Following the conclusion of the 2021 World Series, the first few transactions have begun to hit the wire and the offseason has officially begun. Instead of reading too deep into Rick Hahn’s recent media hits or lamenting about the inevitable disappointment from the Chairman’s checkbook, I am getting ready for the offseason by taking inventory of the White Sox trade assets and how they match up with the conceivable trade opportunities across the league.
Typically, the first dive into the offseason entails going to MLB Trade Rumors for the free agent list and starting to wish on the best players who are without a contract for 2022 and beyond. Despite a strong free agent class, I don’t see that all that many players on the market that fit the current holes and weaknesses of the White Sox roster. Of course, there are plenty relievers that make sense and the Sox will be in the market but I will put them aside for ease of this conversation. That said, I do think that there a few targets in free agency - specifically two - that need to be addressed before delving into the trade possibilities that I think will ultimately shape the White Sox’ offseason.
MICHAEL CONFORTO
First and foremost, Michael Conforto. Seems like everybody has caught onto this one because the fit is so natural. Since the Sox have started using the offseason as a way to build a winning team, I have called out a free agent each year that I found to be perfect for the Sox in 2019 and 2020 in Yasmani Grandal and Liam Hendriks. This year, that free agent is Michael Conforto. The White Sox need to get more left-handed, they need more OBP and they need to get better defensively. Conforto certainly helps with the left-handed bat and has a lifetime .356 OBP with the Mets over seven seasons. Defensively, Conforto, at the very least, will be an improvement over the career-long-infielders the Sox threw out there in 2020. Conforto would slide perfectly into the middle of the White Sox right-handed heavy lineup.
Conforto’s market should be interesting as left-handed power bats are always in demand and the prognosticators seem to be all over the place with the projections of a potential deal. Some expecting the 28-year-old to take a 1-year prove it deal and others projecting a nine-digit-type contract. I think the deal will end up somewhere in the middle. Nick Castellanos’ 2019 deal with the Reds is a good model for the lefty-bat in my view. Adjusting for inflation, something like a 4-year, 70 million dollar pact with an opt-out following the second year of the deal makes sense for me. Putting all the complications of the pending collective bargaining agreement, I think the Sox would try to jump the market on Conforto and sign him early into the offseason a la Yasmani Grandal in 2019.
MAX SCHERZER
The second free agent of note will cause some to roll eyes and other to grown about Reinsdorf and I get it but...that free agent is Max Scherzer. There is no player on the market that would improve the White Sox World Series’ odds like Max Scherzer. I know people will say the Sox would never spend the money necessary and I know that view is always in vogue but I don’t really care. For the past few offseasons and this recent trade deadline, there have been very few voices saying the Sox will spend and they have. I fully expect the team to open 2022 comfortably in the upper third of MLB payrolls and I am open for bets if anyone disagrees.
The problem with Scherzer is that money is only part of the picture. If the guy liked LA and LA is intent on him heading up their rotation, the Sox don’t have much more than a puncher’s chance. In terms of spotlight and an opportunity to win, the Dodgers are as good a place to be as anywhere. We will see what Scherzer wants though. The White Sox are in a world class city that opposing players love to visit and they will open 2022 with the best odds to win their division in, at the very least, the American League, if not all of baseball. If a player prioritizes an opportunity to win the White Sox are a top destination. We’ll see if he even explores the market though.
I would put the chances of the Sox converting on this far below their chances with Conforto but this is the move they have to put all their marbles into if Scherzer gives them an opening. Reinsdorf and his buddy managing the team are well into their twilight years and a potential Scherzer acquisition would move the needle unlike any other. If Scherzer is willing to leave the coast and wants flexibility (opt-outs, buy-outs, incentives, etc.), I like having Hahn’s deal-crafting on our side. As a pitcher who competes on the mound with a psychotic’s vigor, I like having Kenny Williams adjacent to the new school exec Rick Hahn at the negotiating table.
Despite what fans may think, Kenny Williams is an executive players can gravitate to. In an era of baseball with front offices littered with Ivy League types, the Sox are fortunate to have a former player with an attitude like Kenny Williams at the helm. Just ask Max Scherzer’s former teammate Bryce Harper - who was impressed and intrigued by the White Sox’ Williams in the team’s 2018-2019 pursuit of Harper that came up short in dollars.
A Scherzer deal would likely be a short term deal with an AAV north of $30M as the future Hall-of-Famer will turn 38 in 2022. With Reinsdorf’s blessing towards the money, I’ve little doubt this is the player Rick Hahn and Kenny Williams are dreaming about going into this offseason. Skeptics are warranted here, but this is the right move at the right time. It may be a longshot, but I am of the view it’s “unlikely” as opposed to most views of this being outside the realm of possibility.
Past those two free agents, the White Sox will scour the relief market. Depending on the other moves, they can be in the top of the relief market, the middle, the bottom or multiple levels but they will not neglect the pen. While they need to address 2B, there aren’t may options out there of the starter caliber. I wouldn’t be shocked if they brought back Hernandez on a cheap deal. All that said, my point of writing was to speak about the possible trades. I just wanted to address the free agent approach before diving into the trade possibilities in long form.
LOOKING AHEAD
I don’t know how much I will write. I don’t know how much this will be viewed. I do want to know what readers think and what readers would want me to write about in the future if anything. So please, email me, tweet me, etc. and let me know what you think, what you want, etc. My next pieces will be on the trade possibilities - both internal and external.
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