Winter meetings: Can the White Sox crash the high-rollers table in Las Vegas?

All eyes will be on Bryce Harper and Manny Machado, who may be inclined to slow-play their hands

Today marks the eighth and final day of Hanukkah, but White Sox fans are still waiting for Hahn-ukkah to begin.

The winter meetings represent a big week for Rick Hahn, who has done everything he can to talk fans into the idea of the first White Sox megacontract since Albert Belle in November of 1996. A lot has changed in the 22 years since Belle signed a five-year, $55 million contract, and beyond the fact that $55 million in free agency barely clears the bar for a compensatory draft pick these days.

The New York Times’ story about the Sox’ newfound financial might back in 1996 reminds us that Belle signed at the height of Dennis Rodman’s powers.

”And I think when Jerry met Albert, the two of them felt very comfortable with each other,” Tellem said. ”And Jerry stressed to Albert that he’s had a lot of experience dealing with stars, not just in baseball, but in basketball, and that he would go to the end of the world to help protect him.”

As Reinsdorf said, ”The people of Chicago have shown in the case of the fellow with the pink hair that if you are playing for us, and you are playing your heart out, we’re going to embrace you.”

New York Times, Nov. 20, 1996

If the Sox are smart this week, they will disavow all knowledge of Bulls goings-on. Plausible deniability is on their side.

The next four days — OK, however long it takes for Bryce Harper and Manny Machado to determine a suitable offer — will define the White Sox for the next year.

That’s different from saying it’ll make or break the Sox. The Nationals missed the postseason in what people assume to be their final year with Harper, and the Orioles posted sub-.300 winning percentages before and after trading Machado. If the Sox are as flawed as they were last season, one player isn’t reversing the tide.

Still, landing a Machado or Harper is a landmark move in and of itself. It’ll not only show that the White Sox have the desire to spend like serious teams, but they can actually seal a deal like the big boys. That objective and talented third parties deem them a credible career choice.

If they don’t connect on a deal for either player, they probably won’t have a way to change minds about the rebuild until at least midsummer. Yasmani Grandal and Michael Brantley are fits and can help, but the Sox have signed second- and third-tier free agents before, and they’ve also whiffed on plenty of them. They require some level of finger-crossing, as will the progress of Yoan Moncada, Reynaldo Lopez and friends. Fast starts will be welcome, but mid-June is probably the soonest things can start to actually feel substantial.

The latter scenario is probably the more likely outcome, given the 100 losses and 10-year playoff drought. Hahn says that free agents understand the appeal of Chicago and understand which way the arrow is pointing, but the Sox still seem most useful as leverage for other teams given the seriousness they project. Still, there’s reason to dream, and unlike the outfielder pool a few years back, the Sox aren’t soft-pedaling their interest this time.

What does it look like now?

Ken Rosenthal advises everybody to not overlook the swordfight between agents. Scott Boras (Harper) and Dan Lozano (Machado) are going to be angling for making the most out of a superstar in his prime, including signing the biggest deal for the highest annual value. The first contract could dictate the second, so the winter meetings may not be able to contain the standoffs:

The prevailing assumption in the industry is that Boras wants to set new benchmarks with Harper’s free-agent deal, whether in total guaranteed salary, average annual value or — preferably — both. Therefore, he will want Machado to sign first, securing the negotiating equivalent of “last licks,” in which he would step to the plate knowing the number to beat. Boras’ track record also indicates he would be willing to go to extra innings, moving at his own pace, stretching talks into January, if necessary.

Machado, though, is not necessarily going to come off the board quickly. As I reported on Saturday, it’s not just the Phillies, White Sox and Yankees that are pursuing him. One rival executive hears at least three other teams are in the mix and will meet with Lozano at the meetings. What is not known: Whether Machado has met personally — or when he will meet — with interested clubs.

Sleeping dogs could have a lot to do with how Harper’s courtship plays out in particular.

The Nationals seem to be out on Harper, as Washington’s principal owner Mark Lerner said about the offer Harper rejected, “This is the best we can do.” However, Buster Olney says it’s still hard to count them out.

