By Jeff Louderback

Ben Cherington has a tough job as general manager of the Boston Red Sox, and his responsibilities will only get more challenging when the regular season reaches a merciful conclusion.

The Red Sox have fallen out of contention, and it will mark the third consecutive season they have not reached the playoffs. As each day passes, it is becoming more apparent that Boston will finish under .500 for the first time since it wrapped up 1997 with a 78-84 record.

Those factors alone will escalate the pressure on Cherington, who is in his first year as general manager after serving in a myriad of front office roles dating back to the Dan Duquette era. Losing is not tolerated in Boston, especially after two World Series titles since 2004.

As part of the demands to build a winner again right away without enduring a so-called “bridge year,” Cherington has difficult decisions to make regarding the 40-man roster. To provide a glimpse of what Cherington will encounter when the off-season arrives, let’s play armchair general manager and determine what the 40-man roster might look like heading into the winter meetings, when players that teams want to protect from the Rule 5 Draft must be placed on the roster.

Also keep in mind that players who are on the 60-day disabled list do not have to be placed on the 40-man roster during the regular season, but they must be put on that list in the off-season.

Players who do not have enough service time to become arbitration eligible get a minimum salary which starts at $480,000.

Here are the decisions facing Cherington for the 40-man roster in the off-season (and their 2013 salaries; and listed by position):

Starting Pitchers (8)

1. Jon Lester, LHSP, $11.63 million
2. Felix Doubront, LHSP, min
3. Drake Britton, LHSP, min
4. John Lackey, RHSP, $15.25 million
5. Clay Buchholz, RHSP, $5.50 million
6. Rubby De La Rosa, RHSP, min
7. Steven Wright, RHSP, min.
8. Stolmy Pimentel, RHSP, min.

Lester, Buchholz, Doubront and Lackey will likely compose four-fifths of the 2013 Red Sox rotation. Of course, Cherington will pursue a frontline starter this off-season – maybe a trade for Seattle’s Felix Hernandez or signing Tampa Bay’s James Shields to a free agent deal if the Rays decline his 2013 option. Lester or Doubront could be packaged in a trade for a frontline starter.

De La Rosa is the highly regarded starting pitcher who has rebounded from Tommy John surgery and can hit the high 90s on the radar gun. He will be the player to be named later in last weekend’s blockbuster trade between the Red Sox and Dodgers. If De La Rosa is not packaged for an ace like Hernandez, he has a chance to make Boston’s 2013 opening day rotation.

Wright is the knuckleballer that the Red Sox acquired from Cleveland for Lars Anderson. Former Major League knuckleballer Tom Candiotti, who has worked with Wright, says the 28-year-old right-hander who throws a high 80s fast ball and a hard knuckler is about Major League ready. He is currently in Pawtucket’s rotation. He must be placed on the 40-man roster to protect him from the Rule 5 Draft.

Pimentel is one guy who could be removed from the 40-man roster. The former top prospect is still just 22, but his development has stalled at Double-A Portland.

Relief Pitchers (15)

1. Andrew Bailey, RHRP, arb. eligible, $3.90 million in 2012
2. Daniel Bard, RHRP, arb. eligible, $1.61 million in 2012
3. Alfredo Aceves, RHRP, arb. eligible, $1.20 million in 2012
4. Junichi Tazawa, RHRP, min
5. Mark Melancon, RHRP, min
6. Clayton Mortensen, RHRP, min
7. Chris Carpenter, RHRP, min
8. Alex Wilson, RHRP, min.
9. Josh Fields, RHRP, min.
10. Brock Huntzinger, RHRP, min.
11. Scott Atchison, RHRP, arb. eligible, $510,000 in 2012
12. Franklin Morales, LHRP, arb, $850,000 in 2012
13. Craig Breslow, LHRP, arb. eligible, $1.80 million in 2012
14. Rich Hill, LHRP, arb. eligible, $730,000 in 2012
15. Andrew Miller, LHRP, arb. eligible, $1.04 million in 2012

Tazawa, Mortensen, Morales and Miller have emerged as reliable arms in 2012. Miller could be a trade or non-tender candidate because he is arbitration eligible and the Red Sox have left-handers Breslow, Hill and Morales.

Carpenter, the hard-throwing righty that Boston received from the Cubs as compensation for Theo Epstein, has a strong chance of making the Red Sox bullpen out of spring training. He has been impressive at Pawtucket.

