MLB Mock Trade: Chicago White Sox Deal Luis Robert, Andrew Benintendi To Giants

Breaking news: The Chicago White Sox stink.

Chicago dogs are elite. It's still there. The White Sox suck at baseball pic.twitter.com/29avXsf9mC
— Definitely Nick (@other_st_nick) May 24, 2025

To their credit, they don’t smell quite as badly as they did in 2024, when they broke the MLB record for losses in a season (121). Here in ’25, they roll into the second half of the campaign standing at 32-65, which gives them a winning percentage of .330. That’s garbage, for sure, but it’s better than last season’s .253.

Hey, a silver lining is a silver lining.

The Pale Hose have the second-worst record in the league, 9.5 games ahead of the dreadful Colorado Rockies, who show no signs of making a run. Thus, barring an epic losing streak, the Sox will not finish at the bottom of the bottom.

Again, silver linings.

Okay In the Bay?

Meanwhile in San Francisco, the Giants are just half a game out of a Wild Card berth, and some batter’s box juice might get them over the edge

San Fran’s leading full-time position player, Heliot Ramos, is hitting .262 with an OPS of .766, all of which merits a gigantic “blah.” Their 399 runs scored ranks as the tenth-worst in the league, and had their pitching staff not compiled an impressive 3.50 ERA, they’d be fighting with Arizona for fourth place in the NL West, with nary a Wild Card dream to be had.

So here we have a perfect MLB trading storm: One pseudo-contender that needs runs, and one awful team that needs a future. Maybe they could pull off a deal like this:

San Francisco Giants receive:

LF Andrew Benintendi

CF Luis Robert Jr.

Chicago White Sox receive:

1B Bryce Eldridge (Giants’ #1 prospect)

LHP Carson Whisenhunt (Giants’ #3 pitching prospect)

OF James Tibbs III (Giants’ #3 prospect)

Everybody’s (Probably) Happy

The Sox, in addition to landing a trio of studs-in-waiting who will bolster their emerging farm system—a system that MLB.com ranks as the league’s sixth-best—jettison a pair of contracts they’ve been trying to shed for what seems like decades.

As for the Giants, sure, Robert and Benintendi have their fair share of shortcomings: After a fantastic start to his career, Robert have been mired in an 18-month slump, while Benintendi hasn’t finished a season with a batting average above .300 since 2022.

But their respective downslides could be blamed on Chicago’s general lousiness. There’s a possibility that a change of scenery—not to mention the opportunity to join a roster and a team culture that’s actually, y’know, good—could help them find the form that landed them their inflated contracts.

Remember, Robert is only 27, and if his new digs do indeed bring the former All-Star back to life, the Jints have themselves a key contributor for the next half-decade. And in the scary National League West, they’ll need all the contributors they can get.

Okay In the Bay?

San Francisco Giants receive:

Chicago White Sox receive:

Everybody’s (Probably) Happy

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