The 2023 offseason has begun earlier than the Philadelphia Phillies wanted it to. Aaron Nola is anticipating free agency this winter instead of looking forward to a chance to solidify his Philadelphia legacy with a memorable performance in the World Series.

Dave Dombrowski faces key decisions to patch up a roster that came up small in the biggest moments against the Arizona Diamondbacks. He needs to address a crossroad at the top of the starting rotation, a shuffle between power hitters on the current roster, and weaknesses in the bullpen and on the bench.

The Bryce Harper Effect
Bryce Harper began the 2022 season recovering from offseason Tommy John surgery. He not only returned surprisingly earlier than his original timeline suggested, but he also began playing a new position.

The $330 million man showed his natural athleticism and competitive spirit with an excellent transition to 1st base. Will he return to right field? How will his decision affect the future of Rhys Hoskins and Nick Castellanos?

The plans of the organization will hinge on Harper, their superstar and offensive centerpiece.

Bench, Bullpen, Secondary Decisions
All contending teams look to make changes to improve their bullpen and bench. The Phillies brought in Gregory Soto and Craig Kimbel last offseason. They made tweaks to their bench during Spring Training and after the start of the 2023 regular season.

Another starting pitcher threw an additional curveball into the situation after the NLCS. Taijuan Walker didn’t appear in a postseason game. He still made his presence known with an unnecessarily strong social media stance against Rob Thomson. Now, Aaron Nola in free agency isn’t the only question among the starters.

The Phillies no longer have the aftermath of positively that resulted from a miracle run to the World Series in 2022.

They now face the pressure of a stunning playoff exit and a closing window of opportunity to deliver a championship to Philadelphia. How will they handle it?

Aaron Nola

Aaron Nola entering free agency will be the biggest and most impactful offseason storyline for the Phillies. A contract extension looked like an obvious decision one year ago.

However, the organization cut off negotiations with Nola’s camp during Spring Training in March 2023 because they couldn’t agree on the veteran righty’s value. Is it reasonable to expect negotiations to go any better after Nola’s underwhelming season in 2023?

Jayson Stark joined The Best Show Ever to talk about the crucial decision.

“In a really bad free agent market, he could get seven years, $200 million, 220, 240, I don’t know what. The (Stephen) Strasburg contract was seven (years), $235 (million). None of that is out of the question because I know how other teams value him, how they see him. Are the Phillies going to give him that?” -Jayson Stark

Nola represented the climb the Phillies made from a disastrous rebuild under Matt Klentak to a National League pennant in 2022. He was one of the few homegrown players who survived the same stretch that fans had endured.

He also owns the best opponent batting average (.231) and the fifth-best WHIP (1.13) among all qualified Phillies pitchers throughout the past 140 years. He sits fifth in strikeouts and seventh in starts. The former LSU star finished third in NL Cy Young voting in 2018 and fourth in 2022.

The overall body of work shouldn’t be ignored. The organization saw his value once again in his first three starts of the 2023 playoffs.

However, the Phillies need to make the tough decision on a pitcher at age 30 coming off a poor regular season who will cost serious money over a significant term.

If the Phillies do let Nola walk away, they must find a starting pitcher to pair with Zack Wheeler at the top of the rotation. Stark mentioned the possibility that Dombrowski could pursue Corbin Burnes on the trade market.

Who could the Phillies send to the Milwaukee Brewers for a pitcher only two years removed from a Cy Young Award? Nick Castellanos surprisingly came up in the conversation as a potential trade chip.

Nick Castellanos

It’s amazing how quickly things can change in professional sports.

Nick Castellanos was a hero in Philadelphia after the NLDS victory against the Atlanta Braves. He became the first player in MLB history with two consecutive multi-home run games in the postseason.

Now, he might be the odd man out in the outfield shuffle that hinges on Harper’s decision.

If the best situation for Harper is to move to 1st base long term, the Phillies would become more likely to let Rhys Hoskins walk away in free agency. If he moves back to right field, how does it affect the lineup? Castellanos had an excellent bounce-back season in 2023, and he is under contract for three more seasons.

He brings power that adds to any major league lineup, but the expensive contract makes him less valuable in trade negotiations.

