The World Series is over. Let the offseason games begin.
This figures to be a mighty important winter for the White Sox, who could start the transition from rebuilding mode to contending mode with some impactful moves over the next few months. Rick Hahn’s front office has some specific items on the to-do list, including finding a new right fielder, a new designated hitter and some starting-pitching help. Don’t be surprised if the bullpen gets some new faces, too.
So when’s all that going to happen? The last two offseasons have been like watching paint dry, at times, with free-agent signings few and far between — and some of the biggest names in the game waiting until spring training to ink deals. It would be no shock if that happens again, but of course we’ll have to wait and see.
But there are some concrete dates on baseball’s offseason calendar, and we can look at those and some of the White Sox pending decisions and see where some things might line up.
The next five days: decisions on free agents, options and opt outs
Players can officially file for free agency Thursday, the day after the end of the World Series. But free agency itself won’t start until next week. Over the next five days, teams can negotiate (but not sign) their own free agents. For the White Sox, that means Jose Abreu, among others.
Considering Abreu spent the 2019 season endlessly describing his love for the White Sox organization, his excitement about being a part of the team’s bright future, chairman Jerry Reinsdorf’s supposed promise that he’ll never wear another uniform and his plans to sign himself to a contract should the White Sox not extend one, Abreu’s return to the South Side for the 2020 campaign and beyond has long seemed a foregone conclusion.
But the White Sox actually do have to sign him to a new contract, and while that can’t happen until Tuesday, they can negotiate with Abreu’s representatives — something they did not do during the season — over the next five days. Given the love between the two parties, it wouldn’t be surprised to learn of a new deal for Abreu first thing out of the gate come the start of free agency. But Hahn has brought up how things went down with a similarly beloved franchise icon in Paul Konerko many years ago, when that All-Star first baseman went to free agency and didn’t re-sign with the White Sox until deep into the winter.
Of course, the White Sox also have the option to extend a qualifying offer to Abreu, which if accepted would keep him employed for one more season and send him to free agency next winter. If declined, he would go to free agency and could sign with any team. If that team was anyone besides the White Sox, they would receive draft-pick compensation for losing Abreu. If a qualifying offer were to be extended to Abreu, it would come at the end of the next five days. If the White Sox end up extending a qualifying offer to Abreu, the deadline for him to accept or decline that is 15 days after the end of the World Series (Nov. 14).
But that all seems unlikely, and Abreu returning to the White Sox on a new multi-year deal still seems the most likely outcome.
Other, non-Abreu business the White Sox will need to take care of in the next five days: 1. deciding whether to pick up or decline the team option on Welington Castillo and 2. deciding whether or not to negotiate new contracts with other pending free agents Ivan Nova, Ross Detwiler, Jon Jay, Hector Santiago and Brandon Guyer.
It would be rather surprising to see Castillo back with the White Sox next season considering how disappointing the last two seasons were for the veteran catcher. He served that 80-game suspension after testing positive for a banned substance in 2018, and he hit just .209 with a .267 on-base percentage in just 72 games in 2019. The emergence of James McCann makes Castillo seem all the more expendable.
While Nova is actually an intriguing option to provide some rotation depth after a strong second half this season, it would be similarly surprising to see any of those non-Abreu free agents handed new contracts at the immediate start of what’s expected to be a lengthy free-agent process.
Also in the next few days, we will know about the availability of some of the biggest names that could hit the free-agent market, specifically J.D. Martinez and Stephen Strasburg, who can both opt out of their contracts with their current clubs. Strasburg, pitching with the Washington Nationals in the World Series, faces the earlier deadline, needing to figure out whether he’s going to free agency or not three days after the Fall Classic ends. Martinez has a little longer, five days after the World Series ends Wednesday night.
Martinez seems like a perfect fit for the White Sox, the prime free-agent candidate to plug their hole at DH. While no interest on their part has been reported to this point, logic says they’ll want to know whether Martinez hits the market or stays with the Boston Red Sox. We’ll all know within the next few days.
Nov. 11 through Nov. 14: GM meetings
While there was little to no actual activity at last year’s GM meetings, they did provide one of the biggest moments of the White Sox offseason: the rumor describing their intention to pursue the two biggest names on the free-agent market, Manny Machado and Bryce Harper. They ended up doing just that, and what seemed like little more than a dream in October was ushered into reality in November.
Of course, the White Sox didn’t land either player, something that a year later still has many fans agitated, but they did chase them all the way into spring training, showing an aggressiveness that matched Hahn’s plans to bring in a top-of-the-line player from outside the organization to complement the homegrown core.
That aggressiveness figures to be back this winter, and there is no shortage of free-agent targets the White Sox could pursue to accomplish those goals. Any rumors linking them to those big names will come as less of a surprise this time around, but they could still pop up at the GM meetings or elsewhere during the month and help dictate how we talk about the White Sox for the remainder of the offseason.
Nov. 3 through Nov. 18: Awards season
Baseball’s biggest awards will be handed out in the first few weeks of November. The White Sox might have finished with 89 losses, but they had many breakout individual performances that might have earned placement in the balloting.
Nov. 3: Gold Gloves. Yolmer Sanchez and Lucas Giolito are finalists at their respective positions, with Sanchez potentially the favorite at second base.
Nov. 4: finalists announced for MVP, Cy Young, Rookie of the Year and Manager of the Year awards
Nov. 7: Silver Sluggers. Abreu had one of the more productive seasons of his six-year big league career after starting the All-Star Game at first base. Tim Anderson was the AL batting champion. Yoan Moncada was the team’s best all-around hitter. Will any or all of them win Silver Sluggers?