While the Cubs have stopped short of such finality from their top brass, Theo Epstein has downplayed his financial flexibility so far this winter. But here, MLB Network’s Dan Plesac told Bruce Levine he senses the Cubs could make a serious play by offering a shorter deal with a record-setting average annual value.

If something like that happens, then you have to file that under “victors/spoils” and hope that the core sells the next megastar on better times ahead. Then again, maybe Machado will then be content to win the total contract value battle, and both headliners can get a different line to tout.

Take a second to support Sox Machine on Patreon
Jim Margalus
Jim Margalus

Writing about the White Sox for a 16th season, first here, then at South Side Sox, and now here again. Let’s talk curling.

Articles: 3914
21 Comments
Oldest
Newest Most Voted
Inline Feedbacks
View all comments
MrTopaz

Meanwhile Reinsdorf is looking right at Machado and Harper like “Play for me, and I’ll make sure you get in the Hall of Fame NO MATTER FUCKING WHAT.”

Double_Dog

Oh holy hell that’s funny…laughed out loud for about nine seconds (which in reality is a long time to laugh aloud)

jorgefabregas

Unless you’re Albert Belle

joewho112

Look at how we treat stars in Chicago [points to Jimmy Butler and Jay Culter]

Josh Nelson

Let’s get people excited this Monday morning

andyfaust

I’d be as thrilled as anyone if they could sign him. Partly because of what he could add to the rebuild but equally because of how badly it would upset so many Sox haters that feel compelled to take shots at the Sox when tweets like this one go up.

Josh Nelson

Cubs fans will be salty.

AirTrafficAJ

Which will inevitably end with “yeah but nobody goes to THE DOWN ARROW attendance attendance attendance hurrrr durrrrr”

dongutteridge

As Harper does as instructed by Boras. Make every team think you’re interested in playing there. In the end, more millions from Philly!

Patrick Nolan

I feel like Grandal and Brantley are a cut above anyone the Sox brought in last time.

Right Size Wrong Shape

Grandal yes, but factoring in Brantley’s injuries I don’t know that he’s any more valuable than Melky.

GreatjonHumber

he played a full season last year at a high level, it’s the kind of risk we need to be willing to take if this thing is going to work.

35Shields

A pretty high bar to limbo under…

Josh Nelson

Rob Bradford from WEEI wrote a story about Joe Kelly this morning, and is now reporting that the White Sox have strong interest in Kelly.

Link to article: https://weei.radio.com/blogs/rob-bradford/red-sox-competition-joe-kelly-coming-focus

35Shields

But y tho?

PopeDonnPall

Joe Kelly is an upgrade in our pen – no doubt. But what the heck good was stockpiling bullpen arms via trades and international money and draft if not to avoid having to spend big money on Joe Kelly types until we are ready to win. I’d rather it go to starters and position players. It’d be disappointing if we can’t piece together 4 pen pieces by the time we’re contending from the pool of:

Zach Burdi, Carson Fulmer, Ryan Burr, Aaron Hamilton, Jace Fry, Caleb Frare, Thyago Vieira, Dylan Covey, Nate Jones, Kodi Medeiros, Jose Ruiz, Jordan Stephens…

Trooper Galactus

There’s something to be said for depth, being able to extend service time on some of those guys because an incumbent is legitimately blocking them, and having a potentially decent trade asset if things break right with him and the prospects behind him. Certainly, Kelly isn’t looking at a David Robertson-type payday like a few years ago.

As Cirensica

I am ready to move on from the narrative of signing players in the hopes we can trade them to the narrative of signing players to win games.

zerobs

Joe Kelly is a walk machine. Avoid him like the plague.

denbum

Meanwhile, Omar Vizquel gets a promotion. Don’t have much to go on, but the smell test says he may be the one in-house candidate being groomed to take over the reins from Renteria.
Doesn’t seem to be any issue with Sox bloggers on the “keep / replace manager” debate. Count me in on the organization putting in place the mgt/coaching team to accelerate this rebuild. Might be time to invite discussion on this? Question may be so Sox look for retreads like Girardi, Scosia, et al. or start a new chapter such as Vizquel or the likes.

35Shields

Does this mean that Jirschele is moving up to WS?