The date is September 27th. The Red Sox don’t know it, but in less than twenty-four hours they will lose 4-3 to the Baltimore Orioles, completing the greatest collapse in baseball history. With the possibility of a one game playoff looming with Tampa Bay, and with Jon Lester set to take the mound for the final game of the regular season on short rest, Theo Epstein was doing his best to acquire a starting pitcher. And that should just about tell you everything you need to know about the 2011 Boston Red Sox. On the second to last day of the regular season there was no player in the organization outside of the starting rotation who the team felt comfortable starting in said theoretical playoff. No long reliever, no minor leaguer. With John Lackey’s elbow on the fritz, Daisuke Matsuzaka out of the picture, and Josh Beckett unable to pitch on one day’s rest (understandably), Bruce Chen was looking like Epstein’s best option. Bruce Chen. With that in mind, it’s a little easier to understand the strategies General Manager Ben Cherington has employed this offseason.

Heading into the winter, Cherington seemed to have a few easy moves to make. One, resigning Designated Hitter, David Ortiz, either through arbitration or a multi-year deal. (Ortiz is at least headed for arbitration, but a two-year deal is still not out of the question). Two, signing a reliable fourth starter to a short-term deal (think Hiroki Kuroda, Roy Oswalt, or Joe Saunders). Three, sign a solid right fielder to bridge the gap from J.D. Drew to Ryan Kalish and/or Josh Reddick (Carlos Beltran? Ryan Ludwick? Grady Sizemore?). Well, maybe these weren’t as easy moves as we thought. As of today, he’s done one of the three, that being locking up Ortiz. We’re not sure who will be the opening day right fielder yet for Boston. We certainly don’t know who will be slotted as fourth in the rotation. So where does that leave the team? Where does that leave Cherington? His acquisition of Andrew Bailey was big, Mark Melancon should be solid, Nick Punto figures to be a solid contributor. But what about right field? What about the rotation? Ryan Sweeny? Carlos Silva? Aaron Cook? Really? Yes, really.

The key to Cherington’s offseason comes down to this phrase: waiting game. In November, the price for Andrew Bailey was high. Really high. The Sox had been circling around him at the Winter meetings, but nothing came of it. Reports surfaced that the A’s were asking for top prospects in return for the electric young closer. Cherington didn’t bite though. With the market full of closing options, it was inevitable that some of them would have to come cheaply. In a game of bullpen musical chairs, Jonathan Papelbon, Francisco Rodriguez, and Heath Bell al found homes quickly. That left about three good relieving options for only two teams that were really looking for closers. What a difference a month can make. Cherington ended up dealing Josh Reddick, and two young prospects (who do have high upside, but certainly are not A level players in the organization) for Bailey. This is far, far less than anyone thought they could acquire Bailey for just four weeks earlier. By holding out, Cherington got his man, and got him without sacrificing important depth. (Remember that word, depth.)

It seems that the same strategy is being implemented in the search for a right fielder and a fourth starter. In early November, the Sox were looking at Kuroda, Oswalt, and Saunders. Care to guess three starting pitchers who are still currently unsigned? Kuroda, Oswalt, and Saunders. The longer Cherington waits, the cheaper these players become. All probably want somewhere between 10-14 million dollars a year, even for a one year contract. But, who’s to say that come mid-February, one of them won’t be desperate enough for a job that they would take a one-year, six or seven million dollar deal? The chances are pretty good that a solid option will still be available for cheap when the time comes. There are some downsides to this strategy. It’s quite possible that all three of these guys are signed within the next two weeks by other teams looking for extra starting pitching (and who’s not looking for extra starting pitching?). Cherington is standing pat though, he’s clearly determined not to exceed the luxury tax, which will reap benefits on the Sox in the future. On top of that, he’s not looking to overpay for players who don’t deserve to be overpaid. One or two million dollars doesn’t seem like a big deal now, but come July 31st, when Boston needs to make a trade, but can’t because they are one or two million dollars away from exceeding the luxury tax, this will make more sense. Every dollar counts, and Cherington is certainly counting to the last penny.

When the Red Sox signed Carlos Silva and Aaron Cook to minor league deals this past week (along with eleven other players), not much fuss was made. And that’s how it should be, neither pitcher has been of much value in the past. But, these are the moves that can make or break a season for a contending team. Cherington is building depth throughout the organization, something that was severely lacking last year. Everyone laughed when the Yankees acquired Bartolo Colon last winter, but it didn’t seem that funny come mid-July when the guy was a legitimate All-Star candidate. Both these players could amount to nothing (in fact, they probably will), but just the fact that the minors will be stocked with low risk pitchers like this is an enticing thought.

The waiting is the hardest part. There’s no doubt about it. Signing pitchers to minor league deals is boring. Waiting until February to assemble a team is boring. Saving money, prospects, and long contracts is not boring. Cherington and his team have a plan, they’ve had a plan from the first day of the offseason. And you know what? It’s starting to look like it’s working. It’s easy to have doubts about some of these moves. Some of them don’t seem to make a ton of sense. Just think back to the night of September 27th. Think back to Bruce Chen. Some things are worth the wait. Hopefully October baseball is one of those things this year.