SF Giants rumors: Five potential trades with the Chicago White Sox

With the SF Giants expected to be buyers at the MLB trade deadline, we looked at some potential trades with the Chicago White Sox.

After a slow start to the season, the SF Giants have surged into postseason contention over the past month. On the heels of a 10-game winning streak, the Giants are currently the second Wild Card in the National League and are in second place in the National League West. As president of baseball operations Farhan Zaidi looks to make the team's first deep postseason run of his tenure, he's expected to be aggressive on the trade market this summer.

The Chicago White Sox, who are currently in fourth place in the American League Central with a 32-44 record, seem likely to be sellers at the deadline. Here's a look at five potential deals that could appeal to both teams:

NOTE: White Sox starting pitcher Lucas Giolito is an obvious fit for the Giants as well, but I decided to leave him out of this piece because he's been tied to SF for a while now by trade speculation pieces. I assume most fans already have him in mind. He's a solid mid-rotation starter on an expiring contract. I could see the Giants building a package around someone like Grant McCray, Aeverson Arteaga, or Mason Black.

SF Giants catcher Joey Bart throws the ball to third base. (2023)

SF Giants-Chicago White Sox Trade Proposal #1
Yasmani Grandal for Joey Bart

The Giants seem content rolling with Blake Sabol as their backup catcher. However, if they are worried about their depth behind Patrick Bailey (who has had stints on the injured list in his previous pro seasons), they could look to turn Bart's controllable upside into a short-term insurance policy at catcher.

It's unclear exactly how much Grandal, who is 34, has left to offer at this point in his career. He's hit .262/.318/.391 so far this season, and most advanced numbers are even lower on his overall performance. His defensive metrics have also taken a massive hit compared to his once elite peak.

Nevertheless, if the Giants have given up on Bart, and are nervous about having to rely on Sabol's defense in a potential pennant race, it might not be the worst idea to give Bart the change of scenery it seems like he needs and solidify their depth at the position. For the White Sox, they turn a rental in Grandal into a lottery ticket on the former second-overall pick in the draft.

White Sox pitcher Liam Hendriks reacts after getting the final out. (2023) / Brad Penner-USA TODAY Sports

SF Giants-Chicago White Sox Trade Proposal #2
Liam Hendriks for Ross Stripling, Grant McCray, José Cruz, Hayden Birdsong

The Giants bullpen sure does not look like it needs reinforcements right now, but it can never hurt to add another high-octane option. Liam Hendriks was one of the best closers in MLB from 2019-2022, but missed the start of the season after undergoing cancer treatment and is currently on the injured list with an elbow injury. The injury does not have any structural damage, suggesting he could return to the field at some point this season.

Hendriks is making $14 million this season with a club option for $15 million in 2024. If the White Sox are sellers at the deadline, it would be worth listening to offers. The Giants, a team who has not shied away from acquiring relievers who are in the middle of even more serious injury rehabs, would seem like an obvious fit.

For one, the Giants could attempt to swap one of Ross Stripling or Sean Manaea's two-year, $25 million contracts for Hendriks, helping them solve their backlog of starters while also offsetting most of the money in Hendriks' contract. From there, it comes down to prospects.

McCray would be the centerpiece of this deal for the White Sox. The 22-year-old center fielder has had his ups and downs this year at High-A, hitting .229/.335/.397 with nine doubles, four triples, eight home runs, and 28 stolen bases (35 attempts) in 63 games. He is an elite defensive outfielder with plus-plus speed, plus power potential, and a penchant for walks but struggles with swing-and-miss.

Cruz is a right-handed reliever on the Giants 40-man roster who has posted a 2.17 ERA with 123 strikeouts and 34 walks in 78.2 innings pitched over the past two seasons. Birdsong was selected in the sixth round of last year's draft and was recently promoted to High-A after dominating at Single-A. He's flashed a mid-90s fastball and a plus breaking ball, which should give him a decent floor as a reliever if he's unable to stick in the rotation.

