CHICAGO -- The pickles weren't good. They just weren't. They had a spicy kick, which was fine. They were also soaked in cherry red Kool-Aid, which wasn't.

Steve Montador loved them.

"People love them or they hate them. That's the deal," said Dr. Missy Holas, Montador's close friend and roommate when he lived in Chicago. "I love them. Maybe I love them because he loved them."

Holas' sister Michelle offered up the pickle taste test and then a tour of her sister's Chicago loft to point out all the other food that Montador loved.

There was barbecue from Lillie's Q, a rustic BBQ joint on North Avenue. There was sushi being served in another room from Coast Sushi Bar, a place nearby on Damen Avenue.

There were Swedish fish and bowls full of Turtles, the caramel chocolate candy. Montador, it seems, had a bit of a sweet tooth.

It was Saturday night and Holas was hosting a party at the loft near the United Center she shared with Montador, to properly kick off Daniel Carcillo's weekend with the Stanley Cup and launch his charity, Chapter 5. It was also a chance for the people who loved Montador to gather in one place, to celebrate his life one more time. Montador, a veteran of 571 NHL games, died on Feb. 15, 2015. His autopsy was inconclusive but it's believed he died of natural causes. He was 35.

The loft was expanded to accommodate all the people who wanted to attend, the garage incorporated with a lot of paint and a little additional lighting. The conversion worked not just because it eased the crowd but because it allowed guests to see the 1970 Ford Bronco that Montador had delivered last Christmas. The plan was a road trip back to suburban Toronto home this summer in the Bronco but there it sat, parked nearby, a presence in a room filled with friends and family.

Montador loved that truck. He would have loved the people at the party even more.

There were current and former hockey players. Carcillo. Ben Eager. Sean O'Donnell. Joe Corvo. Patrick O'Sullivan. Jamie McLennan. Rene Bourque.

That's expected.

There was also an artist, a chef, a doctor, a contractor, friends from the charity group Right to Play -- more people from outside the hockey world than inside.

Dana Raymond, Missy Holas, Erica Lavine and her daughter Elyanna paid tribute to their friend. Craig Custance/ESPN

Montador, a Vancouver native who grew up in the Toronto area, was the kind of guy who would strike up a conversation with anyone at a coffee shop or the golf course. It showed.

"We had so many other interests. Hockey was getting down that list. That's why we both hit it off," Carcillo told ESPN.com. "He really branched out. He lived his life the way I want to. We loved to research spirituality. We loved to read. We loved to do a lot of things guys on our team that we've met in the league wouldn't be interested in. You could learn a lot from him. And I did."

Walls filled with pictures of Montador surrounded the guests. Nearly every team Montador played for sent a framed jersey from his playing days. Unwrapped during the party was a framed Chicago Blackhawks jersey that also included pictures of Montador playing.

Montador's father and sister stood in front of that one for a few extra moments. Near the kitchen, Montador's 6-month-old son -- born four days after Montador's death -- was being passed around a crowd of people eager to meet him.

"The party was terrific," said his father, Paul Montador, a few days later. "I met some people, my daughter met some people we didn't know. We filled in some timelines and heard some great stories and saw even more the impact he had on some folks we didn't know."

The stories were great. Everybody, it seemed, had at least one good one about how Montador made them laugh.

McLennan, who played with Montador while with the Calgary Flames, was smiling when he retold a story about a phone call he once received from Montador:

"Can you do me a favor and retweet anything I tweet out on the account @TheRealGelinas?" McLennan recalled Montador asking.

"What do you mean?" he responded.

"I started this Twitter account," Montador said. "And promise me, do not tell anyone."

The Twitter account was a mix of tweets you might actually believe came from Martin Gelinas until you realize every third or fourth tweet talks about just how great his calves are.

"That's one of the things I remember telling Gelly either at the funeral or afterwards, and Gelly getting a smile about it," McLennan said. "That's just Steve. The best part about it is he didn't do it for anybody else but his own amusement. The guys would get a kick out of it. He just sat back and enjoyed having fun. That's him in a nutshell."

The last tweet was on Jan. 28.

The idea to use his time with the Stanley Cup to honor Steve Montador and help raise awareness for his Chapter 5 charity was an easy one for Daniel Carcillo.

During the season, Carcillo wrote a moving first-person piece about Montador's death for the website The Players' Tribune. It was accompanied by a heartfelt video of Carcillo calling for a better exit program for players after they're done playing in the NHL.

The video was emotional. It was raw.

Carcillo also wasn't sure how it was going to be received.

"He was really nervous to send that out," said his fiancé, Ela Bulawa.

It's one thing to get emotional when being handed the Stanley Cup. They make commercials out of that.

It's another to get emotional on a video when talking about what a teammate meant to him. How he depended on Montador to get through difficult times in his life, like when Carcillo was abusing pills.

It showed vulnerability, not an attribute usually attached to hockey players. And it's too bad because Carcillo showed just how powerful a little vulnerability can be.

