Ben Cherington

Boston Red Sox general manager Ben Cherington sits in the stands before a baseball game between the Boston Red Sox and the New York Yankees in Boston, Sunday, Aug. 18, 2013. (AP Photo/Michael Dwyer)

SAN FRANCISCO — If you had to pick one moment that divides the horror of 2012 and this year's beard-toting, division-leading rebirth of the Boston Red Sox, you'd have to choose the trade.

"Which trade?" Los Angeles Dodgers president Stan Kasten deadpanned this year during a visit to Boston.

He was being sarcastic, of course. Aug. 25, 2012, was the trade. The Sox moved about $250 million, a record for not only baseball but professional sports, and one that the Red Sox and Dodgers can celebrate together this weekend.

The one-year anniversary of the blockbuster just happens to coincide with the teams' Sunday night match-up on national television. The three-game series in Los Angeles begins Friday.

"It gave us an opportunity to kind of re-forecast what this year's team would look like," Red Sox general manager Ben Cherington recalled, "and what teams multiple years down the road would look like."

An unnecessary refresher: Adrian Gonzalez, Josh Beckett and Carl Crawford and Nick Punto were sent out of Boston along with $12 million, a relative pittance compared to the salaries dumped. James Loney, Rubby De La Rosa, Allen Webster — and the trivia questions, Ivan DeJesus Jr. and Jerry Sands — came back from the Dodgers.

No one moment can ever single-handedly transform a season, but a year later, the blockbuster looks good all the way around. The Dodgers entered Wednesday with 42 wins in their last 50 games — something that hasn't been done since 1942 — despite losing Beckett to season-ending surgery.

"I felt like at the time, I had a lot of respect for the players we were giving up," Cherington said. "Whatever happened in Boston, all the guys that went to LA I would have bet on, and would have bet on them succeeding and doing well. I liked them all personally. It wasn't about those guys. We were looking at a situation where, if we hadn't done it, we were going to be back scrambling again in the offseason to sort of try to fix things in the margins, and not be able to really reshape things."

Someone who helped put that deal together must have, at some point, considered its historical relevance. What Cherington and his Dodgers counterpart Ned Colletti orchestrated — with the help of many around them — is essentially unparalleled.

"I don't know, I haven't thought about it myself," Kasten said of the trade's historical standing. "I know it worked for us. But, what we are involved with is just a different paradigm economically. It was a match-up of two teams that were in different places on their development curve and had a need that corresponded. And that's what you need. I guess you could say the same thing about Florida and Toronto. When you have teams that are at opposite ends of their development cycles, you'll get the big trades, like the Toronto deal."

Yes, the Toronto-Miami trade that followed in the offseason brought a similar imprint: Mark Buehrle, Josh Johnson and Jose Reyes were part of a 12-player swap that moved around $150 million in salary to Toronto. But that wasn't quite to the scale of the original, at least in terms of dollars.

What about Cherington? He's a serious man, and seemingly always on the job. Has he paused for a moment, poured a beer and thought: 'Wow, we pulled off this trade?'

Nope.

"I've never done that," Cherington said. "The celebratory moments come after a big win or some team success. Because that one, there were so many people involved: baseball ops, scouts, front office people, ownership. So many people involved. We were happy, but I think both teams were happy. Both teams felt like it was the right thing to do for their respective situation, so it took a lot of work on both teams' part to get the thing done. So there was a sense of accomplishment, but we weren't — we were losing games. We sucked at the time. Nobody was cracking drinks."

The Red Sox and Dodgers are in first place. The Blue Jays are in last. One American League East team's mega-deal has worked thus far, and the other's has not.

Sox manager John Farrell took questions from an audience at a seminar this week, including one about the difference between the Blue Jays and Red Sox: specifically, whether Farrell had noticed a difference in how the organizations develop pitchers.

The big trades weren't a part of the question, but the answer provided big-picture relevance.

"We can have a seminar on this question — not just because it's Toronto and Boston," Farrell said. "There are very distinct differences and it starts, I think it starts, at the top. And the reason I say that: I found Toronto to be a scouting-based organization, which to me is on one plane, one-dimensional. You're looking at tools. Here, it's a player-development based system. It's the paths of the individuals that are running the organization. And that's not to be critical.

