Presenting Brian Cashman's starting 5

NEW YORK -- The offseason is upon us. With Brian Cashman's new contract about to become official, he needs to get to work. Being the helpful sort, we at ESPNNewYork.com have laid out a five-point plan for the Yankees GM this winter.

1. Sign CC Sabathia at the right price

The Yankees are still trying to make Sabathia skip free agency, but rarely do players this close to seeing what the market could bring sign before listening to other teams. The Yankees will make an opening pitch to try to prevent Sabathia from opting into free agency. Both sides are highly motivated to get a deal done, which would prevent any drama.

Still, from Sabathia's point of view, there doesn't seem to be any harm in waiting and seeing. The Yankees are going to put forth an initial bid, which won't go down. If Sabathia truly wants to stay, he can always shop whatever offer is out there and make the Yankees match it. Business-wise, this is the best way to go. PR-wise, it may not be.

Sabathia has come across as the most sincere of Yankees. It is hard not to believe that he wants to stay in the Bronx.

However, when we asked him what LeBron James would do when he was a free agent, Sabathia said that James would take the most money. LeBron didn't, but Sabathia might have foretold his own thinking. Once free agency opens up -- no matter how many 10s of millions are being discussed -- feelings can get hurt and players can perceive disrespect in even luxurious offers.

What they should do: It would take major guts to let Sabathia walk. Yes, he didn't look great at the end of this year. His weight is a concern. If the Yankees get out now, their three-year deal that produced one championship and nearly 20 wins per season would be an all-time winner.

The Bombers have to offer Sabathia five years at $125 million and let him try to find six years someplace else. That is a substantial upgrade over his four years and $92 million. If Sabathia makes the Yankees go six years, they should eventually do it, but he'll have to force their hand.

If it is another seven years, they should let him walk and create a solid staff with a superior bullpen and offense.

2. Decide if Nick Swisher is the RF

The easy answer would be it is time for a change in right. Nick Swisher has been a very good regular-season player and a terrible postseason player, but the tougher question is: How would you replace him?

Carlos Beltran would come with more risk and possibly more reward. Beltran will be 35 next season and Scott Boras will likely want a two- or three-year deal. So that is more age in right, though the upside of Beltran's 1.302 OPS in 22 postseason games may make the gamble worth it.

Meanwhile, Cashman can just pick up Swisher's $10 million-and-change and get a .368 on-base percentage, 27 homers and 85 RBIs. Swisher is about to turn 31, so with a potential big payday waiting, the Yankees might want to keep him in right one more year.

Next year, maybe Swisher snaps out of being one of the smallest postseason players in history. So far, in 38 playoff games, he has a .169 average.

What they should do: Swisher is an asset. The Yankees could pick up his option and then work him into a deal for a starter. If they paired him with a pitching prospect or two, they might be able to add a young starter to their staff.

If there are no good deals, they should put him in right. If he's dealt, the Yankees could add someone like Michael Cuddyer, who has similar numbers to Swisher. Cuddyer has been better in the postseason, but we wouldn't give him more than two years. Cuddyer probably will get three.

This is why, ultimately, Swisher probably stays.

3. Go after C.J. Wilson, Hiroki Kuroda or make a trade

If Sabathia flees, then the offseason is going to be problematic. But let's say Cashman gets Sabathia back; his second starting pitcher signing will be just as important.

In the end, the Yankees would probably prefer Kuroda over Wilson. Kuroda wouldn't cost the dough that Wilson will. There is one catch. A source said that Kuroda wants to return to the Dodgers or go back to Japan. If this remains true, Kuroda is off the list.

The Yankees will have to be in on Wilson, but they are going to think long and hard about offering him five years at A.J. Burnett money ($82.5 million). Here is the catch: He may get more than Burnett.

So what do you get for that $16 million-plus per season? Over his past two years -- the only standout seasons of his career -- Wilson has averaged a 16-8 record with a 3.14 ERA. To have that for five years would be worth it. Wilson has never been great in the playoffs. But before Sabathia showed up in the Bronx, he hadn't done it in the postseason yet either.

There are some other starters the Yankees can try to sign. Names like Roy Oswalt, Mark Buehrle and Japanese standout Yu Darvish have some intrigue. The Yankees would have to win a posting fee to get Darvish and, though they like Darvish's skills, it is unclear how aggressive they will be in trying to secure his rights.

What they should do: Listen in on Wilson, but ultimately pass. He feels too much like Burnett. The money and years are too high for what he might be. He is 31, which isn't old, but the Yankees might assess him as a middle-of-the-rotation guy. Last year, they had Freddy Garcia for that and had to pay him only a $1.5 million base. Garcia finished 12-8 with a 3.62 ERA.

Better to bring back Garcia and try really hard to sign either Buehrle or Oswalt.

The Yankees can have the more seasoned kids (Hector Noesi, Adam Warren and David Phelps) in reserve from the start of the year. Meanwhile, Manny Banuelos and Dellin Betances can get more work at Triple-A and maybe could be midseason additions.

4. Explore a Jesus Montero trade

The Yankees loved what they saw from Montero in September. Right now, he has to be the favorite to be the backup catcher/DH. He should get a lot of at-bats.

But Montero boosted his trade value, so if the Yankees could deal for a legit No. 2/borderline ace like Matt Cain, then maybe Montero would go. Cain is a free agent after next year.

What they should do: Cashman has been willing to deal Montero before, but he was offered for Cliff Lee and Roy Halladay. Cashman wants a top-tier starter if he is going to give up Montero. The Yankees will at least listen.

5. Get a second lefty in the bullpen

The Yankees have paid a lot of money for lefty relievers who can't pitch. Even next season, Pedro Feliciano will pick up another $4 million even though he has never thrown a pitch for the team.

So Cashman will need to pick up a tag-team partner for Boone Logan.

What they should do: They should try to find some reclamation lefty projects. These seven-figure contracts have not worked out. Damaso Marte helped deliver the 2009 World Series, but barely pitched besides that October run. They should go cheap for Logan's sidekick.