"He was nervous but there was not one single negative email," Bulawa said. "People were emailing him to help."

Ela Bulawa, Wolfie and Daniel Carcillo used their Cup day to celebrate their lost friend. Craig Custance/ESPN

That's how Chapter 5 was born. Carcillo saw a deep need to help players transition from hockey to real life.

The NHL is in a good place. The on-ice product is as strong as it's ever been. Revenues continue to grow. The league is looking to expand. Ratings are up.

But there are issues that don't get talked about enough. Even with strides made over the last few years, concussions remain an issue. There's a bigger drug and substance abuse problem in hockey than anyone wants to admit.

And when a player is done playing, too often they're forgotten. They disappear from the consciousness of their teams, teammates and the league.

That some of those issues hit Montador doesn't make him a special case. It made him all too normal among NHL players.

"His brain was so [messed up]," said Holas. "He would wake up and feel crazy. We would watch movies all day some days because of the concussions."

He loved comedy. They'd watch "McGruber." "Dumb and Dumber." He loved to send friends texts from the classic "Kingpin" just to see if they knew what he was talking about. Those who knew him best always did.

Some days he'd wake up feeling great. Others, not so great.

When the autopsy of his brain came back, it revealed he had widespread chronic traumatic encephalopathy, or CTE.

"That's what a 90-year-old dementia patient would have in their head," Holas said.

It helped explain all the lost keys. Or the time Montador packed his car for a trip home for Christmas and left half of it sitting next to the car.

Montador was sober for nearly 10 years during his playing career but when it was clear his playing days were done, he started drinking again.

Without a schedule, the structure and the motivation that comes with an NHL career, he got off track. It's understandable.

It has also ignited Carcillo's passion.

On Sunday, 300 Blackhawks fans paid a minimum of $150 per ticket to be part of Carcillo's Stanley Cup party on the rooftop bar of downtown Chicago's Dana Hotel to benefit Chapter 5. They graciously paid top dollar for silent auction items, including a Blackhawks jersey signed by the entire championship team.

They lined up patiently for a picture on the roof with the Stanley Cup and then a chance to chat with Carcillo. He signed everything they put in front of him. One fan flew in from Arizona, a fan of Carcillo's since he played with the Coyotes -- a big enough die-hard that she received a call from Coyotes GM Don Maloney apologizing for trading Carcillo to the Philadelphia Flyers in 2009.

There were sticks. Pucks. This was the opposite of a relaxing, celebratory day with the Stanley Cup. Carcillo was working.

He went from fan to fan, making sure everybody felt like they got their money's worth at this fundraiser.

In the middle of it, with fans still lined up to get a picture with the Cup, Carcillo's fiancé took a moment to appreciate the effort.

"He could have done whatever he wanted with his Cup day. Anything. He chose this," Bulawa said. "I'm prouder of this than I am the Stanley Cup."

Daniel Carcillo, 30, is done playing in the NHL. At least, that's what every sign suggests. He hasn't announced his retirement and won't just yet.

On Wednesday, he boarded a plane for a trip to Florida. There, he'll decompress. There will be time for everything that has happened over the last year to sink in. A lost friend. A Stanley Cup. A new charity.

Bulawa started to notice that every time Carcillo left for a road trip last season, it got harder. It got harder to leave the family he's creating, harder to leave behind the son they call Wolfie, who is now 9 months old. Plus, there's something empowering about going out on your own terms, especially a player like Carcillo who has bounced around from Arizona to Philadelphia to Chicago to Los Angeles to New York and then back to Chicago.

Daniel Carcillo made sure to sign everything put in front of him at the fundraiser. Craig Custance/ESPN

"He's one of those guys -- physically it's taken a toll on him. Mentally, it's taken a toll on him," McLennan said. "He wants to get out while he still has a good life."

And by getting out now, he can dedicate himself fully to helping his fellow hockey players make the transition to retirement.

Who better than the guy going through it with them?

"I've already made a decision," Carcillo said. "Right now, I'm not saying I'm retiring or retired. I'm just going to Florida."

He laughed when reminded that's where people go to retire.

"Florida and Arizona," he said.

If there are any hockey players reading this, and knowing Carcillo's and Montador's popularity among those in hockey there probably are, Montador would probably tell you this: Dream big. He loved that saying. But dream bigger than the next hockey game. Dream bigger than winning a Stanley Cup.

Because even when you have that championship ring, this game can spit you out when you're done. When you retire and the next season begins, the phone stops ringing. Your teammates play on without you.

There's no itinerary slipped under your door. There's nobody checking to see what time you go to bed.

It's just you.

If everything goes well, you're playing hockey until you're 35 years old.

If things keep going well, you're living another 50 years after the NHL grind ends. That's half a century, a majority of your life.

So, ask questions. Get to know people outside the sport. Take the online classes the NHLPA will be offering in its Breakaway program. Send an email to Carcillo and Chapter 5. Find another passion outside the sport. Because you just never know -- it can all end so fast.

Sometimes, too fast.