Can teams find a true upgrade at shortstop this winter? As the regular season winds down, MLBTR is cataloguing every position for the 2026‑27 free‑agent market, and shortstop tops the list. This year’s pool is thin, dominated by rebound hopes and versatile swingmen.
Ages reflect the 2027 season; names within each tier appear alphabetically, not by rank. Only players who saw MLB action or spent time on a 60‑day injured list this year are counted.
Previous entries in this series: Catcher, First Base, Second Base, Third Base.
J.P. Crawford (32)
Crawford once shone as a plus‑defensive shortstop, but 2026‑27 finds him past his peak. Over 706 innings at the position he posted –12 DRS and –13 OAA, and he committed five throwing errors, a spike likely tied to shoulder, wrist and hand injuries. Those ailments also suppress his range numbers, even if Statcast still flags limited foot speed.
At the plate he offers a low average but a solid on‑base skill set, walking 11.6% of career PA and maintaining at least an 11.3% walk rate the past five years. This season he’s up to 13.3%, batting .218/.334/.344. A .251 BABIP and a rise in infield pop‑ups (20 this year, second‑most of his career) explain the dip in average.
For my money, Crawford’s clubhouse leadership outweighs his declining glove. Seattle fans sing his praises, and his willingness to shift to third base to clear the way for Colt Emerson shows the kind of teammate he is.
Mauricio Dubón (32)
Dubón belongs more in the utility pool, yet his winter numbers—.276/.321/.395 with career‑best plate appearances (612), homers (11), doubles (28), triples (3) and steals (10)—make him a viable shortstop option. He lacks raw power (86.4 mph exit, 29.2% hard‑hit rate) but compensates with elite contact; his 11.9% strikeout rate ranks tenth‑lowest among qualified hitters. Walks are scarce and unlikely to improve.
Although he’s never anchored a lineup at shortstop, there’s no reason he couldn’t handle the role for a season or two. A two‑year contract is improbable; instead, teams may use him as a one‑year bridge or a part‑time stopgap while grooming a prospect. Many will still target his jack‑of‑all‑trades value.
Isiah Kiner‑Falefa (32)
Kiner‑Falefa mirrors Dubón in versatility but boasts superior contact and on‑base skills. His strikeout rate sits between 15‑17%, well under the league average, while his walk rate spikes to 9.8% in a small 173‑PA sample—likely an outlier given his historic 3.5% walk pace. Chase and swing rates remain consistent with his 2024‑25 performance.
Defensively he can man shortstop, second and third with competence, and even serve as an emergency catcher. At the plate he’s .242/.318/.314 over 173 PA this year. He deserves a major‑league deal, probably a one‑year contract with less guarantee than the $6 MM Boston paid.
Edmundo Sosa (31)
Sosa’s season resembled a roller coaster: rough patches in May and July, average output in April and June, then a scorching finish in August‑September. Overall, his 2026 line (.247/.285/.417) trails league average but isn’t disastrous, and it sits close to his combined 2023‑25 pace (.261/.301/.438).
A right‑handed hitter, Sosa thrives against lefties, struggles versus righties, and can fill every corner of the diamond. He carries plus defensive marks at second, short and third, and has logged limited left‑field work plus three innings in center as an emergency option.
Ha‑Seong Kim (31)
Kim’s shoulder surgery late in 2024 still haunts his performance. After a two‑year, $29 MM deal with Tampa Bay and a brief waiver claim by Atlanta, he signed a $20 MM contract after rejecting a $16 MM player option. The comeback lagged, and his numbers collapsed.
He’s now among the league’s least productive hitters, posting .113/.203/.121 over 139 PA and a wRC+ of –4, the third‑worst single‑season mark (min 130 PA) in the past decade, behind only Cam Gallagher (2023) and Trayce Thompson (2018).
Kim’s fall is shocking; once a potential nine‑figure shortstop, he never became a great hitter but posted a respectable .250/.336/.385 line from 2022‑24. At 30 (31 in weeks), he could still rebound on a cheap one‑year or minor‑league deal, especially if he stays healthy.
Is the Class Thin Enough…?
Jazz Chisholm Jr. (29)
I’m not pretending this is a likely move, but when options dwindle teams might think outside the box. Chisholm hasn’t played shortstop since 2021, logging only 330 innings there with modest grades. He bounced between middle infield spots in Seattle before shifting to center field, then back to second base by 2025.
His defense at second remains solid; a –6 DRS this year is his only negative metric, while Statcast’s 13 OAA suggests he’s still effective. Offensively he could still hit 20 homers and steal 40 bases, though injuries have dulled his overall output.
The most probable scenario sees Chisholm signing elsewhere as a second‑baseman, yet stranger outcomes have occurred—recall Luis Arraez’s surprise switch to second and his defensive surge. If Chisholm entertained a one‑year, opt‑out‑heavy deal to test shortstop, the gamble would be huge, and I’d love to claim I predicted it.
Orlando Arcia (32), Paul DeJong (33), Kyle Farmer (35), Nick Madrigal (30), Jorge Mateo (32), Brendan Rodgers (30), Ramón Urías (33)
Bo Bichette (29): Can opt out of remaining two years, $84 MM (would receive $5 MM buyout for opting out; contract allows Bichette to opt out next winter as well)
Bichette’s rough start still drags his stats, but he’s rebounded since early June. In just over 400 PA he’s .289/.335/.441 with 12 homers, 18 doubles, two triples, a 6.7% walk rate and a 19.3% strikeout rate—close to his career .294/.337/.469 line, yet shy of last year’s peak pace.
Even with the early slump, opting out could net him more than the net $79 MM he’d leave behind, though the upside isn’t guaranteed. Staying might be wiser: collect $42 MM next season, hope for a breakout, then consider another opt‑out when the buyout hits. A big rebound could set up another nine‑figure contract.
Whether any club views Bichette as a genuine shortstop solution is debatable. The Mets gave him occasional time at the position when Lindor was unavailable, but few teams will eagerly plug him in full‑time. He’ll likely abandon the opt‑out, rendering the scenario moot.