"We all know that there's three different veins in this game that people advance (through): baseball operations, scouting, player development. Well, in the player-development vein, you're going to look at things in three dimensions: mentally, physically, fundamentally to address and develop people, or develop an organization. I think as a scouting base, you go out and you evaluate the physical tools. And that's kind of where it ends, or that's the look at that time. That was my experience, that was my opinion."

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You knew this already, even if Farrell framed it nicely: the success of the Red Sox starts with Cherington. Boston's front office operates with a rare effectiveness. Farrell deserves heaps of credit, too, but he's been provided the right pieces.

That was your 2013 starting point, that trade. All the money the Sox were able to spend this offseason, all the good vibes of today— so much was made possible because of the salary shed. As assistant general manager Mike Hazen said, it was a "ripping-the-band-aid-off type of deal."

"The scope of the deal required that to be done on a number of levels," Cherington said. "Ownership was heavily involved with baseball ops and we were all dealing with our counterparts with the Dodgers. So there was a negotiation going on between two teams and a lot of it just was information gathering on both sides, trying to find out, 'Well, what would you be willing to do to fit your need?' That's atypical, just because of the scope of it. Obviously, the bigger the deal, the more money involved, the more ownership's going to be involved."

Cherington today is on his way to an Executive of the Year award, and that's why you should be at least a little weary of accepting the GM's assessment of his own negotiating skills.

"I think some people are better naturally at it than others," Cherington said, "and I would not put myself in that category. We have some others in the office that I think are naturally better at it than I am. I think you can learn it also. You can improve at it. It's like anything else: the more you do it, probably the better you get at it."

Hazen, for one, doesn't buy that: "He's being modest."

What does the art of negotiation mean for Cherington and for the Red Sox? In honor of the trade's one-year anniversary, here's a look.

YOU CAN'T BURN BRIDGES

It's not easy being a new kid. The younger generation of GMs have drawn the ire of the older crowd in the past. The stigma: they won't make trades, or they're always trying to a win a trade. Stoop kid's afraid to leave the stoop.

There's some truth here.

But why? The theory goes that less tenure equals less security which equals less willingness to go out on a limb. It's easier to be bold when you're Pat Gillick or Billy Beane or Brian Cashman, the guys who have done it a long time. The younger set has to worry more about public perception and about ownership, rather than focusing solely on their teams' needs.

"I think that happens," Cherington said generally. "I see more and more today, teams understand going into a trade discussion that it's not likely you're going to win, win, win a deal. You might win in the margins. It doesn't mean that it doesn't sometimes turn out that way: baseball's hard to predict. But every team has access to the same information, every team has smart people working for it, every team knows the value of players."

Regardless, Cherington clearly doesn't fit the stereotype. He's not afraid to take a plunge.

"No," Farrell said. "One, he's got a scouting background that enables him to use all approaches to evaluate a player. His personality is such that he includes others to have a voice and major decisions that are being made. Ultimately, he's the one that's going to make it and be responsible for it, but his leadership style is one that is very even-handed. It's emotionally controlled to where there's not knee-jerk reactions. He doesn't have a need to grab the limelight. He's a diligent worker, hard worker that is all about finding the best people available and surrounding himself with them. He's done a hell of a job in taking one situation and making changes to correct it as he sees fit."

The deals have to start somewhere.

Text messages, emails — these are all common ways to initiate trades these days. In effect, technology has made the trade process more efficient, but it hasn't changed the nature of the dialogue. The mediums are simply different.

"I still think it's the exact as it's always been," Hazen said. "It's easier to communicate without having to make 30 phone calls to 30 different GMs. Saves the GM some time in having to spend a lot of leg-work type stuff, and spend more time on the ones where there is genuine interest in certain things. That's probably helped define the focus when you're actually pursuing a deal or a particular team."

The brainstorming process is at least half the battle. Most of the time leading up to the trade deadline, for example, isn't spent haggling — it's spent finding a partner who is even interested in haggling.