Nov. 11: Rookies of the Year. Eloy Jimenez hit 31 homers in his rookie season. It might not be enough to top Houston Astros slugger Yordan Alvarez in this race, but he should be a finalist and top-three finisher.
Nov. 13: Cy Young Awards. Giolito has a chance to be named one of the three finalists for the AL Cy Young Award, but even if he isn’t, we’ll figure out how high he placed in the voting.
Nov. 14: MVPs. Could Abreu, Anderson and Moncada finish somewhere in the balloting?
Nov. 18: Comeback Players of the Year. Giolito could earn some consideration here, too, and potentially win the award after a transformational season.
Dec. 2: non-tender deadline
The White Sox have eight arbitration-eligible players, and they have until Dec. 2 to decide whether to tender them contracts for the 2020 season or not. As discussed here plenty, Sanchez seems to be the biggest question mark of the bunch, due a sizable raise that could price him off the White Sox roster. Considering the nearing arrival of Nick Madrigal, the light-hitting Sanchez — who the White Sox love for his defensive excellence and off-the-field contributions in the clubhouse — seems likely to be relegated to reserve status at some point during the 2020 season. Is that worth a projected $6.2 million?
Alex Colome is projected to receive $10.3 million through the arbitration process, but though that sounds steep, he’s been one of the more dependable late-inning pitchers in recent seasons. The White Sox twice made the decision to keep him in their plans, first by trading for him last winter and again by not trading him at the deadline, so they seem dedicated to having Colome as their closer next season.
As for the others, McCann, Leury Garcia, Carlos Rodon and Evan Marshall figure to be tendered contracts. Ryan Goins was arbitration eligible but was outrighted this week and will head to minor league free agency. Josh Osich is an interesting case considering he performed admirably and often for Rick Renteria last season, but his 2019 numbers won’t blow anyone away. He also has the best entrance music on the team, Fleetwood Mac’s “The Chain,” but that likely won’t factor into the White Sox decision.
Dec. 9 through Dec. 12: Winter Meetings
While free agency starts six days after the World Series ends, with players eligible to sign throughout the month of November, the glacial pace of the offseason in recent years has changed our expectations to minimal activity until the Winter Meetings roll around. Traditionally, it’s when the hot stove really gets cooking.
Last year, the White Sox traded for Nova during the Winter Meetings, and within hours/days of leaving Las Vegas (Sheryl Crow style), they had signed McCann and traded for Yonder Alonso. Fans are obviously hoping for bigger, more impactful moves this time around, and the White Sox are, too.
But if the Winter Meetings — in San Diego this year — come and go without items being entered into the transaction log, don’t fret. Teams spent last year’s Winter Meetings sitting down with Harper and Scott Boras, the agent who represents nearly all of the biggest names on this winter’s market, too. That included, reportedly, the White Sox, who were in pursuit until the spring. The point being that stuff that goes on during the Winter Meetings can lead to stuff happening months later.
Given the White Sox planned aggressiveness and their list of needs, it wouldn’t be surprising to see them try to get some important moves made during this year’s Meetings. But it’s difficult to predict that things will end up going that way. We’ll have to see how the market plays out.
Dec. 12: Rule 5 draft
The Rule 5 draft takes place during the Winter Meetings, and the White Sox will spend the next month and a half reorganizing their 40-man roster as to protect notable prospects now eligible for selection. That group includes Dane Dunning, Blake Rutherford, Jimmy Lambert, Bernardo Flores, Zack Burdi and Yermin Mercedes, and if the White Sox don’t want to lose any of those players in the Rule 5 draft, they’ll have to remove other players from the 40-man roster.
That process is well underway, with Charlie Tilson’s departure preceding the outrighting of Manny Banuelos, Ryan Cordell, Goins and Matt Skole this week. Those decisions seemed relatively easy, same with the pending ones involving the aforementioned free agents to-be Castillo, Nova, Detwiler, Jay and Santiago. But those spots could fill up again quickly, with injured pitchers Rodon and Michael Kopech needing to move back to the 40-man. Any additions made before or during the Winter Meetings would take up space, too.
Jan. 24 and 25: SoxFest
The team and fans are hoping to have some big additions to celebrate at SoxFest in January. You’ll remember that Hahn was greeted with chants of “MAN-NY! MAN-NY!” at last year’s event, so it’s quite possible the biggest free-agent business will remain unsettled come Jan. 24 and 25. But in an ideal world, you’ll be able to line up for an autograph from Martinez or Gerrit Cole or Madison Bumgarner or someone of that ilk alongside Giolito, Anderson, Moncada and Jimenez.
Remember, too, that SoxFest has a new location and a new setup this year: It’s a two-day event at McCormick Place. Plan accordingly.
February: arbitration hearings and spring training
January and February bring other arbitration-related dates: Players and teams exchange arbitration figures on Jan. 10, and arbitration hearings take place over a three-week span in February. So if the White Sox go to arbitration with any of their arbitration-eligible guys — as opposed to those players agreeing to contracts with the team — that’s when all that will take place.
If things play out the way they have in each of the last two offseasons, the White Sox and baseball’s 29 other teams could show up to spring training in mid February with some of the biggest names on the free-agent market still looking for work. If that’s the case, the offseason won’t truly be finished, and we could still be talking about the derbies for top free agents even as Renteria is writing out his lineups for the first Cactus League games.
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