It would be so simple if Theo Epstein could do what his counterpart in New York, Brian Cashman, did last winter.

Figure out his team's deficiencies and pay to have them filled.

What the Yankees had going for them last winter was that three players and $50 million came off their payroll at the same time - Mike Mussina ($11M), Bobby Abreu ($16M) and Jason Giambi ($23.4M).

Enter CC Sabathia, Mark Teixeira and AJ Burnett, who combined to make, believe it or not, only $1.5 million more, combined, in 2009 than the guys they replaced.

The Red Sox, as we speak two days after the apocalypse (aka the 27th World Series title for the Yankees), have only one potential opening in left field as Jason Bay has filed for free agency.

They also have an opening at shortstop.

And free agency isn't as ripe as it was a year ago. One potential replacement, Abreu, re-signed with the Angels yesterday.

That means Matt Holliday, who hit .313 with 24 homers and 109 RBI with the A's and Cardinals appears to be the best player available.

In other words, fixing the Red Sox, if that's indeed what needs to be done, will not be an easy chore for Epstein.

Add in the fact that the Yankees won the World Series.

Hall of Famer and Red Sox analyst Dennis Eckersley pondered some of the decisions that lie ahead for Epstein.

"I wouldn't want to be Theo," said Eckersley. "There are so many question marks. I thought the Red Sox were the best team in baseball when they broke camp. But they obviously have some issues. I think this is going to be an interesting winter around here, almost as interesting at the season."

It may mean eating a big contract. It may mean trading one or two young players on the major league roster.

Here six difficult decisions facing Epstein and the Red Sox:

1. Do you sign Bay?

The Red Sox can't afford to lose his production - 36 homers and 119 RBI - but at what price?

Do you pay Bay $60 million over four years? Would that even be enough?

The Red Sox can afford to pay whatever the price is, but will it hamper them four or five years from now.

2. Do you trade Papelbon?

One taker might be the Philadelphia Phillies, who are bordering on desperate to bring in a big-time closer. Brad Lidge blew 11 saves, which is six or seven above the acceptable level.

Could he get the Red Sox a player like Jayson Werth (36 homers, 99 RBI), who is on a par with Bay?

This trade begs another question: Is Daniel Bard ready to be a closer for a World Series contender?

3. Do you trade Clay Buchholz?

This is probably the easiest question to answer: Yes.

Buchholz will be the No. 3 or No. 4 starter next season if he's here. He would have to be part of any package that would attract a big-time hitter (San Diego's Adrian Gonzalez) or big-time pitcher (Toronto's Roy Halladay or Seattle's Felix Hernandez).

The fact that Buchholz went out with a decent bang - five innings, two runs allowed against the Angels in the American League Division Series - might help his value.

But Buchholz is young, cheap and under their control for five more seasons. That is a valuable asset.

Do the Red Sox trust Daisuke Matsuzaka to be a No. 3?

4. What do you do with Lowell and Ortiz?

Both could rebound big in 2010. But both could repeat 2009, which would probably spell doom.

Each is scheduled to make $12 million next season and neither is a trade asset.

Do the Red Sox eat one of those contracts so as to allow the Red Sox to trade for a first baseman (Gonzalez in San Diego) and move Kevin Youkilis to third base? Then Lowell or Ortiz would become the official designated hitter.

5. What about shortstop?

Is Jed Lowrie ready to become the everyday shortstop for a World Series contender?

Is Alex Gonzalez's defense, which is very good, good enough to make up for his inconsistent offense?

This position has been a big problem for Epstein to figure out since he replaced Nomar Garciaparra.

Maybe it's time to bring back Orlando Cabrera, who seems to have a way of injecting life into the franchises he joins, most recently the Minnesota Twins. One issue is he turned 35 on Nov. 2 and he committed 25 errors in 2009.

6. Do you re-sign Josh Beckett?

Another very difficult question. He is not going to take a discount. He did that when he foolishly signed the three-year, $33 million extension before the 2007 season.

Beckett is going to command/demand upwards of $100 million over five years.

Would you do it?

Or would you trade for Hernandez or Halladay, possibly giving up Buchholz and Bard, and give either of them that $100 million?

Maybe Eckersley is right. Maybe the real season has really just begun.

E-mail Bill Burt at bburt@eagletribune.com.