Jon Lester Revisited: Should Red Sox Go All-Out To Bring Back Ace?

Jon Lester In the words of the “Million Dollar Man” Ted DiBiase, “Everybody’s got a price.”

Jon Lester’s will be high.

Lester is hitting free agency at the perfect time, as the left-hander is coming off his best season to date. The question — the only question, really — is whether Lester’s price tag will be too high for the Boston Red Sox, who left the door open for a potential reunion after trading the veteran hurler to the Oakland Athletics at the Major League Baseball non-waiver trade deadline.

The Red Sox, in theory, could sign whoever they want this offseason. WEEI.com’s Alex Speier recently ran the numbers and concluded Boston will have at least between $50 million and $55 million to spend, though that number will fluctuate based on the organization’s other plans, including its willingness, or lack thereof, to spend beyond the $189 million luxury tax threshold.

It’s an enviable position, obviously, but it doesn’t mean Boston can go out and make it rain for everyone. If it did, the Red Sox could sign up for seven years of Lester, Max Scherzer and James Shields, deal for Cole Hamels and Johnny Cueto, and make a call to Jostens to be fitted for their 2015 World Series rings. Reasonably, the Red Sox are in a position to pursue a top-flight starter and a No. 2 while also taking care of their other offseason priorities.

Let’s make this clear. Re-signing Lester is the best means to obtaining a No. 1 starter. Lester has pitched like a legitimate ace this season, he’s in his prime and he’s a known quantity. Signing him also wouldn’t require the Red Sox to relinquish any assets, which is important because Boston could then use those assets for a separate deal geared toward landing a No. 2 or adding some “thunder” — to steal a phrase from David Ortiz — to the offense.

A line must be drawn in the sand, though. There are enough cautionary tales — CC Sabathia, Johan Santana, Barry Zito and even Justin Verlander, to name a few — to give reason for pause, though relying solely on history wouldn’t be fair to Lester or any other free-agent pitcher. There’s an unavoidable risk involved in signing any player to a long-term contract, so the decision, particularly for a big market team like the Red Sox, boils down to just how far one’s willing to go before packing up the chips and walking away from the table entirely. Having money to spend and actually spending it are two different beasts.

Should the Red Sox pay, say, $175 million over seven years for Lester? Absolutely not.

A $25 million average annual salary for Lester is reasonable if it’s attached to a four- or five-year deal. Once the commitment extends beyond that barrier, which is possible, if not likely, given recent market trends and overall demand, hitting the trade market becomes the more palatable move.

Sure, dealing high-end prospects stinks. But it’s a reasonable sacrifice for landing Hamels at $90 million over four years versus Lester at $175 million over seven years, mainly because those three additional years could wind up becoming dead money if Lester breaks down. A team like the Red Sox could absorb the back-end hit to some extent, but new needs that might require sizable financial commitments inevitably will arise. (After all, Ortiz isn’t going to play forever and the Red Sox won’t want to be too strapped financially beyond 2017, which is the second of two option years built into the slugger’s contract.)

So what then is “the line” for Lester? It’s impossible to say exactly because we don’t know the pitcher’s demands and/or other pertinent information, including the demands of other free agents. But going beyond five years and $130 million-ish would be risky.

The Red Sox have other chores this offseason, including re-signing Koji Uehara (or perhaps another closer), filling out the bullpen, landing a backup catcher and potentially pursuing a third baseman. Nothing is as important as building a strong rotation that currently features only two locks — Clay Buchholz and Joe Kelly — for the 2015 season; except filling out the unit with the right pieces.

Even DiBiase knows when to put his wallet away.