The White Sox may prefer to bet on Hendriks returning to form and helping them contend in 2024. However, the Giants have the farm system depth, and have shown the willingness to gamble on injury risk, to give the White Sox an opportunity to make a move if they so choose. If healthy, Hendriks would give the Giants an unparalleled 1-2 punch in the back of the bullpen alongside Camilo Doval. If he faulters, the Giants would only be out some money and prospect depth.

White Sox shortstop Tim Anderson high fives teammates in the dugout. (2023) / Rick Osentoski-USA TODAY Sports

SF Giants-Chicago White Sox Trade Proposal #3
Tim Anderson for Casey Schmitt, Hayden Birdsong

This trade would probably enrage both fanbases. However, if the Giants believe they can buy low on Anderson while the White Sox see Schmitt as a potential member of a future core, this deal could make sense for both sides.

Anderson is struggling mightily this season with a .249/.290/.292 triple-slash. With that said, many of his peripherals (K%, BB%, whiff rates, hard-hit%, and average exit velocity) are in line with his previous numbers. While Anderson is 31, there's reason to believe he is capable of returning to his All-Star form from 2019-2022, when he posted a .313/.347/.474 line.

At worst, Anderson could take on the weak side of a platoon with veteran shortstop Brandon Crawford. Even in his struggles this season, Anderson has a .797 OPS against southpaws, which continues a career-long trend of mashing against lefties (.329/.354/.511 career line).

Anderson's contract includes a $14 million club option ($1 million buyout) for next season, which could be a public relations nightmare for notoriously-cheap owner Jerry Reinsdorf if the team declines it. But that option should make him even more enticing to the Giants if they believe they can get him back to his peak form.

If the Giants are eyeing Anderson, they will probably try to build a package around shortstop prospect Aeverson Arteaga. Anderson is the face of the franchise on the South Side of Chicago, though. With an already disgruntled fanbase, it's hard to envision the White Sox parting with Anderson without receiving some semblance of an MLB-ready return.

Enter Schmitt, who hit .293/.365/.485 with 28 doubles and 21 home runs last season between three minor-league levels, finishing the year at Triple-A. After an excellent spring training, Schmitt was a backend top-100 prospect and got called up to the bigs in May. He got off to a scorching start. However, he has since found himself in a prolonged slump.

Schmitt has plus power potential, but defense has always been his calling card. Schmitt is already a Gold Glove-caliber third baseman and has shown viability at shortstop this season as well. The White Sox front office could get behind Schmitt as their shortstop of the future, confident his defensive versatility gives him a solid floor. The Giants would probably have to throw in a secondary prospect, like Birdsong, to get the deal done, but Schmitt would be the calling card.

As much as Schmitt has ingratiated himself with the Giants fanbase, it's no secret that his aggressive approach is not something the organization prioritizes. It's also true of Anderson, but he's proven he can be productive against big-league pitching throughout his career.

Moreover, second baseman Thairo Estrada and third baseman J.D. Davis have had All-Star caliber seasons and are under team control through at least 2024. Barring trading one of those pieces, Schmitt's only immediate path to an everyday job in San Francisco is at shortstop. If the SF Giants believe they can help Tim Anderson return to his form from 2019-2022 (when he averaged more than 5.0 fWAR per 140 games), parting with Schmitt becomes foreseeable.

SF Giants infielder Marco Luciano poses for a portrait during photo day. (2023) / Mark J. Rebilas-USA TODAY Sports

SF Giants-Chicago White Sox Trade Proposal #4
Dylan Cease for Marco Luciano, Carson Whisenhunt, Grant McCray, Tristan Beck, Onil Perez

It's no secret that Dylan Cease will be one of the most coveted players at this year's deadline. Not only has he been one of the best starting pitchers in MLB since 2021, but he is also under team control via arbitration through 2025. So, the Giants, along with every other contender, will try to pry Cease away from the White Sox.

