1) Jameson Taillon
Over the 2022 offseason, the Cubs signed a huge free agent class, including several players on this list. Jameson Taillon stands head and shoulders above the rest as the worst signing of the bunch, and likely the worst contract in the division as a whole. Taillon stands a chance of reaching that true worst-case scenario: a scenario in which he is cut from the team.
The signing didn't look quite so terrible at the moment, though it wasn't exactly brilliant. After debuting with Pittsburgh in 2016, Taillon enjoyed four strong seasons with the Pirates. After missing all of 2020, Taillon resurfaced with the Yankees, where he posted two solid, albeit unspectacular, seasons. Taillon proved to be a fairly durable Yankee, making 61 starts and eating 321.2 innings over the course of the 2021 and 2022 seasons. His 4.08 ERA in that time was almost exactly league average.
The Cubs believed Taillon had room to improve, and perhaps saw the opportunity to buy low on a pitcher who had shown considerable upside at times in Pittsburgh. Unfortunately for them, he has regressed in every way. After signing his four-year $68MM contract, Taillon has produced dreadful results. In 21 starts, Taillon has covered just 104 innings and has recorded an ERA of 5.71. Few pitchers with as many innings have posted worse results. Taillon's walk rate is slightly elevated, but it;'s the inflated home run rate that has rendered him completely ineffective. To some extent, Taillon has always struggled to prevent the long ball, though those struggles have climaxed in 2023, as he has allowed 17 already.
The Cubs will have him under contract until the end of the 2026 season, at which point Taillon will become a free agent. Over the remaining three full seasons, Taillon is owed $54MM, which will be split equally over the next three seasons. With so much time left on the contract, it remains possible that Taillon bounces back and helps the Cubs salvage some value. Such a development would certainly be welcome in Wrigleyville, but it's unlikely.
On the flip side, Taillon may continue to regress, which could further inflate his numbers, eventually leaving the team with no option other than to designate him for assignment. The high dollar amount (at least for this division), the current level of production, and the remaining years of this deal make it the worst in the division.