Cheveldae taught him perseverance. Vernon taught him mental toughness. Hasek taught him how to bring his game up to the next level.
So, it is with some irony that at various times in his career Osgood had to beat out Cheveldae, Vernon and Hasek to be the No. 1 goalie in Detroit.
He summoned the perseverance, mental toughness and energy to rise to the challenge each time so he could officially hang up his pads on Tuesday as a 38-year-old with 401 career victories on his resume and his named carved into the Stanley Cup in three different locations.
Osgood's career path was littered with road blocks, but he lived out his dream because he found a way to steer around them.
"We selected Chris in the third round in 1991 and here we are today 20 years later having a conference call to announce the end of a really incredible career," Detroit GM Ken Holland said Tuesday. "In my opinion, it's a Hall of Fame career."
The Hall of Fame debate centering on Osgood is one that will rage for at least three years, when he officially goes on the Selection Committee's ballot. Some will say his numbers put him on solid footing for induction, while others will argue Osgood was the beneficiary of playing on great teams and his numbers are a result of who played in front of him.
No matter what side of the argument you want to debate, the optics are clear: Osgood belongs in the discussion.
"That's a tough one. That is definitely a tough one," NHL Network analyst Kevin Weekes told NHL.com. "I will say, though, and I've said it on the air, I think he's a Hall of Famer based on his resume, but I think it's tough because people of course are going to factor in the team he played for, too. That's a big challenge. I love what he was able to accomplish in his career, especially coming back the last few years and retooling."
While he wasn't always the No. 1 goalie, Osgood was around for the better part of Detroit's dynastic run of four Stanley Cup championships from 1997-2008. He was the starter on the 1998 squad that swept Washington in the Stanley Cup Final and the goalie that led the 2008 team past Sidney Crosby and the Pittsburgh Penguins in six games to win the franchise's 11th championship.
Osgood missed out on the Wings' 2002 championship as he was selected by the Islanders in the 2001 waiver draft and played most of two seasons in New York before being traded to St. Louis. But save for that stretch from 2001-04, when Osgood split 179 appearances between the Islanders and Blues, he was a Red Wing.
He appeared in 565 games over his 14 seasons with Detroit.
"People always say this city is tough on goalies, but I've walked on the streets and lived in all areas of Michigan and the people are great with coming up to me with words of encouragement and putting signs in front of my house when we were going to the playoffs," Osgood said. "If I could stand up and cheer for them I would. They made my career what it is."
Osgood was drafted by the Red Wings with the No. 54 pick in 1991, when he was playing major junior hockey in Medicine Hat, Alta. Holland was the Red Wings' chief scout living in Medicine Hat and he got to know Osgood because they played on the same summer ball hockey team.
"I told him, 'Don't say anything, but we got you tucked away and we want to select you in the second or third round,' " Holland said.
The two have formed a strong friendship over the years, so much so that Holland, who has four children, said Osgood has felt like his fifth child. Osgood said Holland has been like his second father.
"We never made much of a big deal out of this because we always had to keep it as professional as possible, but he was always there for me, to give me encouragement when I needed it," Osgood said. "He always said the right things. Aside from my family, he's the most instrumental in making me have the career that I did. Even when I went to Long Island, he was still supporting me. When people doubted me, he was always in my corner."
Osgood made it to Detroit for the 1993-94 season and was expected to backup Cheveldae, who was still young and coming off three straight seasons of playing 65 or more games for the up-and-coming Red Wings.
Osgood played so well that then-Red Wings' GM Jim Devellano moved to trade the 26-year-old Cheveldae to the Winnipeg Jets.
Soon after, a dynasty was born and Osgood played a major role in it.
"I think he's been an incredible competitor and with tremendous mental toughness," Holland said. "In order to succeed in the National Hockey League in goal, especially on the teams he played on, you need a lot of mental toughness because at times in the late '90s and early 2000s there was this perception that we won because of our skaters and we lost because of our goaltending. That's absolutely not true. You can't win in the National Hockey League without having key goaltending every night."
Osgood's path to 401 wins and three Stanley Cup championships was never easy. He went 23-8-5 as a rookie in 1993-94, but a terrible giveaway by Osgood led to the goal that eliminated the favored Red Wings from the playoffs in the first round of the playoffs.
Detroit signed former Stanley Cup champion Mike Vernon the following offseason and made him the No. 1 for the lockout shortened 1994-95 season.
Vernon led the Red Wings to their first Stanley Cup Final in 29 years in 1995. They were swept by New Jersey.
