White Sox trade talk: 9 guys who could be dealt in a win-now move

Chicago White Sox fans only saw what it takes to make a splashy trade last summer.

You will likely see it for years to come as well.

It took Nick Madrigal and Codi Heuer to pry Craig Kimbrel away from the Chicago Cubs in this big deadline deal, one which, while it didn’t work at the time, seemed worth the steep price tag. Months earlier, Dane Dunning went the other way on the deal that landed Lance Lynn. For a World Series contender bringing in the pieces it takes to chase a championship, promising youngsters are the typical toll.

RELATED: Why the Sox’s return to the potential Kimbrel trade is hard to predict

White Sox fans might be tearing their hair out that the failed Kimbrel acquisition means the team is in dire need of a second baseman this winter. But that should be high on Rick Hahn’s to-do list once lockdown is over and baseball’s offseason — no matter how close before spring training begins — can resume.

As previously explored, what appears to be the best way for the White Sox to plug this hole with an Impact player would be through trade. And while second base tops the list, Hahn could explore many other trading scenarios to make waves elsewhere on the list as well. There is an opportunity to add a big bat playing on the right field. And despite a full five-man rotation, many fans are hoping for another dominant arm in the starting XI.

If the White Sox do any of this, they’ll be forced into another situation where they’ll have to part ways with some young talent in order to move up for a run at the World Series.

Who can you part with at the moment? Let’s take a look.

Craig Kimbrell

He’s not young, but he has the unusual distinction of being openly discussed as a trade candidate by his general manager, making a deal seem likely. There’s certainly a possibility that Kimbrel could make a difference for the White Sox. Even after his sour few months with the White Sox, he seems to appeal to many teams, especially those looking for a closer team. His pre-trade numbers with the Cubs — a .49 ERA in 39 appearances — were good enough that Hahn should have no trouble finding a prospect. That’s how much he can get back after the somewhat spectacular mistakes Kimbrel endured in front of Liam Hendriks in 2021.

Andrew Vaughn

It seems highly unlikely that the White Sox would trade in Vaughn. He’s had a successful rookie season, he’s consistently garnered rave reviews from team bosses, his surprising versatility affords the White Sox a great deal of luxury, and he’s a big part of their plans for 2022 and beyond. But we said a lot about Madrigal. Hahn’s deadline splash reinforced his repeated insistence on never taking anything off the table and parted ways with a player who, despite an injury, ended the season as his second baseman and looked that way for a long, long time. Vaughn, of course, comes with a likely higher offensive cap. But that’s the kind of thing that can land an All Star in a trade. No one is suggesting Vaughn is going anywhere, but Madrigal is a cub now, something we would have thought impossible this time last year.

Gavin Leaves

Sheets and Vaughn were rookies last season and got their first taste of the big leagues. So don’t expect the numbers they set out in 2021 to be repeated in 2022 and beyond. But while they all had their struggles, they combined into one fierce, fearsome hitter. Vaughn dominated left-handed pitching with a .938 OPS against them while Sheets smashed right-handed with a .900 OPS. Keeping them both on draft at DH or in the right or wherever for 2022 wouldn’t be a bad thing for the White Sox. But Sheets could also be among the players spurring interest in trade talks that left-handers are a valuable thing – he’s had four hits in three playoff games. The obvious downside to separating Sheets? He could develop into the kind of impact guy the White Sox are looking for, especially as time goes by and more opportunities open up at first base or in right field or at DH. But remember, it’s time to win on the South Side right now.

Crochet Garrett

The White Sox are still figuring out how they’ll use Crochet, the 2020 first-rounder who’s promoted to the major leagues, in 2022. Given the exodus from the major league bullpen, they may be best off keeping him there rather than adding to the Auxiliary Corps overhaul. But they see him as a long-term starter, not that there’s room for him right now. Crochet could very well join Lucas Giolito, Dylan Cease and Michael Kopech as a near-future rotation once veterans like Dallas Keuchel and Lynn eventually move on. But he also has enough advantages that he could take a big chunk from another team looking to install a lanky left-hander — remember those draft-night Chris sale comps? – in its own rotation of the future.

Jared Kelly

The minor leagues are no longer the must-have for White Sox fans in the Reconstruction years. But while there’s a lack of high-profile names like Kopech, Eloy Jiménez and Luis Robert, the closet isn’t exactly empty. Kelley is one of the more enticing names for teams who might be asked what it takes to compete in an impressive big league. Maybe not enough to build a package on my own, but people got excited when the White Sox landed Kelley, an exciting high school pitcher, in the second round of the 2020 draft. That thrill could also extend to potential trading partners.

Jake Burger

Burger has been through a lot and endeared himself to White Sox fans in the process. At the big league level, there doesn’t appear to be many options for the former first-rounder, anchored with Yoán Moncada in third place. Burger played at second base in the Minors last season, but even after Madrigal went under, the White Sox didn’t seem keen on throwing Burger as an everyday starter in the middle of a playoff chase and eventual stopgap César Hernández to exchange But he’s still No. 3 in the organization, helped by a great return-to-action year at Triple-A Charlotte. Burger could definitely get a chance as a reserve at the big league level, but maybe the best way to solve the second base problem isn’t to bring Burger there, but use him to get someone else?

Colson Montgomery

The White Sox are in win-now mode and while Hahn has remained committed to ensuring long-term success, the window of contention is now open. So someone with an estimated major league arrival date of 2025 could be relatively expendable with the White Sox chasing a championship in the present. Montgomery was the team’s first-round pick in last summer’s draft, a high school shortstop who has rocketed to the top of the organization’s prospect rankings. He’s left-handed, only 19 years old, and gets compared to Corey Seager – not to mention Tony La Russa likes what he sees. Sounds like he’ll be looking good in a White Sox uniform in half a decade. But that same appeal could allow Hahn to land the plays he needs for modern-day title chases. No one should envy making that kind of decision — trading teenage shortstops hasn’t gone the way of the White Sox lately — but such is life in the middle of a contentious window.

wes cath

Just as Burger and Sheets were drafted in the first and second rounds as fixed points for the dream infield of the future, the White Sox may be pursuing a similar strategy with Montgomery and Kath, the latter a shortstop turned third baseman picked from the top became school in the second round of last summer’s draft. Kath is already No. 4 in the organization, three spots behind Montgomery, and although the boys named Moncada and Tim Anderson, hardly over-the-top vets, will likely have something to say about how long a climb to the majors will last for Montgomery and Kath, there’s a lot of promise there – enough that the factors that apply to Montgomery might also apply to Kath in Hahn’s trade talks.

Yoelqui Cespedes

It doesn’t seem likely that the White Sox would spend a few million dollars to win the 2021 top player in the international signing league just to trade him. We’ll see if Céspedes can offer a legal field upgrade from within the organization later this year. Until then, however, perhaps only the “take nothing off the table” approach might offer a path to making it the trade piece that earns a significant piece in the major leagues.

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