No. 1 Trade, Luis Robert Jr / Eloy Jiménez
If the Pittsburgh Pirates want to create a championship-type outfield core, they should consider trading for either Luis Robert Jr. or Eloy Jiménez, if not both, because they could be one of the best one-two punches while having years left before free agency.
Robert has around 4 years left on his six-year, $50 million contract, with two of the years being club options for $20 million a season. He will be earning $15 million in 2025 and $12.5 million in 2024, with Jiménez likely having to move to DH or occasionally playing outfield like Giancarlo Stanton. Jiménez, like Robert, signed a long-term contract, which will see him getting paid $13 million in 2024, with a club option in 2025 and 2026 worth $16.5 million and $18.5 million.
Robert finally had his breakout season in 2023, and Eloy has been due for his breakout season, but due to injuries, he has been unable to. If the Pirates acquire him and he finally breaks out, this trade could make a Pirates' dynasty, but if it goes wrong, it could also fracture the future.
The White Sox will likely want something like a king's ransom for both of them combined, so this trade would likely have to be headlined from the Pirate side with either Henry Davis or Endy Rodriguez.
The Pirates seem unlikely to trade Rodriguez due to his age and future projections, which could mark him as one of the best catchers in the league in future seasons, while Davis has dealt with a few injuries and is older. So, his current abilities being lower than Rodriguez at a younger age are quite concerning after getting drafted first overall in 2021.
Using MLB trade values, I calculated what a possible trade would look like to fill some holes in the White Sox roster, as well as adding depth that could develop, but the cost of trading for those two could likely be higher.
In a perfect world, I would project that to acquire both Robert and Jiménez, it would likely cost Henry Davis as the key piece, as well as young developing MLB ready talent like Liover Peguero, Ji-Hwan Bae, and Bailey Falter. A pitching prospect such as Thomas Harrington would likely be required as well.