The Phillies' surprising and ultimately unnecessary signing of first baseman Carlos Santana to a three-year, $60 million contract in December 2017 is still affecting them three years later.
The Phils' front office decided that winter that Santana was what the offense needed and made the move, even though it meant shifting Rhys Hoskins to left field, a position it was unclear he could play regularly.
After one season, the experiment ended. The Phillies had the worst outfield defense in MLB in 2018 with minus-45 Defensive Runs Saved. Santana walked 110 times but hit .229 and slugged just .414, lower than Odubel Herrera or Nick Williams.
The idea didn't work. But $35 million was still owed to Santana and it was clear that Hoskins needed to move back to first base. So ... what?
Fortunately for the Phillies, the Jean Segura trade materialized. They sent Santana and then-23-year-old J.P. Crawford to Seattle for Segura and relievers Juan Nicasio and James Pazos.
The Phillies cleared their self-inflicted first-base logjam and made a short-term upgrade at shortstop in that move. But it cost them. Santana had two years and $35 million remaining on his contract at that time. Segura had four years and $59 million. Nicasio had one year at $9 million. The teams swapped contracts and about $32 million was shifted from the Mariners' future books to the Phillies'.
The Phillies pretty much doubled their remaining expenditure in order to rearrange their roster in a way that made sense.
In two seasons with the Phillies, Segura has been decent but unspectacular. He's essentially performed to his career levels, hitting for a bit less average with a bit more pop. He's hit .298 with runners in scoring position each season and had a handful of game-winning hits and/or clutch moments, particularly against the Mets.
Segura is under contract for two more years and is owed a total of $29.5 million. It's not an exorbitant sum for a versatile infielder who is an above-average offensive performer. But in a pandemic year, with billions gone from the game and so many jobs lost, it takes on a different look.
Meanwhile, Didi Gregorius, who joined the Phillies last offseason on a one-year, $14 million deal, is a free agent again after a consistent and dynamic summer. He led the Phillies with 61 hits and 40 RBI. He hit .284 with 10 doubles, 10 homers and an .827 OPS. He hit .345 with runners in scoring position.
If the Phillies could choose between Segura or the player they signed to move Segura off of shortstop, they'd choose Gregorius. They are the same age but Gregorius can be a far more impactful offensive player.
Will the Phillies be able to re-sign him? This offseason is impossible to predict. In a normal winter, Gregorius would be in line for a four- or five-year contract for about $15 million per year. Something like five years, $75 million, or four years at that AAV with an option.
This is when the Phillies are feeling the financial impact of that Santana-Segura trade. Santana's contract has expired. Segura, for two more years, still earns $15 million annually. That's $15 million the Phillies probably wish they could reallocate toward the better shortstop and hitter. They still could re-sign Gregorius and have them both, it's just trickier with J.T. Realmuto also being a free agent and the glaring need to upgrade the pitching staff in a substantive way.
It is possible that Gregorius does not find that $15 million AAV over four or five years this offseason. It's possible that some (or more than some) teams sit out the multi-year tier of free agency because of their financial losses.