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These contract extensions aren't easy decisions. Just ask Dustin Pedroia

Rob Bradford
December 18, 2018 - 10:47 am

The Red Sox used to make a living off locking guys up early.

Josh Beckett in 2006. Dustin Pedroia twice. Jon Lester. Kevin Youkilis. And on a much smaller scale, Christian Vazquez committed to his three-year deal with a club option that wiped out two years of arbitration-eligibility.

It's also something the Red Sox have attempted to do with the likes of Xander Bogaerts and Mookie Betts in the last few years. Why? Because the closer a player gets to free agency the more expensive it usually gets for the club, and now both players are on the doorstep of the open market, with Bogaerts in his final year and Betts up after 2020. Yet as we sit here no long-term commitment has been struck.

Understood. It is, after all, perhaps one of the trickiest decisions a young player can face. Just ask Pedroia.

"I know at the end it’s going to be a very rewarding decision, but, dude, it’s not fun," said the Red Sox second baseman. "You think any of our guys want to leave a place they’ve been their entire career to go somewhere else? No, they don’t want to do that. But if they have to then they do it."

Pedroia's decision to ink an eight-year, $112 million deal back in 2013 was the second time he showed such a commitment to go that route, having inked a six-year, $40.5 million contract after his second full season in the majors. 

But while Youklis and Lester each took the same road as Pedroia via their own extensions, another guy all three players came up with, Jonathan Papelbon, chose to go year to year all the way up to getting his free-agent deal with the Phillies. ("He wanted to go year to year," said Pedroia of Papelbon. "He wanted to. Everybody is different.")

Now comes the next wave of extension candidates. It's a group that represents some of the most game-changing decisions for the Red Sox in recent memory.

Does Pedroia talk to the players involved about the experience?

"Absolutely," he said. "All the time."

Does the second baseman expect the decisions to be easy for anyone, even with all the guidance? Absolutely not.

"All my teammates ... Now that I’m a little bit older, I understand the business of the game. I want every one of my teammates to make the most money possible for their family, and I hope it’s in Boston. I really do," Pedroia said. " I pray it is because I love every single one of my teammates. But the reality is that it doesn’t happen anymore. They have to do what is best for them and their family. If guys leave, I don’t hold grudges. I’m not going to be like, ‘Man, that guy took the money …’ Hell, no.

"But I know all the guys who are on our team are loyal. They will do anything for any of us. That’s built into all of them."

But make no mistake about it, there is a loyalty to the team, and also a responsibility to each player's future and family. That's when it becomes clear that every situation is different, a reality Pedroia represents.

"I liked where I was," he noted. "Being a Red Sox to me means a lot. They’re the team that drafted me when everybody else could have but didn’t. I want to play for one team. That was it. I wanted to be there."