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"Of course. Always, always," Hazen said of brainstorming proposals. "We spend days in that room (at Fenway Park ahead of the trade deadline) and kick ideas around, send email chains. That's all we do is kick ideas around: 'What about this, what about that? What about this guy, does that guy fit?' And then Ben can say, 'No, that's not a fit. No, he makes too much money. No, they probably wouldn't give him up — but I'll ask.' Sometimes we get those, and then he'll shoot, 'Yeah, that's an interesting idea. I'll see. Nah, he said no.' Alright, move on to the next one. And that's it, keep movin' on."

Cherington didn't recall a specific memory of the first trade he put together other than it was something on the minor-league side when he was the farm director.

What Cherington emphasized is that negotiating in baseball isn't the same as negotiating in other walks of life. Figure that a book or an audio CD on how to win every negotiation — the kind of thing they sell in SkyMall magazine on airplanes — wouldn't prove as useful to him as it may a vacuum salesman.

"In baseball, the unique thing is the world is so small, the universe of people is so small that you're dealing with," Cherington said. "If you go at it with an objective to win every negotiation at all cost, I'm not sure it works in the long run. Because you're going to have to negotiate something with the same person six months later, probably. How many agents are there? You have to talk to all of them. There's only 29 other teams. Everyone is looking to tilt the odds a little bit in their favor, obviously. But I don't think you see as much of a scorched-earth approach as in other industries really, other businesses, because it's such a small world. You can't burn bridges."

THE BOOK

The stereotypical offer-counteroffer banter that you may envision does not permeate trade talks as it does free-agency haggling.

"It depends on the circumstances, but often there's less back and forth (for a trade) than during a contract negotiation," Cherington said. "On trades, it's about the player, and everyone has their own idea of what the player's value, what they want to give up. Within a couple conversations, you can figure out whether this has no chance, and then you just stop talking. Or if it's pretty close, then you try to work it out. Whereas a contract negotiation sometimes can take lots and lots of conversations."

Cherington talked about the ability to improve as a negotiator, and the Red Sox take active, deliberate strides to that end. They actually take notes, be it on an agent or another franchise.

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Did you start high and brow beat your way into a better offer, or were you reasonable from the get-go? The Sox will remember, and they expect you to remember how they treated you too. Like Cherington said, it's a small world.

They keep a store of negotiating scouting reports, you could say.

"There are agents who develop sort of trends over time for their style and you take note of that, just like they take note of us too," Cherington said. "Every agent has a book on the teams and about how they do business. Same with other teams. We'll have notes about — in any negotiation we do, we keep notes, so that we know, we have some history for the style of back and forth. 'They said this, it means this,' and that type of thing. I think negotiating in baseball is a little bit different than other businesses because of the small world we live in, and also because a lot of the time, especially with trades, you know the goal really is to help both teams. If both teams prosper, then that's good."

Case in point, that Dodgers deal. Everyone's happy.

Farrell used the word "incredible" twice recently describing the blockbuster. Once was to describe his amazement that a deal of that magnitude came down so suddenly without leaking to the press.

The second time was to describe how the trade could look even better for the Sox in the future. If Rubby De La Rosa, who still could end up either a starter or a reliever long-term, and Allen Webster both pan out...

"This trade, I think it'll grow in importance the further we get down in the line," Farrell said, "and certainly if De La Rosa and Webster become mainstays here, then it's got a chance to be an incredible deal."

Cherington firmly said "no" when asked if he was at all nervous pulling the trigger with the Dodgers.

Let's double back then. Ben, are you sure you're not a good negotiator?

"I didn't say I wasn't a good negotiator," Cherington said. "I said there are other people in the office who are better than me. Who are more naturally inclined that way. Everyone has different strengths. I can do it, I don't mind doing it. I can do it plenty. I think if I was honest in myself in lining up myself in lining up my strengths, that wouldn't be at the top for me."

A lot of people will think differently this weekend when they see Adrian Gonzalez in Dodger Blue.

Follow MassLive.com Red Sox beat writer @EvanDrellich on Twitter. He can be reached by email at evan.drellich@masslive.com.