Early offseason rumors point to aggressive and potentially pricey winter for White Sox

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Rick Hahn has declared that his front office will once again be aggressive this winter as the White Sox move toward the contention phase of his rebuilding project.

So it wasn’t exactly shocking to see the White Sox mentioned multiple times in the monster offseason primer ESPN’s Jeff Passan unleashed Wednesday.

Fans will surely latch on to the White Sox getting mentioned among the myriad teams expected to pursue Gerrit Cole, the Houston Astros’ All-Star hurler who will be the top prize on this winter’s free-agent market. Of course, a certain segment of fans latched on and still haven’t let go of the team’s failed pursuits of the top prizes on last year’s free-agent market, Manny Machado and Bryce Harper.

Regardless, Passan did include the White Sox as one of nine teams — roughly a third of the league — “positioned and motivated to explore adding” the Cy Young candidate.

It could potentially be argued that the White Sox don’t desperately need another arm added to a rotation that already has four spots spoken for (Lucas Giolito, Reynaldo Lopez, Dylan Cease and Michael Kopech) and will be awaiting the healthy returns of several candidates for the fifth spot (Dane Dunning, Carlos Rodon and Jimmy Lambert).

But while that might sound like plenty of starting-pitching options, Hahn has made no secret about starting pitching’s prominent place on his offseason to-do list. That stems from the organization’s major league ready depth getting worn bare early on in the 2019 campaign and the ensuing parade of mostly ineffective fifth starters both before and after Rodon’s Tommy John surgery.

While there’s a possibility that adding an increased amount of bottom-of-the-rotation depth is what Hahn means when he talks about a desire to add starting pitching this winter, it would not be a surprise to see the White Sox try for a top-of-the-rotation, impact pitcher, too. Cole fits that bill better than most of the pitchers in the game, and in bringing him to the South Side, Hahn could add a great deal of stability to a rotation full of young arms, provide depth by bumping a couple of those promising young pitchers down toward the bottom of the rotation and import the big-time player from outside the organization that would kick the rebuild into overdrive.

Of course, that is easier said than done. Hahn has said that the White Sox financial flexibility created throughout this process will be utilized to bring in free agents, but that same segment of the fan base still stewing from how things played out with Machado won’t believe him until he proves otherwise. Hahn realizes that and has said so on multiple occasions.

Will Cole be the free agent that allows Hahn to dispel of the narrative that the White Sox won’t pay for a top-of-the-line free-agent addition? As Passan mentioned, Cole’s expected to have plenty of suitors. He’s also expected to command a gargantuan payday. If the White Sox can get him to buy into the organization’s bright future and outbid the field, they could add a transformative figure to the mix and really crank up expectations for 2020 and beyond.

But it’ll cost them.

In addition to listing the White Sox among the interested parties in the Cole sweepstakes, Passan mentioned another potentially pricey route the team might go in trying to build a long-term contender: extensions.

Early contract extensions were all the rage earlier this year, drastically reshaping the still-to-come free-agent market months before it even got started. The White Sox were part of that trend, inking Eloy Jimenez to a multi-year contract at the tail end of spring training that wiped away any service-time concerns and allowed their prized prospect to start his rookie season on Opening Day.

Well, Passan hinted that they might aim to do that sort of thing again before the 2020 season starts. No, not with Luis Robert, who is facing similar service-time questions to the ones that accompanied Jimenez through the winter. Passan listed Giolito and Yoan Moncada among players to “keep an eye on” when it comes to offseason extensions.

Certainly that sounds like something the White Sox would like to do, that any team with young players performing as well as those two have during the 2019 season would like to do. After brutally disappointing 2018 seasons, both transformed their games in the offseason and have come out of it showing why they were both, at one point, ranked among the top prospects in baseball.

The 25-year-old Giolito has gone from allowing more earned runs than any pitcher in baseball last season to an All Star and the ace of the starting staff in 2019. After a second straight strong outing against the high-powered Minnesota Twins on Tuesday, he’s got a 3.20 ERA with 203 strikeouts in 157.2 innings this season.

Moncada is 24 and in the midst of an excellent season that’s seen him go from 217 strikeouts to the team’s best hitter. He came into Wednesday night slashing .297/.353/.540 with 22 home runs and 63 RBIs in 102 games. He might have less of an incentive to sign a long-term deal right now considering the $31.5 million bonus he got when he signed with the Boston Red Sox back in 2015.

The White Sox have a pretty good track record when it comes to extending their own players. But like with adding someone the caliber of Cole, adding two more long-term deals to the books would be a pricey endeavor. That being said, it could end up saving them money by bypassing arbitration.

Passan’s primer is wide-ranging and covers other potential White Sox topics without mentioning the South Siders, specifically. There are plenty of other free agents who could wind up as targets of Hahn’s front office, like the top position player on the market, Anthony Rendon, or a guy who fits the Jon Lester, cherry-on-top-of-the-rebuild profile in Madison Bumgarner. Then there’s the trade market, which Hahn could explore in his quest to add that big-name player to push the White Sox over the hump in their transition from rebuilding mode to contending mode.

The White Sox once more plan to be aggressive, not deterred by the results of the Machado and Harper sweepstakes. Whether they’ll be able to convert this time obviously remains to be seen. But there’s no reason they can’t be in the mix once again.

Hahn, discussing the team’s financial flexibility in the wake of Machado’s decision to spend the next decade with the San Diego Padres, pledged that “the money will be spent.”

Well, if the White Sox are going to sign Cole or Rendon or Bumgarner or ink Giolito or Moncada to long-term extensions or do just about anything to radically improve their long-term fortunes this offseason, spending the money will be necessary. They seem ready for that, and their inclusion in these early offseason rumors sets the stage for another aggressive winter.

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