Potential answer at second base?
Like Kepler, Polanco is closing in on the end of a contract extension he signed ahead of the 2019 season. However, Polanco would come with two years of control due to his contract including a club option for the 2025 season. Due to this, Polanco would likely cost more than Kepler via trade, but he would be a perfect with the Pirates.
Polanco is coming off a season in which he hit for a .255/.335/.454 slash line, with a 118 wRC+, 118 OPS+, 10.5% walk rate, 25.7% strikeout rate, and an ISO of .199. This would be a massive upgrade over what the Pirates got from the second base position in 2023.
Last season, Pirate second basemen hit for a .228/.296/.335 slash line with a 71 wRC+, .107 ISO, and a 26.8% strikeout rate. Pirate second basemen were 25th in the majors in ISO, 26th in on-base percentage, and 28th in slugging percentage. Their -1.1 fWAR ranked 29th. Flat out putrid numbers.
Not only would Polanco be a huge upgrade for the Pirates, being under team control through 2025 makes him the perfect bridge for second base until Termarr Johnson is ready for the majors. Arguably the best second base prospect in baseball, Johnson should be on track to reach the majors at some point in 2025. This would allow Polanco to give the Pirates great production from second base for two seasons, before handing the reigns over to Johnson full-time following the 2025 season.
Now, will the Pirates pursue either of these players? Probably not. Nothing Cherington has done indicates he is willing to part with the pieces necessary to swing a trade of this caliber. So this is probably a wasted exercise to even discuss it.
However, landing one of Kepler or Polanco, let alone both, would vastly improve the team's chances of contending in 2024. Attempting to contend in 2024 should be the goal for Cherington and the Pirates. But is it the goal? Well, that is certainly debatable.