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Questions White Sox need answers for entering Winter Meetings

Today, I make my annual pilgrimage to San Diego to visit my friend's holiday party. Well, technically speaking, it's supposed to be a work party that the expenditures are tax write off. Us Chicago folks are lucky enough to be invited, not like it requires a great deal of twisting our arms to spend a weekend out of the December cold.

This trip would be an excellent opportunity to get away from the sadness of the White Sox front office losing another free agent public bidding war. But, the baseball world is also coming to San Diego for this year's Winter Meetings. A four-day stretch where we used to see a flurry of transactions has been rather dull these past two years. You can make the argument the White Sox were the last team to make the Winter Meetings interesting back in 2016 when they traded Chris Sale and Adam Eaton away in back-to-back days. As MLB teams, MiLB teams, media, and job seekers make their way to the Hilton hotel; this offseason has been much more active early on.

The Winter Meetings begin on Monday, so I have packed up the podcasting equipment and decided to stay in San Diego a bit longer. Hoping to capture the news as it breaks from a hotel lobby and relay any gossip from the nearby bars. Rick Hahn should be a very busy man. He doesn't get an opportunity to think about what went wrong in his attempt to sign Zack Wheeler. The starting pitching market is moving at a quick pace with the Los Angeles Angels trading for Dylan Bundy, and Cole Hamels signing with the Atlanta Braves.

So what am I hoping to learn while in San Diego for the next week? Here are the questions I believe the White Sox need answers to ensure their offseason is a success in building a competitive team in 2020.

Will the White Sox pursue Hyun-Jin Ryu?

After losing out on Wheeler and Hamels, which direction will the White Sox take to improve the starting rotation?

The answer should be Gerrit Cole because Cole fits in any team's plan. Does Cole fit in every team's budget? Probably should, but let's not visit that dark place at the moment. Stephen Strasburg would also be a great addition. Either would give the franchise a much needed shot in the arm and could entice other players to give the White Sox more thought as a possible destination.

Unfortunately, it doesn't appear the White Sox are serious suitors for either Cole or Strasburg, which is a shame. After losing out on Wheeler, it's back to the drawing board for Hahn. One pitcher we have heard a few whispers about is Hyun-Jin Ryu. One would think there would be more rumors surrounding Ryu after finishing second in the National League Cy Young voting behind Jacob deGrom.

Age seems to be a significant factor as Ryu is 32 years old and will turn 33 a day before 2020 Opening Day. Despite the concern, it would be very advantageous for the White Sox to sign Ryu and pair him with his former battery mate, Yasmani Grandal. In 28 starts spanning 143 innings, Ryu had a 3.02 ERA having Grandal behind the plate striking out 139 and walking 45.

Plus, Ryu is not looking for a five-year deal like Wheeler. When he arrived home in South Korea in early November, Ryu told the media he is seeking a three to four-year contract.

https://twitter.com/stevestone/status/1202431291624345600?ref_src=twsrc%5Etfw

What are the White Sox going to do in right field?

Finding a starting pitcher appears to be the White Sox number one task at the moment, but they can't forget finding a solution to cover right field. Nicholas Castellanos and Marcell Ozuna have been long rumored as potential targets by the White Sox. There is more trade smoke surrounding Castellanos as the San Francisco Giants and Arizona Diamondbacks are interested in signing the 27-year old. The White Sox were so bad in right field that pretty much anyone they find should be an improvement. Still, they could use another impact bat like Castellanos or Ozuna.

What kind of trade will Rick Hahn make?

There is a lot of focus on free agents, but we can't discount Hahn addressing a team's needs through trade. The Joc Pederson rumors never seem to die because it makes a lot of sense for them to add a left-handed power bat to play right field. Another player rumored to be on the block is Starling Marte. Even with new GM Ben Cherington in place, it is still difficult to gauge on what Pittsburgh's plans are for this offseason. If Starling Marte is genuinely on the trade block, he could be an enticing option for the White Sox to address right field. His remaining contract is two years, $24 million, which is at a cheaper AAV than what it would take to sign Castellanos or Ozuna.

The offseason has been busy. Just this morning around 5:15 AM CT, The Athletic's Ken Rosenthal is reporting that old friend Omar Narvaez might be on his way to the Milwaukee Brewers. I hope this pace of transactions keeps up as it holds our attention as baseball fans through the winter. The White Sox are no strangers to grabbing headlines at the Winter Meetings. Hopefully, this time, it produces better results on the field.

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