The top-five issues the Yankees need to address during the offseason

It was painful. Thursday night’s loss to Detroit in the deciding game of the Division Series was painful, not because the Yankees were blown away by the Tigers, but because there were so many wasted opportunities. Too many bases-loaded opportunities that were squandered by the ice-cold bats of Alex Rodriguez and Nick Swisher. For me, a 3-2 loss is way more devastating than a 10-1 loss.

All this aside, now that the Yankees’ postseason is over, they enter the offseason with more than a few pressing questions. Here are the top five issues the organization will need to address during the winter months:

1. Will CC Sabathia opt out of his contract and, if so, how much will the Yankees overpay for him?

My guess is that Sabathia is opting out. Why wouldn’t he? He surely would like to be making Cliff Lee money (thanks for continuing to screw us over, Cliffy). I heard some sports radio caller (a Yankees fan mind you) say that the Red Sox should make a move for CC. And they may, if only to drive up his price. But Sabathia and his family have supposedly really settled into the New York area. If he does bolt, it would be to the West Coast; however, it’s doubtful those teams will have the kind of money to entice him. The Yankees will most likely overpay and be saddled with yet another ridiculous A-Rod-like contract.

2. What about the rest of the starting rotation?

This was the same question that plagued the Yankees last offseason after Cliff Lee went to the City of Brotherly Love. While Ivan Nova had a very solid rookie season, it remains to be seen if he will progress or regress next season. Will Phil Hughes finally be healthy and live up to expectations? Will we be treated to more of A.J. Burnett’s head-scratching mound meltdowns? Do the Yankees take another chance on retreads Freddy Garcia and Bartolo Colon? My guess is that after locking up CC, they go after another free agent starter like C.J. Wilson (this way they can have the all initials rotation) or Mark Buerhle. Then there are the kids: Dellin Betances, Andrew Brackman and Manny Banuelos. It would be nice to see another prospect step up like Nova did.

3. Does Brian Cashman return as GM?

Cashman has said that he wants to return, but there’s always speculation he may need a change of scenery or he doesn’t want to work with a $200 million payroll and would rather be the GM who comes riding in on his white horse for the Cubs. Cashman held steadfast against the ridiculous contract for reliever Rafael Soriano (a battle he lost), but he also was throwing around ridiculous contract proposals for a disinterested Cliff Lee. I like that he was able to hold onto the Yankee prospects and had some great, unexpected success by getting the likes of Garcia and Colon. Of course, the way he handled the contract negotiations of Yankee Dynasty icons Derek Jeter and Mariano Rivera was abysmal and a total PR mess. Overall, I don’t know who’s out there who knows the inner workings and idiosyncrasies of the Yankees any better. I doubt Cashman is leaving the Bronx just yet.

4. What happens to Jorge Posada?

The catcher-turned-DH looked old for most of the season. Although he did pick up steam down the stretch and was one of the few hitters who actually performed solidly during the ALDS. A switch hitter, Posada was just awful from the right side of the plate and was later platooned. It would be nice if he retired and walked away from the game that seems to be rapidly walking away from him. Of course, if he wants to continue to play, Yankee fans may have to get used to the sight of one of the Core Four in a Seattle Mariners or Oakland A’s uniform. (Shudder … shudder.) The Yankees are going to have a plethora of DHs down the road (can’t wait to see A-Rod stepping up to the plate with his walker) so this is the probably the last time fans will see him in the pinstripes until a future Old Timer’s Day.

5. Where to play Jesus Montero?

Probably not the Yankees biggest concern, but Montero can indeed hit and seemed unfazed by the pressure of the playoffs. He is probably not ever going to be a big-league catcher (Austin Romine is being groomed to be the Yankees catcher of the future). There is talk of moving Montero into the outfield, and his defense couldn’t be any worse than Nick Swisher’s. (Yes, Swisher, whose contract is up, has improved, but still has the uncanny ability of turning a playable ball into a triple.) The Yankees need to find a way to get this powerful young hitter into the everyday lineup.