The Jason J. Connor 2019 Winter Meetings Wrap Up: Chicago White Sox

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Overall, the 2019 MLB Winter Meetings, held in San Diego last week, will be remembered for being a lot more action-packed than previous installments. The signings of the top three free agents (Gerrit Cole, Stephen Strasburg and Anthony Rendon) were almost a watershed moment, since we had to wait until Spring Training had started last year for the top two free agents to finally sign their massive contracts.

At last year’s Winter Meetings, the Chicago White Sox made a blip-on-the-radar trade, acquiring starting pitcher Ivan Nova from the Pittsburgh Pirates for minor leaguer Yordi Rosario and $500,000 in International Bonus money. Not exactly setting the world on fire but bigger things were expected with the pursuit of Manny Machado. In the Rule 5 Draft, the White Sox selected pitcher Jordan Romano from the Toronto Blue Jays and immediately sold him to the Texas Rangers for cash considerations.

This year’s winter meetings were not much more exciting than last, and there’s no huge signing to look forward to that explains the lack of movement. The only White Sox transactions to take place were the acquisition of outfielder Nomar Mazara from the Texas Rangers for Steele Walker, the 46th overall selection in the 2018 MLB Draft and considered the sixth-best prospect in the White Sox organization.

In the Rule 5 Draft, the White Sox made no moves until the minor league portion, when they selected pitcher Will Carter from the Yankees.

A lot of negativity came from the Mazara acquisition, and I can certainly see the reasoning, considering the fact that the front office made the point that they were going to really shake things up this offseason. A below-average corner outfielder isn’t exactly making anyone buy season tickets, so where do they go from here?

People are down on the team (as usual) but this time, it’s not so much the White Sox fault directly as it is the White Sox fault that they’re just not a “destination team.” It’s a fact that the White Sox offered more money to pitchers Zack Wheeler and Jordan Lyles, but both accepted less to sign with the Phillies and Rangers, respectively.

Both were interesting case studies in the White Sox not being a “destination.” Wheeler took less money because his wife wanted him closer to her New Jersey home, which made the White Sox look even more ridiculous since last off-season they figured the way to get Manny Machado was to tug at his heartstrings by bringing in his good buddy Jon Jay and his brother in law, Yonder Alonso. This year, family did matter.

Jordan Lyles, while not a huge acquisition, struck me as even more strange. He turned down less money to sign with the Rangers without giving a reason, but acknowledged the fact that his best season to date (12 wins in 28 starts with a 4.15 ERA and a 1.7 WAR) was a result of working with catcher Yasmani Grandal, now with the White Sox. But apparently working with the catcher that helped him succeed and making more money than he would have made with the White Sox was not enough to seal the deal.

I truly believe the White Sox were going into the Winter Meetings expecting to “win the offseason,” and they had the rug yanked right out from under them.

Rick Hahn and Kenny Williams love to fall back on the rebuild and use that as an excuse every time something doesn’t go their way. After the Machado deal went nowhere last year, the company line was “we were a year too early,” which I agree, made sense. However, what did I hear from Hahn after the Wheeler deal failed? “we are probably a year too early.” Yeah, that’s the kind of excuse that works exactly once.

Unlike every other team in baseball, the White Sox front office does not want to be competitive one second before they absolutely have to be. I’m not sure where this mindset came from, or if it’s just loser thought from a loser franchise, but they are already falling back on the “it’s just year four of the rebuild,” which I expected, but they are spicing it up a bit with “the rebuild slowed down in 2019 due to injuries in the minor leagues,” which means they can try to add a year or two at the end and make it a six or seven-year rebuild instead of five, simply to cover their butts for more losing seasons.

Meanwhile, the Yankees have signed Gerrit Cole to a nine-year contract and I doubt they are going to just lay down and let the White Sox walk all over them when it comes time for the Sox to finally be “competitive.” It may just get uglier.

I still see parts of this rebuild that remind me of the 20-year rebuild of the Pittsburgh Pirates, which began in 1993 and finally ended with a playoff appearance in 2013, the first of three Wild Card appearances. But, alas, it went nowhere, no World Series appearances, let alone a championship. Is that in the White Sox future? Maybe.

So, as we move from the 2019 Winter Meetings into the holiday season, little is expected to change until January rolls around. At that point, expect the remaining free agent pitchers (Ryu, Keuchel and Bumgarner) to finally find new homes and I don’t see the White Sox making a major push for any of the above. I see more of a plan of re-signing Ivan Nova and bringing in a pitcher like Shelby Miller on a minor league deal, like the White Sox did last offseason with Ervin Santana, which was a major disappointment.

The White Sox are not close to contending, regardless of what fan boys and manager Rick Renteria will tell you. The pitching staff has one verifiable starter in Lucas Giolito, followed by question marks with Michael Kopech and Carlos Rodon (injury), Dylan Cease and Reynaldo Lopez (poor production) and a few minor league options.

And the push for 2021 being the “White Sox year” when it comes to free agency, it seems the train has already left the station because 2021 is going to be one of the weakest free agent classes, especially for pitching, in the past decade or more.

Red Sox outfielder Mookie Betts will absolutely be the gem of the players available, while a few will command big money deals and get them (including Astros outfielder George Springer, A’s shortstop Marcus Semien and Phillies catcher J.T. Realmuto potentially hitting the open market, depending on if any sign extensions before then).

The pitching that will be available is nothing to get excited over, the best likely being Robbie Ray of the Diamondbacks (an All Star in 2017) and Marcus Stroman of the Mets (a 2019 All Star despite finishing the season with a 10-13 record). Neither is the kind of pitcher you want as your #1 or #2 option on a championship team.

There is a part of me that truly believes the White Sox hope is that they can fill in their entire team with players they have drafted, minor leaguers they have acquired via trade and castoffs or “change of scenery” players and avoid having to pay a true “superstar” to play for the team. This will get to be a problem as guys like Yoan Moncada and Giolito head into salary arbitration and, eventually, free agency, unless they can pull the Chris Sale/Jose Quintana/Eloy Jimenez trick again and sign them to friendlier deals.

I’m not saying it’s impossible, but look at the Astros, whose rebuild is the blueprint other teams like to follow, and even though they have a fantastic minor league system with a number of home-grown talents on their MLB roster, they still had to supplement that group with Cole, Justin Verlander, Zack Greinke and Michael Brantley in order to reach the World Series. You have to acquire top talent to be a top team in this era.

So, a lackluster Winter Meetings performance (which is less the Sox fault than it was last year) will leave the team as a third place entity behind the Twins and Indians in 2020 and if Kopech and Cease and Lopez develop into front-line starters, a run at a Wild Card birth is possible but I’m thinking this team is going to finish 2020 at 82-80.

I’ll blog again in the event there is some kind of free agent signing or trade acquisition between now and the start of Spring Training. Thank you for reading.

And GO SOX!