Drew, a free agent, had been sitting on the sidelines without a team. Some clubs showed interest, but not enough to sign him before the First-Year Player Draft on June 5 and forfeit a Draft pick.
Now, Drew returns to the team he helped to win a World Series championship last season.
"Our position on Stephen as a person and as a player never changed," said general manager Ben Cherington. "Didn't change at all since the day after the season last year. It just so happened that now is the time where it was able to all come together and we were able to add a great infielder to the team, and we hope to make the team stronger in doing so."
For Drew, the past six months have been unlike any other since he last played in a game, the World Series clincher.
"It's been interesting," Drew said. "But needless to say, I'm glad to be back in a Red Sox uniform. Couldn't ask for anything better. These guys here, I know them, and had a great year last year. Just getting ready for whatever happened, preparing myself, like everybody does in the offseason. Being able to come back here, I can't thank the organization enough for thinking about me. The guys in the clubhouse are what matters the most and what they think about me."
Drew has been working out, at home in Georgia and in Florida.
"For five months, I've been working really hard, to be honest," he said. "I didn't take one day off, seven days a week, hitting, throwing, practicing with teams, running bases, everything, you name it, that I could think about to be ready, so I could be less inclined to have to sit out for a while.
"I know I worked hard. I know there's nothing I have to worry about there. I know I put all the time and effort I needed to be ready for this moment. Because I knew it would happen quick. I didn't know where. But like I said, I am excited to be back here."
Drew was placed on the active roster on Wednesday, and is expected to go to the Minor Leagues on Friday, after he clears waivers. He feels ready, but will need a few games to get back to game speed.
"The biggest issue I think will be just nine innings, playing," Drew said. "I haven't had that in seven months since the World Series ended. So just a few games, get some at-bats. I've been having AB's. That's been good to be able to have some pitching down there. So, I think the biggest key is just playing on my feet for nine innings for about nine to 10 days."
The familiarity should help to make the transition smoother.
"We've been able to add a very good player to this team," said manager John Farrell. "We know we've got some steps to go through before he comes back to us and is game-ready. But he's familiar with us, everything that is Boston. So, we're excited to put another good player on the field."
Drew will take over his shortstop position with Xander Bogaerts moving over to third base. It's a situation that could be awkward, but Drew doesn't expect any issues.
"I think what it boils down to, you look at last year and how it happened, how well he did play third," Drew said. "I'm not saying he won't be a shortstop. It's just something with Will breaking his finger and needing help, I think this presented itself and I think he will feel comfortable with it, myself and the whole team.
"I think it doesn't change the fact that he's a great player. He's young. He's 21 years old and he's done great. And you guys saw that last year. So with all this talk of me coming back, it's something that's going to help best the team and hopefully that gets resolved quick."
It was Bogaerts' versatility that enabled the Sox to make the move, according to Cherington.
"We believe Xander can play shortstop and play it well," Cherington said. "This move with Stephen is not in any way about lack of belief that Xander can play short. We're just trying to make the team better or tying to strengthen the roster. In fact, Xander's ability to play short and third allowed us to consider different options, different alternatives. Stephen just ended up being the one that made the most sense for us to pursue.
"We're just trying to get better, and there happened to be a guy who we all know is a good Major League player who had an interest in coming back here. So, we were able to sign him, as it relates to the young players, I believe committing to the young players, helping them in any way that we can to be good Major Leaguers, and also trying to improve the team in ways that aren't mutually exclusive. So, we believe that Stephen Drew helps improve the team. We also believe it might actually help some of those young players."