On the field, the husky right-hander pitched through pain to help end the club's 86-year championship drought in 2004 -- and then contributed to another World Series title three years later.
Off the field, the opinionated observer appeared at a congressional hearing on steroids use and campaigned for former President George W. Bush.
From a Thanksgiving dinner in 2003 at his Arizona home where Boston general manager Theo Epstein lured him back to the team that drafted him in 1986 to his retirement Monday, Schilling made his mark in a city of demanding fans.
"I think in the end, we really didn't need to sell it," Epstein said Monday. "The Red Sox were perfect for him, because he likes the big stage, the history of the game. He likes to be the center of attention. It was a good fit."
Schilling enriched that history throughout a career that began with Baltimore in 1988 when he retired the first major league batter he faced, Boston's Wade Boggs, on a ground ball. He threw his last pitch in 2007, a ball on a full count to Colorado's Todd Helton in Game 2 of Boston's World Series sweep.
A shoulder injury and surgery sidelined him for all of 2008. Then, at age 42, he had to weigh long hours of rehabilitation against the alternatives -- spending more time with his wife and four children and focusing on his video game company.
So Schilling, a free agent, scrapped his idea of possibly signing with a contender in the second half of the season.
As successful as he had been in 20 years of pitching for Baltimore, Philadelphia, Houston, Arizona and Boston, as competitive and driven as he was on the mound, he had stood on it for the last time.
The $8 million, one-year contract he signed before the 2008 season was his last.
"It is with zero regrets that I am making my retirement official," Schilling wrote on his blog. "The things I was allowed to experience, the people I was able to call friends, teammates, mentors, coaches and opponents, the travel, all of it, are far more than anything I ever thought possible in my lifetime."
Schilling pitched brilliantly in Game 6 of the 2004 AL Championship Series against the New York Yankees just days after surgery to suture a loose tendon to his right ankle.
The procedure was repeated before another outstanding outing in Game 2 of the World Series sweep of St. Louis as Schilling led Boston to the title in his first season with the Red Sox after he was acquired in a trade a few days after Thanksgiving.
In both games, blood seeped through his sock.
"I think people will definitely remember that, but I would say three championships is a pretty big deal," said Yankees outfielder Johnny Damon, a member of the 2004 Red Sox. "It was a nice career. The writers will think about it in a few years if he's Hall [of Fame] material. He definitely took advantage of what he was given."
The bloody sock from the World Series is now in the Hall of Fame.
"It was freezing, raining, cold as hell, and the guy just had open surgery on his ankle," Boston designated hitter David Ortiz said. "A lot of people come up to me and ask me, 'Hey, he was bleeding for real?' I'll tell you what, man. He showed me a lot of guts. I had a lot of respect for Curt."
Schilling finished with a 216-146 record and a 3.46 ERA. He is tied for 80th on the career wins list and his 3,116 strikeouts ranks 15th overall. He won more than 20 games three times from 2001 through 2004.
All that may not be enough for him to get to the Hall of Fame.
But there's much more on his resume: an 11-2 postseason record, the best of any pitcher with at least 10 decisions, with a 2.23 ERA in 19 career starts. He also was co-MVP of the 2001 World Series with Randy Johnson while in Arizona.
Then there was his focus. Red Sox manager Terry Francona rarely spoke with him the day he pitched.
"The surlier, the better," Francona said. "The few times where he did speak, I remember thinking, 'He's not ready to pitch.'"
Schilling's shoulder injury came to light early in February 2008 when he disclosed on his blog that he and the team disagreed about the best way to treat it. He preferred surgery while the team wanted him to rehabilitate it in hopes of having him pitch that year.
Eventually, both sides agreed that surgery was best and he had it on June 23.
"I talked to him about a week ago," Dr. Craig Morgan, who performed the operation to repair his right biceps tendon and labrum, said Monday. "He said his shoulder felt fine. He's just enjoying being with his family. And the other thing he told me was he wasn't quite sure he wanted to put the time commitment and do four to six hours of exercises every day, which is what's required to come back to pitch."
Schilling was 9-8 with a 3.87 ERA in 2007 when he spent seven weeks on the disabled list with shoulder tendinitis. But he was 3-0 with a 3.00 ERA in the postseason.
"[He] never backed down from any challenge," Epstein said. "One of the things people didn't realize about Schill is that he was really motivated by fear. Fear of failure."
He wasn't afraid to express his opinions.
In July 2007, he said on HBO's "Costas Now" that the refusals of Barry Bonds and Mark McGwire to address speculation about steroids use are tantamount to admissions. Last September, he said during a radio appearance that former teammate Manny Ramirez "was always kind and nice for the most part, but he'd show up the next day and say, 'I'm through with this team, I want out now.'"
Now Schilling is out -- leaving behind a distinguished career and moving on to a life away from the spotlight.
"The game was here long before I was, and will be here long after I am gone," he wrote on his blog. "The only thing I hope I did was never put in question my love for the game, or my passion to be counted on when it mattered most. I did everything I could to win every time I was handed the ball."