It's all coming back to J.D Drew.

There's Monday's news that his brother, Stephen Drew, is coming to Boston, agreeing to a one-year deal to play shortstop for the Red Sox. (A notion J.D. didn't feel comfortable talking about when reached by phone Sunday night.)

And then there are the memories that Mike Napoli's situation has resurfaced.

Since the Red Sox first agreed to a three-year, $39 million deal with Napoli, the team has now come to terms with four more free agents -- Shane Victorino, Koji Uehara, Ryan Dempster and now Stephen Drew. Yet, still, there has been no word when it comes to the first baseman's deal becoming official, with the prevailing belief that medical concerns have resulted in the delay.

That's 14 days of silence. For J.D. Drew, that's nothing. His wait lasted 52.

"Fifty-two days … The worst part of those were the first few days," Drew said. "With Theo [Epstein], our relationship, and Scott, it was understood we were going to get this deal done. I don't know what they're telling Napoli. I'm sure it's similar to that."

Drew might be the standard bearer when it comes to an example of a contract being reworked due to medical issues. His detour started in a hotel room on Dec. 13, 2006, when it was relayed that he would not be sharing a press conference with Julio Lugo as planned, and stretched all the way until late January 2007.

"It would have been nice to work it out in 20 days instead of 52 days. It was a unique situation to say the least," Drew said. "I can say this: It got me out of a big, stinking press conference."

Drew can relate somewhat to whatever Napoli might be feeling, although while such situations are similar, they are, as the former outfielder points out, rarely exactly the same.

The Red Sox have executed a few of these such deals, ones that protect the team against medical concerns using clauses that will kick in if there is a problem with the specific ailment. For Drew, it was a right shoulder that had been operated on the offseason before signing with the Sox. Another example is John Lackey, who had a vesting option that became a team option at the major league minimum when he had to undergo Tommy John surgery on his right elbow.

It's a team policy that started when principal owner John Henry decided he would rather gain peace of mind through such clauses instead of insurance after being burned by an Alex Fernandez policy with the Marlins.

But, again, it was J.D. Drew who representrf one of the first, and perhaps most intriguing, cases.

"The one thing that was tough was I was there thinking that I was doing this press conference with Julio Lugo, and I thought it was odd nobody was telling me what we were going to do," he recalled. "I remember talking to Scott [Boras], 'What's the deal' Do I need to speak?' He just said they were in a holdup after the physical. That's probably what I remember the most, not the 52 days but just the first explanation that they weren't happy with what they found. I think as a player it was tough to understand because you're still capable of playing.

"I knew I signed a big deal and people are going to want to make an announcement. So I'm at the hotel and I'm waiting around and Lugo has his press conference. I'm like, 'Scott, what's going on.' He just said, 'They're having some issues with your physical. Go home and we'll get this resolved.' He was pretty perturbed. For the next 52 days I had to spend my own time and money to refute some of the things that were going on and get the process to the point where we had to ultimately put a clause in the contract."

What baffled Drew was that his right shoulder had been of little concern. He had experienced micro-fracture surgery leading into the '06 season (a procedure that drills holes in the bone to regrow cartilage), but as the season with the Dodgers progressed the body part had become less and less of a concern. A shot of Synvisc (helping lubricate the shoulder joint) in spring training had helped the recovery process, leading to a fully-functioning throwing arm come September.

Six years later, Drew reports that he's still had no problems with the shoulder.

"I was a year removed from surgery, but I was throwing out runners at the end of the year," he said. "I'll be completely honest, my right shoulder to this day feels great. But my left shoulder still hurts (due to bone spurs suffered in '11)."

Following the examination by the Red Sox medical team, and subsequent disagreement between parties, Drew set off to find some clarity regarding the situation. He visited a series of shoulder specialists, including Dr. James Andrews.

"It was frustrating because you had one doctor say, 'Look, I've seen 100 times worse shoulders. Is J.D. going to be able to play for you? Absolutely. Is he going to be in a position where he can't perform five years down the road? No way.' We had to be careful to word the contract that if I got injured playing for the Boston Red Sox it was viewed as different than me being injured before," Drew said.

"I never felt like Theo didn't want me. It was well known the Red Sox wanted me to play in Boston. It wasn't like, 'We trust our doctor and there is no way we're bringing this guy in here.' They were basically saying, 'Just give us some assurances if something happens with this injury you had we're going to be able to address that for the sanity of ourselves, our team and our fan base.'"

Yet, despite the wait and the drama, Drew never grew concerned that his five-year, $70 million deal was in jeopardy. And at the end of the day all that changed was a clause that stated that the Red Sox could have voided the fourth or fifth years of his deal if time was lost due to the preexisting injury in the third or fourth season.

"I don't ever remember being overly anxious," he said. "I remember being like, 'This is weird,' and then thinking that maybe I wasn't healthy. Scott was like, 'You need to see Andrews. We're getting second opinions.' I told him, 'I feel great, Scott. I'm not hurt at all.' I guess there were a couple of times I missed a little time and they documented it as, 'sore right shoulder,' instead of tired shoulder. I was still recovering from surgery. It was just a unique situation."

And now, it's Napoli's turn.

"I just know I was getting closer and closer to spring training and I was like, 'Who am I playing for?'," Drew said. "As a player you're conditioned to be a free agent, and it doesn't happen very often where you're coveted by a team to sign a nice deal. I'm sure [Napoli's] at home trying to get it all ironed out."