The question facing the Giants is can they build a good enough package to get Cease without surrendering either of their top two prospects (Kyle Harrison and Luis Matos) or either of Patrick Bailey and Schmitt (although Schmitt seems the most tradeable given the reasons mentioned previously)? I think they can, although the White Sox are in a position to refuse to make such a move purely from an optics standpoint.

This deal hinges on the White Sox's evaluation of Luciano. A consensus top-50 prospect in the minor leagues, Luciano remains a tantalizing power-hitting prospect. Not set to turn 22 until September, Luciano has blasted nine home runs in 39 games in the pitcher-friendly Eastern League with a nearly 15% walk rate. However, he's also struck out nearly a third of the time, driving down his unexceptional but solid .196/.310/.434 triple-slash.

There are shades of young Kris Bryant in Luciano. There are also shades of a player like Patrick Wisdom. If the White Sox evaluators see the former, then he could be the centerpiece of a package for Cease; if they see more of the latter, though, they probably will not make a deal without at least one of Harrison, Matos, Bailey, or Schmitt.

Whisenhunt is on a fast-track trajectory to the majors. He is trending toward landing on top-100 prospect lists by the end of the year, having already reached Double-A in his first full pro season. A 22-year-old lefty with one of the best changeups in the minor leagues, Whisenhunt would be a safer complimentary piece to Luciano's combination of risk and upside.

By bringing in Cease, the Giants could allow the White Sox to pick a pitcher from their trio of up-and-down arms (Beck, Hjelle, and Keaton Winn). Beck has been the best of that group this season, recording a 3.05 ERA (3.37 xERA, 4.01 FIP, 4.00 xFIP) in 38.1 innings pitched (15 appearances) with the Giants. He might already be a viable MLB four-starter.

Finally, McCray and Onil Perez round out the package with two more upside prospects at positions of strength in the Giants farm system who are approaching Rule 5 Draft eligibility and are far away from the majors. Perez is an advanced 20-year-old catcher, hitting .313/.376/.413 at Single-A with nearly as many walks as strikeouts.

White Sox CF Luis Robert Jr. takes a swing at T-Mobile Park. (2023) / Stephen Brashear-USA TODAY Sports

SF Giants-Chicago White Sox Trade Proposal #5
Dylan Cease, Luis Robert for Kyle Harrison, Luis Matos, Marco Luciano, Onil Perez

There are many reasons a trade like this is not in the cards. For starters, is there any scenario where Zaidi would be willing to cash in his three top prospects? Moreover, selling teams rarely find it advantageous to trade multiple proven players in one deal. Front offices would usually rather shop each player individually to try and maximize the return.

Nevertheless, the Giants have a trio of top-50 (arguably top-30) prospects in the league. As high as the Giants may be on Harrison and Matos, it's hard to believe they would turn down the opportunity to trade Harrison for Cease or Matos for Robert straight up. If that's the case, it's easier to envision the Giants adding Luciano and secondary pieces to acquire a young, controllable frontline starter and middle-of-the-order center fielder.

Luis Robert is the second-best best defensive center fielder in the majors this season, per Outs Above Average, and is hitting .263/.322/.533 with 20 doubles and 18 home runs. He is still only 25 and is under contract through 2027. His aggressive approach and swing-and-miss tendencies are two things the Giants have veered away from under Zaidi, but Robert has been an above-average hitter in each of his four MLB seasons and is young enough to envision some continued development in his approach.

The Giants only make this move if they believe Robert and Cease are legitimate franchise cornerstones. They would try to sell the White Sox on Harrison and Matos as MLB-ready (cheaper) replacements for Cease and Robert at their respective positions, alongside the upside of Luciano and Perez. 

It would be a hefty price for the SF Giants to pay. This package would probably be the most prospect capital in one trade in recent history, with the exception of the Padres deal for Juan Soto last summer. However, a postseason rotation of Logan Webb, Dylan Cease, Alex Cobb, and Anthony DeSclafani alongside a potential starting outfield that features Michael Conforto in left, Robert in center, and Mike Yastrzemski in right is a tantalizing proposition.