At 43 years old, every season could be the last for Rich Hill. Hill is among the most well-traveled players in baseball history and that continued in 2023 when he started the season with the Pirates before getting traded to the Padres at the trade deadline last year. The deal didn't really work out as Hill struggled in San Diego with an 8.23 ERA in 10 appearances including five starts.
It remains unclear as to what the future holds for Hill. Frankly, it has been remarkable that he has been able to play as long as he has. The most current thinking is that Hill may not sign at all this offseason and instead will consider signing at midseason if he does at all. His career is clearly winding down and he has expressed a desire to spend more time with this family, so don't be shocked if he ends up deciding to just hang up his spikes and call it a career.
Of all the Padres' current free agents, Gary Sanchez has become the one with which a reunion with San Diego is the most likely. After bouncing around the league following a seven season rollercoaster stint with the Yankees, Sanchez ended up landing with the Padres when they claimed him off waivers in May 2023 from the Mets.
A broken wrist cut Sanchez's 2023 season short, but he played reasonably well in the 72 games he did play for the Padres last season including cracking 19 homers. San Diego is interested in a reunion, but it doesn't look like the sides are close to a deal at the moment.