Melancon has been a disappointment after being acquired from Houston for Jed Lowrie and Kyle Weiland. He could be traded in the off-season to free a spot on the 40-man roster.

Bard is also a trade candidate with the thinking that he could benefit from a change of scenery. Recent media speculation had him going to Toronto this off-season as compensation for manager John Farrell if the Blue Jays do not sign him to an extension beyond 2013.

With his recent outburst and subsequent suspension, and Boston’s move to eliminate dysfunction for next season, Aceves could find himself traded.

Wilson, Fields and Huntzinger are all live arms that must be placed on the 40-man roster to be protected from the Rule 5 Draft. One or two could be included in a trade package.

Catchers (2)

1. Jarrod Saltalamacchia, arb. eligible, $2.50 million in 2012
2. Ryan Lavarnway, min.

The Red Sox could sign Mike Napoli, a free agent who can split time at catcher, first base and DH. There is also a chance that Boston will pursue Minnesota’s Joe Mauer, who would split time at catcher, 1B and DH as well.

Saltalamacchia is a trade or non-tender candidate because of his high pitchers’ ERA when he is behind the plate and his low on-base percentage and high strikeout rate at the plate.

Barring a trade, Lavarnway will make the opening day roster as one of the catchers.

Infielders (9)

1. David Ortiz, 1B/DH
2. Mauro Gomez, 1B/DH, min
3. Dustin Pedroia, 2B, $10 million
4. Mike Aviles, SS/IF, arb. eligible, $1.20 million in 2012
5. Jose Iglesias, SS, min
6. Will Middlebrooks, 3B, min
7. Danny Valencia, 3B, min
8. Pedro Ciriaco, IF, min
9. Ivan De Jesus, IF, min

Ortiz is on this list because the Red Sox will likely retain him at some point in November. Uber prospect Xander Bogaerts does not need to be placed on the 40-man roster, unless he is called up at some point in 2013. With his emergence as one of the top prospects in baseball and a future middle of the order bat at shortstop, defensive whiz Iglesias could be trade bait in the off-season.

Ciriaco and the recently acquired De Jesus give the Red Sox two quality utility infielders. Because of Ciriaco and De Jesus, and since he is arbitration eligible, Aviles could be traded or non-tendered.

Outfielders (7)

1. Jacoby Ellsbury, OF, arb. eligible, $8.05 million in 2012
2. Ryan Kalish, OF, min
3. Daniel Nava, OF, min
4. Jerry Sands, OF, min
5. Jeremy Hazelbaker, OF, min.
6. Ryan Sweeney, OF, arb. eligible, $1.75 million in 2012
7. Cody Ross, OF, free agent, $3 million in 2012

Ross is on this list because it is likely the Red Sox will sign him to an extension in the vicinity of three years and $27 million before season’s end or at least by November.

Like Aviles, it will be surprising if Sweeney returns to the Red Sox in 2013. There are too many other outfielders (who are either not on the 40-man roster but in the Red Sox farm system, or an outside acquisition) who can offer better production at an equal or more affordable salary (since Sweeney will get a raise).

The 25-year-old Hazelbaker was recently promoted to Triple-A Pawtucket and has a mix of power and speed. He must be placed on the 40-man roster to protect him from the Rule 5 Draft.

Overall Assessment

Free agents to be Scott Podsednik, Daisuke Matsuzaka, Aaron Cook and Vicente Padilla will probably not be brought back.

The Red Sox could also sign pending free agent James Loney, who is currently on the 40-man roster after his acquisition from the Dodgers. The aforementioned Napoli and right fielder/first baseman Nick Swisher are other potential signings for the Red Sox.

Outfielders Che-Hsuan Lin, reliever Pedro Beato and starting pitcher Zach Stewart are current 40-man roster occupants who are still under team control but will likely be dropped.

Aviles, Sweeney, Saltalamacchia, Nava, Pimentel, Atchison, Melancon and one of Miller, Hill and Breslow are expendable before or when 40-man roster space is needed because of free agent signings and trade acquisitions.

Forecasting the 40-man roster is not an exact science. As last weekend’s trade demonstrated, unexpected transactions can abruptly reshape the team. Expect the Red Sox to make upgrades to the starting rotation, first base and right field, and if they decide to move on from Saltalamacchia, a catcher to team with Lavarnway will be needed.