The Philadelphia Phillies have made some questionable free agent signings over the last couple of years. While the organization has been a playoff contender for a few seasons now, there have been some free agent signings dating back to 2018 that have not panned out as the front office envisioned.
While the most recent signings are fresh in our memories, what are some other bad decisions the Phillies have made with their free agent additions since 2018?
Here are the nine worst free agent signings the Phillies have made over the last seven years
Jake Arrieta, RHP
Starting pitcher Jake Arrieta was a part of contending teams with the Chicago Cubs before he signed a three-year, $75 million contract with Philadelphia in March 2018. After one of his Phillies starts, a loss to the San Francisco Giants, he was critical of his teammates and thought they lacked accountability for their poor play. It is questionable how much Arrieta's harsh disposition inspired the rest of the roster to play better.
The starter admitted in spring training for the 2019 season that he played with a knee injury and chose not to tell teammates or manager Gabe Kapler. Arrieta was on a decline during his time with the franchise. This was evident during his lack of production in 2019 and the shortened 2020 season. He went 22-23 with a 4.36 ERA in 64 starts over his three seasons as a Phillie.
Didi Gregorius, SS
The Phillies signed Didi Gregorius to a one-year, $14 million contract in December 2019. Gregorius had a productive first year with Philadelphia in 2020. As a result, they re-signed him to a two-year, $28 million deal in January 2021. The following year, he only played in 103 games due to an elbow injury. The veteran shortstop finished with a slash line of .209/.270/.370. He dealt with a knee sprain in 2022, his final year in the majors.
Due to the emergence of Bryson Stott while Gregorius was on the IL, the Phillies ended up releasing the infielder at the beginning of August in 2022. Gregorius played in 63 games and had a .567 OPS along with a .210/.263/.304 line.
Jeurys Familia, RHP
Jeurys Familia signed with the Phillies before the 2022 season to a one-year, $6 million contract. He performed satisfactorily during April and May. He entered June with a 3.79 ERA, but it increased to 5.13 at the beginning of July. It rose to 6.09 before the team released him at the beginning of August after they designated him for assignment.
Familia was unable to replicate the same sort of success with Philly that he demonstrated with the New York Mets. Multiple Phillies relievers outperformed him. The trade deadline addition of David Robertson signified the end of Familia's short stint with Philadelphia.
Nick Castellanos, OF
The Phillies added outfielder Nick Castellanos on a five-year, $100 million contract in March 2022. It is one of the club's contracts that has not been viewed as a great decision by the organization based on his play. He has been mentioned in trade rumors the last few offseasons.
Recently, manager Rob Thomson has relegated Castellanos to be part of an outfield rotation. The right fielder is frequently getting days off, which was not the case in either of the last two seasons. He did not do well offensively in July and August and expressed his displeasure at Thomson's decision to remove him for a defensive replacement on August 30. Whether he is traded or not is on track to be an offseason topic again.
Taijuan Walker, RHP
The acquisition of Taijuan Walker before the 2023 season looked like it would strengthen the Phillies' starting rotation. He finished with 15 wins in 31 starts despite compiling a career-high 71 walks. The right-hander voiced his displeasure with not making the club's postseason roster.
The 2024 season was even more of a struggle as he missed time with injuries. Thomson moved Walker to the bullpen later in the regular season and the veteran was once again not a member of the playoff roster. Walker has been far too unpredictable on the mound during his tenure to warrant the four-year, $72 million deal the Phillies signed him to.
Whit Merrifield, UTIL
Philly signed Whit Merrifield to a one-year, $8 million contract before the 2024 season. He looked to be a solid signing for Philadelphia's depth during spring training last year. However, he did not adjust well at all to being in a reserve role and did not do well offensively for the Phillies as he had a .184/.266/.286 slash line entering June.
The experienced utility player had trouble transitioning to Philadelphia following a year in which he made the All-Star Game as a member of the Toronto Blue Jays. The Phillies released him in the middle of July. He finished with a .199/.277/.295 line and a .572 OPS in 53 contests.
Jordan Romano, RHP
Philadelphia signed Jordan Romano to a one-year, $8.5 million contract ahead of the 2025 season. His short time with the Phillies has been disappointing. Originally viewed as a ninth-inning option, the right-hander has not been used in this role for some time and has an alarming 8.23 ERA in 49 games.
Romano allowed a home run and four earned runs in one inning on Aug. 25 versus the Mets. The Phillies placed him on the 15-day IL with right middle finger inflammation the following day. He is in danger of losing his roster spot before the end of the regular season. The 32-year-old should not make the postseason roster.
Max Kepler, OF
The Phillies added Max Kepler to their outfield group in free agency on a one-year, $10 million deal in December 2024. He has not given the team any reason to consider bringing him back on a new contract this offseason. The 32-year-old entered August with a .203/.297/.357 line and an OPS of .654.
Kepler had a good month of August with an .802 OPS and a slash line of .298/.313/.489. However, he is a part of the outfield rotation and won't be playing every game. It would not be surprising if he reverted to his offensive struggles before the end of the regular season.
Joe Ross, RHP
Joe Ross agreed to a one-year, $4 million deal with the Phillies in the 2024-2025 offseason. He did not do as well as anticipated, as he dealt with inconsistency in April. The right-hander missed some time from the end of July until the beginning of August with back spasms.
Ross appeared in the first contest of the three-game series versus the Mets on Aug. 25. He allowed three earned runs in one inning and the Phillies ended up releasing him the next day. He finished his Phillies career with a 5.12 ERA over 51 innings in 37 contests.