Jon Lester remains the key to the free-agent market

SAN DIEGO – The Jon Lester sweepstakes are nearing their end, and as the lobby at these Winter Meetings on Monday night teemed with empty beer bottles and soused prognosticators, the parties involved waited, waited, waited, hopeful that their phones would ring sometime Tuesday with the news they desired.

What’s evident at this point, with the dollars rising and teams entertaining throwing in a seventh season that may be enough to sway him, is this: Lester has become the most sought after free-agent pitcher since CC Sabathia, and the teams left in the bidding – the Chicago Cubs, San Francisco Giants, Los Angeles Dodgers and, yes, Boston Red Sox, who indeed remained a viable option as of late Monday night – are primed to lavish him as such.

The ramification of Lester’s decision range far and wide, well beyond the teams involved, and the great thaw of 2014 started with the Lester decision seeming imminent. Oakland is nearing a deal that would send starter Jeff Samardzija to the Chicago White Sox for infielder Marcus Semien and a prospect package, launching the White Sox into immediate contenderdom and furthering the A’s overhaul. The other pieces on the pitching market, from lower-level free agents to the panoply of available arms on the trade block, will start moving as though in a game of speed chess.

Everything goes back to Lester and his choice, which is simultaneously enviable and excruciating. Each choice presents a great pro and con. The Cubs are familiar, thanks to their management, and scary, thanks to the necessity that their cadre of prospects hit in order for them to succeed. The Giants are winners, yes, and they’re also far from Lester’s home in Atlanta, where his wife and two young boys live. The Dodgers provide remarkable resources, but the geography doesn’t play, and they were late entrants into the game. And the Red Sox are like home, the organization that drafted, developed and nurtured Lester, but sore feelings from last year’s lowball offer that essentially prompted his free agency are understandable despite the team’s apologies in hopes of getting back in his good graces.

To each, Lester represents the best part of free agency: the instantaneous upgrade that costs only money. For a team like the Cubs, not having to dip into their well of prospects is of great value. They’re close to acquiring catcher Miguel Montero from Arizona, and the prospects they give up could amount to a rookie-ball kid and a relief pitcher – next to nothing with their current plan, which entails starting to win now, with new manager Joe Maddon and the arrival of future star Kris Bryant. The Giants don’t have the pool of players to get a Lester-like pitcher, the Dodgers are awash in cash, and the Red Sox find Lester a perfect player to complement their Hanley Ramirez-Pablo Sandoval triple play, which would preface a trade for another pitcher from their major league depth.

The free-agent market this season looks little like it will next year, when at this point an unprecedented number of top-level pitchers could hit the market. While teams will attempt to lock up some of the following pitchers, the 2015 Winter Meetings could have a docket that includes: David Price, Johnny Cueto, Jordan Zimmermann, Samardzija, Hisashi Iwakuma, Doug Fister, Rick Porcello, Mat Latos, Ian Kennedy, John Lackey, Mike Leake, Kyle Lohse and Bud Norris. That’s a baker’s dozen of pitchers who would command at least $30 million deals.

Such a flush market could lead to it working in the buyers’ favor … though this is baseball, and if ever there is a lesson to be learned, it is this: Free agency turns the rational irrational. Even for a pitcher like Jon Lester – a legitimate ace, a workhorse, a top-notch citizen – the bidding jumped to levels beyond what the Red Sox ever expected, more than double their $70 million offer last spring.

Perhaps he makes the final choice Tuesday, perhaps he delays it a bit longer, but the time is coming and Jon Lester is going to have a new team this week. They’re waiting, waiting, waiting, hoping, desiring, knowing that the vagaries of free agency will leave three losers and one winner happy as can be to spend at least $150 million.

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