As Phillies fans hope that the team has another big move left in them (Don’t hold your breath!), I decided to take a look at recent offseasons to see how many big moves they’ve made closer to the start of camp. Then, as one does, I decided to make the exercise into an interactive March Madness-style tournament.
From 2010 to 2025, I identified the last free agent the team signed before the season began. To qualify for the list, the player:
- Had to be an outside signing. Re-signings like J.T. Realmuto in 2021 do not count, but former Phillies who were on a different team in between (Cliff Lee) do qualify.
- The player had to appear in at least one game the season he was signed.
Here’s the field, seeded by WAR in their first season with the team:
- Cliff Lee 2011
- Bryce Harper 2019
- Jake Arrieta 2018
- Jeff Hoffman 2023
- Jose Contreras 2010
- Brad Miller 2021
- Luis Garcia 2013
- Joe Ross 2025
- Nick Castellanos 2022
- David Lough 2016
- Neil Walker 2020
- Ronny Cedeño 2014
- Chad Qualls 2012
- Ricardo Pinto 2024
- Dustin McGowan 2015
- Michael Saunders 2017
Some of those names you’ll recognize (even if you wish you didn’t), and some you’ll probably need a refresher on.
Twice a week, I’ll present a matchup, and the readers will get to vote for which player should advance. You can choose to vote for the player who had the best initial season, the player who has had the best Phillies career, a player you have a soft spot for (Where my Qualls-heads at?), or simply vote for chaos and let Nick Castellanos win it all as a farewell(?) present.
We’ll start things off with our 8-9 matchup. Here’s a quick summary:
8. Joe Ross, 2025
Stats with the Phillies: 37 games, 51 IP, 2-1, 5.12 ERA, 39 K, 18 BB, 0.0 WAR
After a solid season as a swingman for the Brewers in 2024, the Phillies signed Joe Ross hoping he could provide both rotation depth as well as solid middle relief. As it turned out, Taijuan Walker filled the rotation depth role, so Ross was kept in the bullpen all year. However, he wasn’t very good there, putting up an ERA over 5, and he was eventually released in August.
9. Nick Castellanos 2022
Stats with the Phillies: 602 games, .260/.306/.426, 82 HR, 326 RBI, 1.3 WAR
After the lockout ended in 2022, it appeared that Kyle Schwarber was going to be the Phillies’ big free agent signing of the year. But with Nick Castellanos lingering on the free agent market, the Phillies decided to splurge and add him to their outfield.
Coming off a career best year, Castellanos struggled mightily in his first season for the Phillies. Things improved after that, but not nearly enough to justify his contract. While there were some highlights during his tenure, it’s been a mostly disappointing four years, and it’s only a matter of time before he’s released by the team.
