The eight years between then and now probably seems like lifetimes ago.
It was 2005, Anibal Sanchez was two years removed from an elbow operation, and his fastball had jumped from 88-90 miles per hour pre-surgery to 93-95 post, and his changeup was still his money pitch.
Even for a 21-year-old, scouts saw Sanchez as cerebral. He had a presence on the mound and a game plan for every hitter.
Jon Lester was in the middle of a breakout season. He was the pitcher of the year in both the Eastern League and in Red Sox minor league system. His size and strength, along with the fact that he was a lefty, made him a scout's dreamboat. His fastball topped out at 95. He got swinging strikes with his changeup. He had starter written all over him.
But at that point, Sanchez and Lester were just prospects on a Portland Sea Dogs pitching staff trying to come into their own.
Their value was upside not even they could foresee.
"I think we were probably completely different pitchers back then," Lester said. "Naive, young, stupid, you know, throwers."
Eventually baseball would take them on different paths.
At the end of the 2005 season, the Sox shipped Sanchez to the Marlins along with Hanley Ramirez and two other minor leaguers for Josh Beckett, Guillermo Mota, and Mike Lowell.
The next season Lester made his major league debut with the Sox.
It could have easily been the other way around. The Marlins reportedly had interest in Lester, but the lefty was more or less untouchable.
Looking back, Sanchez understood.
"I don't got any surprise about that," he said. "I think I'm a baseball open mind. I think everything is business."
Still, he said thoughts of pitching at Fenway obviously ran through his mind.
"I was in Boston," he said. "I played in two leagues, really close to here, and I came a couple of times to this field, watching a couple of games.
"When I was in the minor leagues, I remember I came to a lot of games with Pedro Martinez pitching, and I said one day I would like to have the uniform and be here. But that's what you think at that moment."
It took eight years and three organizations, but Sanchez will finally get his chance to pitch at Fenway on Saturday night. He will be the Game 1 starter in the American League Championship Series for a Tigers team looking to return to the World Series after getting swept a year ago.
Lester will take the mound for the Sox.
They are both aware how much difference time makes.
"Obviously watching him over the past couple of years in Florida and now Detroit really mature and figure out who he is," Lester said. "I think that's everybody's kind of nemesis when you get called up, figuring out who you are as a pitcher. You try to model yourself off of a lot of people growing up and minor leagues, and when you get to the big leagues you have to figure out who you are.
"I think he's done a good job of that. Obviously his stats speak for themselves. ERA title winner this year. You know it's going to be tough. Just like the rest of their pitching staff. You know you've got to keep them within reach and just hope they have a bad game."
Of all the Tigers starters, Sanchez is the greatest unknown.
His only start against the Sox was seven years ago. He gave up on eight hits, three homers, and seven runs altogether, getting the hook after just 4⅓ innings.
But only David Ortiz remains from that Red Sox roster.
Shane Victorino, Stephen Drew, David Ross, and Jonny Gomes all crossed paths with Sanchez in the National League.
Beyond that, it's uncharted territory for the Sox. Whom that unfamiliarity benefits more is debatable.
"I guess that goes both ways," Gomes said. "He hasn't seen us."
Considering the Sox' hitting prowess this season, Gomes was confident the unfamiliarity will work in Boston's favor.
"It's a game of mistakes," Gomes said. "It truly is. He leaves something over the plate, I'm confident somebody's going to whack it. He lives on the edges, we're going to have to find a way to grind it like we've done in the past."
The Oakland A’s were able to figure Sanchez out in Game 3 of the Division Series. In 4⅓ innings, Sanchez gave up six runs (five earned) on eight hits (three homers).
Tigers manager Jim Leyland saw it as an aberration.
"He led the American League in earned run average," Leyland said of Sanchez (2.57 ERA). "He did not have a good playoff start. I feel very confident in him."
Sanchez knows his start will set the tone for the series.
"It's a big day for me especially because I'm going to start the series again," he said. "This team is a pretty good team, but I think every day is different. I need to keep working. I need to be focused tomorrow. My first pitch is something I look forward to every outing. I try to feel comfortable like I do all year long."