Trade Deadline Smash or Pass: Josh Naylor

Naylor could add some thump to the lineup, at a first base position that has taken a step back offensively over the past month.

It’s time for more Smash or Pass, trade deadline edition! In the run-up to the trade deadline, we’ll take a look at some potential targets and discuss whether they make sense for the Red Sox. First up: a power-hitting first baseman.

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Who is he and where does he come from?

Josh Naylor was drafted in 2015 by the Miami Marlins with the 12th overall pick and has been involved in a few notable trades since then. At the trade deadline in 2016 he was sent to San Diego alongside pitcher Luis Castillo in return for the immortal Andrew Cashner. At the 2020 deadline, San Diego traded Naylor to Cleveland along with a haul of prospects (Gabriel Arias, Joey Cantillo, Austin Hedges, Owen Miller, and Cal Quantrill) for, essentially, Mike Clevinger. Before the 2025 season, in the final year of his contract, Naylor was moved to Arizona, where he hits cleanup and mashes baseballs on a nightly basis, in return for pitcher Slade Cecconi.

Is he available?

You’d have to think so. The Diamondbacks enter play Wednesday with a 50-52 record. They’re six games behind the final Wild Card spot (in the loss column), and would need to pass the Reds, Cardinals, Giants, and Padres to get there. Fangraphs gives them a 13% chance to make the playoffs. Since the Diamondbacks have numerous players entering free agency, including Naylor, Eugenio Suarez, Zac Gallen, and Merrill Kelly, as well as some core players to build around, it seems like a no-brainer for Arizona to “re-tool” for 2026.

Is he any good?

Offensively, he has been a difference-maker since 2022 as a power-hitting bat, with his biggest season coming in 2024, when he hit 31 home runs and drove in 108 runs for Cleveland. This season, Naylor is hitting .293, and he also had a .308 average in 2023. Shockingly, Naylor is 11-for-13 stealing bases this year, a career high for a player who has a third percentile Sprint Speed. His plate discipline has been great this year, with a 92nd percentile K-rate of 12.6% and a strong 9.5% BB-rate.

As a pull-heavy fly ball hitter, he’ll need to get a hold of balls to put them out of Fenway to right field. Naylor has averaged a strong 28 doubles a season since 2022, which could see an uptick if a few flyballs don’t reach the bullpen. All of his 11 home runs in 2025 are to center and right field, although in 2024, he dispersed his 31 bombs a bit more.

Baseball Savant

Defensively, Naylor has a negative-3 OAA in 2025, which is in the 18th percentile. However, he has committed just four errors on the season, and Naylor was a positive in Outs Above Average in each of the previous three seasons.

Why would he be a good fit for the Red Sox?

He would be a perfect fit, in my mind. Just look at this behavior. People will love Josh Naylor here.

Watching this team play night after night, it feels like they need another power-hitting bat and first base is a position in which you are expecting to get some power. Boston ranks 19th in home runs at 1B this season (13), and when they entered the season with Triston Casas manning the position, the hope was for much better than that. As much as I’ve appreciated the contributions of Abraham Toro, he has a .221 BA, 55 wRC+, and .042 ISO over the past six weeks, and it’s a clear spot that can use an upgrade.

Financially, the Red Sox can take on Naylor’s remaining salary with no issue. You may have heard that they cleared some salary off the books back in June. Per @RedSoxPayroll on Twitter, the team is currently at $247.7M, which is $13.3M away from the second Luxury Tax threshold. Naylor has $3.5M prorated of a $10.9M salary remaining this season. Kelly has $2.2M remaining and Gallen has $4.3M remaining. A combination of any two of these players would not threaten that threshold.

Why would he not be a good fit for the Red Sox?

The one drawback for Naylor is the fact that he hits left-handed. In his career, Naylor hits for a .240 batting average with a .368 SLG vs. LHP, as opposed to a .277 average and a .473 SLG vs. RHP. In 2025 only, the split is .259 (.362 SLG) vs. LHP, against .310 (.493 SLG) vs RHP.

What would it cost?

Of the four soon-to-be-free agents mentioned above (Suarez, Gallen, Kelly, and Naylor) it’s reasonable to think that Naylor would be the most affordable of the bunch. Suarez seems likely to land with the Yankees or the Cubs. For as putrid of a season as Gallen is having, he and Kelly would probably fetch a strong return, as so few starting pitchers with any kind of track record will be available. From 2022 to 2024, Gallen was 43-19 with a 3.20 ERA and a 1.09 WHIP, including two top-5 Cy Young seasons. He has inexplicably put up a 5.58 ERA in 2025 over 21 starts, the worst ERA in all of MLB, while leading the NL in home runs allowed. Kelly is 9-5 with a 3.32 over 21 starts, and sports a 3.76 career ERA. If Boston is going to send out one of their top five prospects, such as Franklin Arias, Jhostynxon Garcia, or Luis Perales, Boston will probably try to trade for either Kelly or Gallen, along with Naylor.

If Naylor is coming over as a single piece, I would think a player from the next tier of prospects could land him. Using Sox Prospects as a guide, a player like James Tibbs, Connelly Early, or David Sandlin should all be MLB-ready within a year or so. Pairing one of them with another top-20 prospect seems reasonable.

The Athletic listed Naylor as the #17 player available at the trade deadline on their “Big Board” that was updated today. After seeing a free agency period in which Pete Alonso received 2 years for $54M, and Christian Walker got 3-for-$60M, first basemen are simply not in demand the same way they were even three years ago, especially if they don’t offer much defensively.

Smash or Pass?

While I understand that “pitching, pitching, pitching” is the first thing on everyone’s mind, I have a feeling that the cost will be prohibitive to part with a top prospect, or Jarren Duran, or Wilyer Abreu, unless it is for a controllable arm. If Joe Ryan is the return, then by all means, go nuts.

If the team can add Josh Naylor as an improvement at first base, as well as get an arm in the next tier, then I think it will look like a serious playoff contender. Fortunately, Arizona has both of these things, and a Naylor/Kelly package makes a lot of sense for Boston. Naylor has playoff experience and has a serious bit of “crazy” to him that I think this team would embrace down the stretch, and hopefully into the playoffs.

Smash!