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Remembering when Red Sox traded their own big-name rental

Rob Bradford
July 18, 2018 - 10:54 pm

It's not a unique scenario. A big-name player in the last year of his contract dealt by a struggling team before the non-waiver trade deadline. Wednesday we saw it once again with Baltimore sending Manny Machado to the Dodgers for prospects.

So in light of the recent news of the day, it seems like a worthwhile exercise to reflect on the last time the Red Sox found themselves in the spot the Orioles found themselves. That would have been 2014 when they decided to move on from free-agent-to-be Jon Lester.

While the formula wasn't anything new -- one which saw a team try and get something for a player who was eligible for free agency at the end of the season -- there was something different about the Red Sox' trade with the A's. Rarely does a team trading the headlining player get an established major-leaguer back in exchange. It's not complicated. If a contending team is dealing for a useful addition, it probably isn't in any rush to extract talent from its roster.

But that was the case with outfielder Yoenis Cespedes going to the Red Sox in exchange for Lester and Jonny Gomes.

The A's offer of Cespedes was the only one presented to the Red Sox for Lester's services that involved a major leaguer heading back to Boston. According to major league sources, the most notable prospect the Sox could have secured was probably Baltimore's Dylan Bundy. (They weren't as high on Pittsburgh's Josh Bell as some.) But the Red Sox ownership preferred to sell this transaction not so much as the beginning of a rebuild as a perceived reload for the following season.

Get Cespedes, who had another year on his contract after 2014, and then make another run at Lester in free agency. On paper, not a terrible plan. But letting the longtime Red Sox see the outside world for the first time, albeit for a few months in Oakland, might have partially derailed the road to a return. It also eliminated the possibility of Lester hitting free agency with a franchise tag (always a deterrent for interested teams).

"My heart was still there even though I got traded, but when you’ve ground it out until that point and become a free agent you want to see what is out there. I feel like I still would have done that. I don’t know if the outcome would have been the same," Lester said prior to Tuesday's All-Star Game. "I think if you’re able to get to that point you kind of have to eliminate that at the end of the day. Even though I got traded to Oakland, it was still the unknown of another place. You still go back to the Red Sox and the known. All my buddies were still there. It’s a hard question because it’s the unknown of what if they didn’t trade me and if that would have changed anything. I don’t know.

"I still would have gone through the process. You don’t know if the teams would end up being the same because maybe the whole outlook of free agency would change. I would have had a qualifying offer hanging over my head. There are a lot of things that are factors in there that you probably can’t get the answers to without actually going through that scenario."

As was the case with Machado, the trade was hardly a surprise for Lester. He knew something was coming, so the pitcher was intent on making the most of his new situation. The lefty went 6-4 with a 2.35 ERA with the A's (who were eliminated in the Wild Card game), setting himself up for the six-year, $155 million deal with Cubs.

"I think it can be a really good positive sometimes," Lester said. "You get thrown in with a contender, that’s fun. Winning baseball games is fun. Playing for something at the end of the year is fun. And then you get a taste of it and maybe you like that organization, or maybe you don’t. And a guy like (Machado), he has never played for another team so maybe that’s an eye-opening experience.

"I couldn’t have gone from a further place from Boston, as far as media coverage and everything in baseball as I did in Oakland. I think there are just a lot of factors to narrow down to answer that question (if a trade impacts decisions in free agency). But I think once you’re a free agent you’ve kind of earned that right to be in that position, you should take advantage of it."

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