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The most recent offseason featured a huge crop of star free agents, with the five top-tier shortstops being one of the most exciting elements, as Corey Seager, Carlos Correa, Marcus Semien, Javier Baez and Trevor Story all reached the open market at the same time. In about five months’ time, another offseason will begin, and although the crop of available shortstops won’t be quite as strong, it still has the potential to be noteworthy.

MLBTR recently released its first free-agent power rankings for the upcoming winter, and although red-hot outfielder Aaron Judge nabbed the top spot, he was followed by three shortstops in the 2, 3 and 4 slots: Carlos Correa, Trea Turner and Xander Bogaerts. (Correa and Bogaerts both have opt-outs that they are expected to trigger.) In Sunday’s column from Bob Nightengale of USA Today, he reports that the Cubs could be big spenders this winter, naming those three shortstops as their primary targets. “I guarantee you they’re going to get one of them,” an unnamed veteran general manager tells Nightengale, who also says that several executives are predicting the Phillies to be sitting at this table as well.

Cubs manager David Ross recently spoke about letting Nico Hoerner serve as the team’s primary shortstop for the remainder of the year, but he’s also spent a decent amount of time at second base as well as occasionally lining up at third base and in the outfield. It seems the club may be leaning toward a big addition at shortstop and bumping Hoerner over to second base next year.

After a big trade-deadline fire sale in 2021, the Cubs were expected to have a fairly quiet offseason this past winter. However, they surprised many people by making a few somewhat aggressive moves. They didn’t land any of the big five shortstops, but they did give out multiyear deals to Seiya Suzuki, Marcus Stroman and Yan Gomes.

The club is currently sporting a record of 23-31, six games back of the final playoff spot. There’s still time for them to gain some ground, but it’s also possible they go into the trade deadline as sellers this year. But regardless of how they fare for the remainder of this season, they should have spending power this winter. Suzuki is the only player currently under contract for the 2025 season, but the Cubs also have a $7M club option for David Bote that year. Stroman’s contract runs through 2024, but he can opt out after the 2023 season. Kyle Hendricks and Yan Gomes could also be free agents after 2023, as they have options for 2024.

In short, there’s not a lot preventing the club from making a big splash this winter if they want to. According to Cot’s Baseball Contracts, the team ran out Opening Day payrolls in the vicinity of $200M from 2016 to 2019, but got that number below $150M last year and this year. Jason Martinez of Roster Resource pegs their 2023 payroll at $94M at the moment, then just $50M in 2024 and $20M in 2025. Arbitration-eligible players will add to those numbers, but not by a lot. If they want to be aggressive in getting out of this rebuild/retool/whatever period, the opportunity is there.

The Phillies, however, are in a very different situation. They had a very aggressive offseason, giving out big contracts to both Nick Castellanos and Kyle Schwarber, pushing the club beyond the luxury-tax line for the first time. Despite that aggressiveness, they’ve struggled over the first third of the season, going into Sunday’s action with a record of 24-29, 4.5 games behind the Giants for the final NL wild-card spot.

There was some speculation that they would dive into the shortstop sweepstakes this past winter, but they ultimately decided to stick with the in-house options of Didi Gregorius and prospect Bryson Stott. Gregorius is currently on the IL due to a sprained knee, but was performing OK before that. His .288/.338/.356 line amounts to a 97 wRC+, slightly below league average but much better than the 68 wRC+ he had last year. Regardless, he’s a free agent after this year, giving the club an opening next year. Stott could theoretically fill that void, but he’s struggled in his first taste of MLB action. Through 27 games, he’s hitting just .157/.222/.217 for a wRC+ of just 26. If the Phils were to go out and nab a big fish in free agency, Stott could spend more time in the minors or perhaps shift over to another infield position to try to force his way into the lineup, having played some second and third base as well.

Despite getting into luxury-tax territory this year, the club should be able to be aggressive again next winter with many contracts coming off the books. Martinez puts their 2023 payroll at $129M, well shy of this year’s $232M, but that doesn’t include a $17M option for Jean Segura, the $16M option for Aaron Nola or salaries for arbitration-eligible players, including Rhys Hoskins. Regardless of whether they can turn their 2022 season around, it seems they may keep their foot on the gas pedal going forward, as they look to snap a postseason drought that goes back to 2011.

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