns, with the 25-year-old Kane registering 69 points in 69 games and the 26-year-old Toews finishing with 28 goals and 68 points in 76 games. Kane said he worked this summer on skating in particular and hopes he can become more of a dual threat. He wants to see his game evolve, even though opponents insist it already has.
"As the years go by, they're getting more and more experienced and they have kind of developed into their own characters on the ice," Chara said. "Maybe early on, we could see that they were not as mature, maybe as players or individuals, but now they've really matured and they play a certain way."
With that progress, the relationship between Kane and Toews has grown as well.
Though different in both temperament and demeanor, they seem to appreciate what the other brings to the table. Yin to each other's yang and what have you.
"We roomed with each other the first five years of our career and I think there were times we probably wanted to kill each other," Kane said with a laugh. "Now we're a little more independent, but I think we've become better friends and become closer."
Toews concurs: "I absolutely agree. In the beginning, we were both the types of guys that just wanted to be the best. We might've been more in competition against each other in the beginning, but now seeing the team success we've been able to be a part of, I don't think anyone feels they have anything left to prove to each other. We've been so lucky to be surrounded by a great team and to be at the center of it."
That growth, both on and off the ice, is unlikely to stop anytime soon, according to Bolland, now a member of the Florida Panthers.
And that makes them all the more dangerous as a result.
"They are at the peak of their careers," he said. "And I think they have more and more to give."
Scott Powers of ESPNChicago.com contributed to this story.