Crain's most recent comeback attempt came with the White Sox as a non-roster invite to Spring Training 2015. He performed well during rehab work and off the mound in front of coaches and front-office people who knew him well, but ultimately, things didn't work out after six games with the organization's Arizona Rookie League team. Crain had undergone biceps tenodesis surgery in October '13, and he then did not pitch for the Astros in 2014 due to his shoulder not responding and a battle with rotator inflammation.
Thoughts of the 2017 World Baseball Classic and pitching for Team Canada, the country where Crain was born, crossed his mind this offseason. Crain ultimately won't pitch in '17, but he looks at Ryan Dempster and Eric Gagne returning to Team Canada after competitive absences and isn't ready to say never.
As for what factors would convince Crain to make that retirement decision, he isn't quite sure at this point.
"It's a good question. I'm still kind of waiting to see if I get an itch either way," Crain said. "I'm waiting to see if I wanted to come back and start the rehab process and get to the point where I can pitch.
"That was 2 1/2 years of rehabbing and throwing and going back and forth. It was pretty frustrating. That's why I needed to clear my head and see where I was at, family-wise and life-wise."
Rehab work might have been frustrating, but the upbeat and affable Crain certainly loves spending time with his wife, Becky, and children Hunter, 10, Avery, 8, and Caleb, 5. Baseball, basketball, flag football, gymnastics and hockey are covered by the Crain crew.
The Crain Family Foundation also has been developed, with an expressed charitable goal of assisting families and children facing hardship. The Foundation's first event will take place on Feb. 27 at Top Golf Arizona in Scottsdale, with Crain hoping to have a player or two from each Cactus League squad in attendance. The event begins shortly after the White Sox visit the Cubs on that same day.
"Only good things come from hard work," said Crain, referring to his family's charitable work but also indirectly referencing what a potential comeback would entail. "Our goal was to have two events a year: One out here and one in Colorado.
"Each event we are going to pick different organizations to support. That's what our plan is. It's definitely something we are always going to do."
Although Crain might not pitch again, staying in baseball stands as a possibility.
"I would love to do something inside the game," Crain said. "Not necessarily coach, but be a part of an organization and bring what I've learned over my 11 years in the game to help a team succeed and talk to fans and that kind of thing. It's what I'm leaning toward right now."