This Yankees offseason has no $189 million goal, nor does it appear a half-billion-dollar spending spree is in the offing, but the team will likely make a few moves. As always, we like to be helpful at ESPN New York, so once again we will aid the Yankees' decision-makers with a little game we like to call, "Spend Hal's Money."

Jon Lester

#31 SP
Oakland Athletics

2014 STATS

• GM32

• W16

• L11

• BB48

• K220

• ERA2.46

Today's Candidate: Jon Lester

Position: LHP

Age: 31 in January

Height: 6-4

Weight: 240

2014 numbers: $13 million salary, 16-11, 2.46, 219.2 IP, 1.10 WHIP

PROS: He is a top lefty starter at Yankee Stadium, which is always the right combination. He is championship-tested, even if he didn't come through for the A's in the wild-card game this year. He would fit in quite nicely smack between Masahiro Tanaka and Michael Pineda. If healthy, it would be an unbelievable 1-2-3 punch with Shane Greene, Ivan Nova and CC Sabathia, plus possibly Brandon McCarthy et al, making up a pretty solid rear of the rotation.

Lester is coming off arguably his best season in the majors, which has included many good ones. He basically throws 200 innings every season. All in all, he is an experienced top-of-the-rotation starter. There is a lot to like.

CONS: He basically throws 200 innings every season. He will move into his mid-30s during this contract. He will cost nine figures and probably want at least five years.

The Yankees have been down this path before. These large contracts that extend into a player's mid-30s are often bad toward the middle and end. Between Sabathia, Mark Teixeira and Alex Rodriguez, expectations will likely be dulled for the aging Yankees going into 2015. To continue this cycle has a definite downside because Lester may not age well in pinstripes.

THE VERDICT: Go for it. The Yankees should be in on Lester. They don't have to go crazy, maybe putting a five-year limit on their offer. If someone wants to be beat that, so be it.

Here is the thing, though, about the payroll. Hal Steinbrenner has said teams win the World Series paying less than the Yankees do. But if you want to make the playoffs every year, like the Yankees were doing before the past two blips, you can't really cut back.

You don't sign Lester to win a World Series, you sign him for a chance to win a World Series. You add Lester so your starting pitching is as deep as possible; if the offense can improve a bit, you can get into the tourney.

Starting Wednesday, two wild-card teams will begin play in the World Series. They deserve all the credit in the world, but there is no grand design to be mimicked. The Royals hadn't made the postseason since 1985, so, if you want to do it like them, Yankees fans can wait until 2041 after their own 29-year playoff drought.

The Giants are becoming championship regulars, and while they deserve praise, they have been very fortunate. They have been a 70-or-so-win team five out of the past 10 years. This season, they used the expanded playoffs to sneak in as the second wild card and then had none other than Travis Ishikawa hit the pennant-clinching homer.

The goal of the offseason is to try to give yourself the best chance. The Yankees have to be in on Lester, because he may be the free agent who can most help them return to the playoffs. They need to be in on him, even if they put limits on what they're willing to give.