Castellanos will turn 32 during Spring Training. It would be a shame to see him and his extremely entertaining son leave town, but it might be a necessary part of the big picture. His future hangs in the balance based on Harper and Nola’s future.

Rhys Hoskins
Rhys Hoskins, Philadelphia PhilliesPhoto by Sarah Stier/Getty Images

Things haven’t always been the smoothest with Rhys Hoskins in Philadelphia, but the fans showed their appreciation for an ultimately accepted and in some ways beloved player when he threw out the first pitch of the playoff opener at Citizens Bank Park.

He deserves every bit of appreciation he got after missing the entirety of the final season of his contract with a torn ACL.

The long-time Phillies slugger will turn 31 during Spring Training. Harper stepped into a position he’d never played and added value with a significantly higher level of defense than Hoskins.

Kyle Schwarber also figures into the organization’s future as the designated hitter much more significantly.

If the Phillies ultimately move Castellanos or make another splashy offseason shakeup, Hoskins could be a cheap option to sure up the lineup with some pop.

He finished each of his first five seasons in red pinstripes with an OPS over .800 and his sixth in 2022 just a tick lower at .794. It’s reasonable to expect him to approach 30 home runs in a full-time role if he stays healthy.

Speculation that he could’ve returned for the (expected) World Series suggests that he is on track for a full recovery. Since the untimely injury, it’s looked like Hoskins’ run in Philadelphia is over.

The slugger is more likely to walk away, but don’t close the door just yet.

Craig Kimbrel

It sounds unusual for a future Hall of Famer who closed the All-Star Game after an excellent first half. Craig Kimbrel almost certainly won’t return to Philadelphia.

He didn’t look as sharp down the stretch despite a statistically successful September when he didn’t allow an earned run in 10 of 12 appearances. He even began the playoffs with four scoreless appearances.

The bottom fell out during the NLCS. He took the loss in Game 3 after allowing a walk-off single to Ketel Marte. His biggest gaffe came in Game 4 when he blew a 5-3 lead in a game that ultimately let the Diamondbacks take momentum in the series.

He was a short-term solution at the back end of the bullpen, but the Phillies should not retain Kimbrel for the 2024 season.

Edmundo Sosa
Edmundo Sosa, Philadelphia PhilliesPhoto by Tim Nwachukwu/Getty Images

Edmundo Sosa’s time in Philadelphia got off to a good start. He was a reliable bench player during the run to the 2022 World Series, and he looked like he could help patch the hole left by Rhys Hoskins early in the 2023 season. However, he didn’t provide as much value with the glove as the Phillies hoped for.

He is eligible for arbitration during the 2024 offseason, and the Phillies should be able to upgrade a bench that made minimal contributions.

Jake Cave
Jake Cave, Philadelphia Phillies

When the Diamondbacks recorded the final out of the 2023 NLCS, Jake Cave breathed a sigh of a broken dream after he couldn’t come up with a way to extend the game.

He’s the prototypical AAAA player who can potentially provide value with some pop off the bench. He showed some of it for the Lehigh Valley IronPigs in 2023, but it didn’t translate enough in 65 games with the Phillies.

They should look to upgrade with a left-handed bat off the bench.

Jeff Hoffman
Jeff Hoffman, Philadelphia PhilliesPhoto by Elsa/Getty Images

The Phillies should look at retaining Jeff Hoffman as a priority during the offseason. He posted his best ERA and a career-high 52 appearances in his eighth major league season in 2023.

While the top right-handed options in the Philadelphia bullpen faded by the end of the NLCS, Hoffman stood tall. He held opponents scoreless in seven of eight playoff appearances.

He is eligible for arbitration, and he should be relatively affordable with an estimated salary of $3-4 million. Dombrowski must do what he can to bring Hoffman back.

Taijuan Walker

Rob Thomson clearly had no faith in Taijuan Walker during the postseason. The former New York Mets righty signed a four-year, $72 million contract entering the 2023 season.

He proved himself unreliable with a 7.15 ERA in the 1st inning in 31 starts.

The Phillies shouldn’t want a player on their roster who reacts to a heartbreaking playoff loss by criticizing his manager on social media. Walker also liked tweets from fans with even more vehement language than he used.

Will he stay with the team? Will anyone take an average (at best) pitcher with that kind of salary off their hands? Probably not.