McAdam: Envisioning what a Xander Bogaerts contract might look like  taken at BSJ Headquarters  (Red Sox)

(Billie Weiss/Boston Red Sox/Getty Images)

The final week of the season contained plenty of speculation about Xander Bogaerts.

Would this be the final series in a Red Sox uniform? What would the fan reaction be like? What would management say?

Bogaerts understood the circumstances. When Alex Cora took him off the field with three innings left in Game No. 162, Bogaerts hugged some teammates, waved to the fans and tipped his cap.

Later, BSJ reported that Bogaerts had had multiple meetings with the team, attended by ownership, in the closing weeks of the season.

And with that, Bogaerts returned to his native Aruba for the winter, his status uncertain.

In another month, Bogaerts will almost certainly opt out of his current contract -- unless the Red Sox get him signed to a new deal before that.

By all accounts, Bogaerts would prefer to remain with the Red Sox, the only organization he's known. Even if there's some bruised feelings from the Red Sox' lowball offer last spring, the consensus is Bogaerts wants to finish his career with the Red Sox -- at the right price, of course. By the same token, the Red Sox -- from ownership on down -- have made it clear they will make retaining Bogaerts a priority.

"We want to keep him here for a long time,'' said president of baseball operations Chaim Bloom.

Less attention has been spent on what it would take to accomplish that, and eventually, the Red Sox are going to be put in position where they have to make a compelling offer to Bogaerts.

What will that look like? How long will the deal need to be and for how much?

That's where things get complicated.

First, the Red Sox need to acknowledge the obvious: they're going to have pay significantly more than the $20 million AAV of his current deal. The game's other top shortstops -- Corey Seager ($32.5 million AAV), Carlos Correa ($35.1 million AAV), Francisco Lindor ($34.1 million AAV) -- are all living in the $30 million AAV neighborhood. At some point this winter, Trea Turner will join them.

So, the first number on Bogaerts' AAV has be a '3.' if the Red Sox aren't ready to commit to that, then they're wasting everyone's time. They don't need to make Bogaerts the highest-paid shortstop in the game. It's unlikely that he'll top Lindor's number, or, for that matter, Correa's. The latter signed a one-year deal last offseason with Minnesota and will be joining Bogaerts in the opt-out line, looking for a much longer commitment.

But Bogaerts has to be among the top five highest-paid shortstops when all is said and done, because that's how the industry works: the money for elite free agents always goes upward. When Bogaerts signed his last deal, he took a significant discount in order to remain with the Red Sox. He has no reason to be so selfless again.

Compare WAR (as determined by Baseball Reference) over the last four seasons: 

Bogaerts -- 18.5
Correa -- 18.0
Lindor -- 14.6
Seager -- 12.8

The tricky part will be the length of the deal. The Red Sox will naturally want to limit the length of any offer as much as possible so as to reduce their liability as Bogaerts ages. Bogaerts turned 30 earlier this month and just experienced his best year defensively, having made some adjustments to his pre-pitch set-up to improve his first step and overall range. Amazingly, when it comes to defensive runs saved, this past season was his best (+4). That suggests, as Cora noted the day after the season, that Bogaerts is capable of playing short for several seasons to come.

Eventually, Bogaerts may need to shift elsewhere -- left field, first base, or DH. But not anytime soon. And even when he has to move, toward the back end of the deal, he can continue to provide value offensively.

A six-year, $186 million deal would be a good baseline -- with a seventh-year option and a buyout that would take the guaranteed money about $190 million -- seems to make a lot of sense for both sides.

That might not be a maximum-value deal for Bogaerts, which could alarm Boras. Then again, it will be a crowded shortstop market this winter, with Correa, Turner and Dansby Swanson in competition for big deals. It's not a given that Bogaerts could beat that elsewhere, especially with a number of teams either locked in to recent big-ticket free agents (Texas, Detroit, New York Mets) happy with their own young shortstops (Toronto, Tampa Bay, Kansas City, Houston, San Diego, Pittsburgh), expecting prospects to take over (Yankees, Baltimore) or incapable of spending at the top end of the market (Cleveland, Oakland, Miami, Cincinnati).

There remains a handful of teams who have needs at short and the wherewithal to spend -- Philadelphia, St. Louis, San Francisco and Seattle. And another few who could lose big-name shortstops of their own and be in the market for another (Los Angeles Dodgers, Atlanta, Minnesota).

The Red Sox would be well-served by making Bogaerts their last-best offer before the end of the World Series, after which Bogaerts can entertain other offers and have his asking price enhanced. If they make it worth his while, they can retain one of the game's best shortstops, one whom they already know can perform in Boston, and save themselves a lot of drama.

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