Osgood regained his No. 1 job in 1995-96 and finished the season with an NHL-best 2.17 GAA and 39 victories to become a finalist for the Vezina Trophy. Detroit lost to Colorado in the Western Conference Finals.
The following season Osgood handled the majority of the playing time as well, but Vernon was named the Wings' No. 1 goalie for the playoffs and led them to the Stanley Cup, picking up the Conn Smythe Trophy as well.
But soon after the Cup celebration died down, the Red Wings pulled off a stunner by sending Vernon to San Jose in a trade.
The Red Wings couldn't pass up the opportunity to give the still young and promising Osgood the full-time No. 1 job. Osgood was only 26 years old when he led the Red Wings to a second straight Cup championship in 1998.
No team has repeated as Stanley Cup champions since those Red Wings.
Osgood said he stayed in touch with Vernon during that season and used his advice as guidance. He needed some after losing Game 5 of the Western Conference Finals by giving up an overtime goal to Jamie Langenbrunner from about 100 feet away.
The goal could have buried him and the Wings, but Osgood came back two nights later and pitched a shutout to lift the Wings into the Stanley Cup Final. He helped Detroit sweep Washington for the Cup.
"You can either remember that Chris let in a goal from center ice to lose in overtime, or I remember that he had a shutout in Game 6 and we won the series," Holland said. "That's hard to do."
Osgood held his job as Detroit's No. 1 goalie for the next three seasons, but his win totals dropped from 34 to 30 to 25 and Holland decided to go in a different direction. He signed Dominik Hasek and left Osgood unprotected in the waiver draft after coming up unsuccessful in his bids to trade him.
"It was time for me to go somewhere else. That's just the way it was," Osgood said. "It was tough, like this decision (to retire), but it ended up as one of my favorite years of my career. We had a young team and we ended up making the playoffs. I enjoyed it. We had a bunch of young guys that didn't win before and they appreciated every win. It woke me up and made me realize how fortunate I was."
Osgood also realized how fortunate he was to play for a perennial winner like the veteran Red Wings. He was traded from New York to St. Louis on March 11, 2003 and played with the Blues through the end of the 2003-04 season.
When the NHL returned from a one-season work stoppage, Detroit wanted Osgood back and as an unrestricted free agent he was able to return to Hockeytown on a two-year contract to work side-by-side with Manny Legace.
Osgood, though, was re-inventing himself at the same time, trying to become a butterfly goalie so he could add some years to his career.
It was tough sledding in the beginning. Groin injuries hampered him in the 2005-06 season and the Wings brought Hasek back the following summer, meaning Osgood was again a backup.
Everything finally came together again for Osgood in the 2007-08 season and he picked up more playing time because while he was in a groove, Hasek was struggling and eventually suffered an injury. Osgood led the NHL with a 2.09 GAA and helped the Wings win the President's Trophy, but it wasn't good enough to become the No. 1 goalie to start the playoffs.
Detroit coach Mike Babcock instead went with the healthy Hasek to start the first-round series against Nashville, but Osgood knew he was ready and never pouted.
Babcock eventually moved to pull an ineffective Hasek in the middle of Game 4 of the opening round against Nashville and starting with Game 5, Osgood and the Wings ripped off nine straight wins. They went on to win the Stanley Cup in a six-game series against the Penguins.
"I was like a horse getting ready for the Kentucky Derby," Osgood said. "I remember Drapes (Kris Draper) coming back to me and saying, 'This is your time, you've been waiting for this.' I was. I was never nervous. I felt great."
Osgood was supposed to be No. 1 goalie again for the 2008-09 season, but he struggled so bad that Ty Conklin had to emerge and hold the Wings in the race until Osgood could return to form. Despite finishing with a 3.09 GAA and .887 save percentage -- the worst statistical season of his career -- Osgood was again named the starter when the playoffs began.
He again answered the call, bringing Detroit back to the Stanley Cup Final.
This time, the Wings couldn't repeat as Maxime Talbot burned Osgood twice in the second period of Game 7 and Pittsburgh hung on for a 2-1 victory to claim the Cup.
Jimmy Howard's emergence the following season dropped Osgood to No. 2 on the depth chart. He stayed there until sports hernia surgery ended his final NHL season three months prematurely.
"Just a phenomenal career," Red Wings coach Mike Babcock told NHL.com. "He and his wife should be proud. I mean, 400-plus wins, three Cups and more importantly than that a great husband, father and unbelievable teammate. A real competitor and a lifetime Red Wing. Good for him and we're proud of him. We look forward to him joining our organization as a coach."
Follow Dan Rosen on Twitter at: @drosennhl