BOSTON (CBS)  – Ben Cherington has a full “to do” list now that he is general manager of the Boston Red Sox.

Aside from finding the right manager to lead the team, he has many question marks surrounding free agency, something that has been a thorn in the Red Sox’ side for the past few years.

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“Not good enough,” Cherington said on Tuesday when asked about the team’s recent track record in free agency. “It’s an area we need to get better at.”

The Red Sox have spent plenty of money the past two seasons, but have gotten little return from it.

John Lackey inked a five-year, $82 million deal before the 2010 season, and has gone 26-23 with a 5.26 ERA. He now needs to undergo Tommy John surgery and will miss the entire 2012 season. Carl Crawford hit just .255 after signing a seven-year, $142 million deal with the Sox last winter.

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While spending more wisely will be at the top of Cherington’s list, so is retaining a few of Boston’s own free agents. Closer Jonathan Papelbon and DH David Ortiz are both looking for new deals, and the new Sox GM would like to have them back if the price is right.

“We’d like to have both of them back. We’re going to have to see if there’s a contract that makes sense for them and for us, but we’d be a really good team if we could have both of them back,” Cherington said. “We’ve had initial dialogue with both.”

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Aside from Ortiz and Papelbon, Jason Varitek, Tim Wakefield, and JD Drew are all free agents. It seems as though Drew will retire, giving the Sox a hole in right field. That is one the team can fill internally with Ryan Kalish or Josh Reddick, who Cherington mentioned Tuesday, or seek the help of someone on the market. Cherington also said he would like to add a right-handed bat to help the outfield.

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Short stop Marco Scutaro has a mutual option with the team, and Cherington will also have to deal with arbitration with Jacoby Ellsbury, Daniel Bard and Jarrod Saltalamacchia.

With Lackey on the shelf for the season, and Diasuke Matsuzaka’s return unlikely until after the All-Star break, Cherington admits there is a big need for pitching, both in the rotation and in the bullpen. Again, that is a problem they could address internally or by signing another starter or two.

“We need to build some pitching depth,” he said. “We have talent in the bullpen. Obviously with Papelbon, not knowing the outcome of that, we could potentially have an opening at closer. We have a couple of players in-house we think are capable of filling that role if needed. But we need to add some pitching depth.”

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While it’s doubtful the Red Sox will go after big name pitchers like CJ Wilson of the Rangers, and possibly the Yankees CC Sabathia, look for them to search the bargain bin and hope to get lucky again.

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“I think most likely we’ll do that through some good creative, perhaps buy-low acquisition,” said Cherington. “We’re going to do our diligence on every available player. I think we need to hit on some pitchers this offseason in much the same way we did with Alfredo Aceves last offseason. We need to continue to do that.”