White Sox turning corner, but how sharp will that turn be?

As Winter Meetings approach, White Sox entering key next phase of rebuild

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The White Sox are turning onto that road of rebuild intrigue, the next-step phase where seeds germinating in fertile ground heighten expectations.

What should we expect at the Winter Meetings in San Diego next week, which might provide a clearer picture of where the Sox are headed in 2020? The long-term picture beyond next season is brighter after Seven Straight Squandered Seasons, that four-s acronym the organization is sick and tired of reading about. To what degree the Sox surround an up and coming young talent core with proven, more expensive quality will put next year in much better focus.

This much is known: Fans have grown weary of bad baseball. General manager Rick Hahn, vice president Ken Williams and manager Rick Renteria say they have, too. Hahn says chairman Jerry Reinsdorf, the man who controls the cash box, has as well.

But Hahn, his aggressive, $73 million, quick-strike move in the free agent market for catcher Yasmani Grandal notwithstanding and a $120 million, five-year offer for right-hander Zack Wheeler that was turned down, signaled a word of caution when he uttered an f-word win-starved fans don’t want to hear: five, as in years it might take before the Sox are seriously ready to call the rebuild complete.

“When we started off on this process [at the 2016 Winter Meetings] I was pretty candid that, in general, these things take about five years,” Hahn said at the General Manager’s Meetings in Scottsdale, Ariz., last month. “Our hope was that … we were going to beat that time frame. Some of the injuries along the way might have slowed us down. But we’re certainly not ruling out the possibility that this all comes together in a big way next season.”

The Sox can improve significantly from a 72-89 season and make it come together sooner rather than later by spending more and adding a starting pitcher or two, a right fielder, perhaps a designated hitter and bullpen help starting next week.

They’ve circled back to interest in Dodgers right fielder Joc Pederson, a former All-Star who hit 36 home runs in 2019, after a supposed trade fell through last spring. Pederson, a left-handed hitter who would add even more balance from the left side along with switch hitters Grandal and Yoan Moncada, also offers a needed defensive upgrade for a team that, at the moment, is lacking in the fielding department.

The most pressing need, though, is starting pitching, a commodity whose market heated up this week. While the Sox stepped up and signed Grandal to a four-year contract Nov. 11, clearing the club’s record $68 million (six years) for Jose Abreu by $5 million, with about $80 million currently on the books for their 26-man roster, they have more than enough to break another record without breaking their bankroll.

Whereas they were willing to offer Manny Machado $250 million guaranteed a year ago (and were outbid by the Padres), the Sox appear unwilling to pursue right-handers Gerrit Cole and Stephen Strasburg, the two most expensive free agent pitchers on the market, but they went hard in pursuit of their top free agent pitching target, Zack Wheeler, who took slightly less from the Phillies, $118 million and five years, than what the Sox offered. Cole Hamels, also courted by the Sox, signed a one-year deal for $18 million with the Braves.

For the Sox, $120 million or more for Wheeler would have easily more than doubled their highest outlay for a free agent pitcher -- $46 million over four years for closer David Robertson in 2014.

Left-hander John Dan that did nothing to alleviate Reinsdorf’s known disdain for long term deals for pitchers.

Perhaps Reinsdorf’s disdain for losing is even greater.

Stay tuned.

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