White Sox Sign LHP Anthony Kay, Eye Outfield Help Next: Three Free Agent Fits to Watch

The White Sox made their first move of the offseason this week, signing left-handed pitcher Anthony Kay to a two-year deal. It’s a solid start for a team that needed to add a southpaw to its rotation, but it’s far from the only box that needs checking this winter.

With the recent decision to non-tender outfielder Mike Tauchman, the outfield depth chart has thinned out considerably. Andrew Benintendi’s ongoing health concerns only add to the uncertainty, and with his future in Chicago looking murky, the Sox are clearly in the market for outfield help.

Let’s break down three potential free agent outfielders who could be on the White Sox radar – and whether they make sense for a club that needs both production and flexibility in its lineup.

Rob Refsnyder: The Platoon Option with a Purpose

At 35, Rob Refsnyder isn’t going to headline any offseason splash, but there’s a lot to like about what he brings to the table – especially for a team like the White Sox that could use a right-handed bat to pair with a lefty like Benintendi.

Refsnyder has quietly put together back-to-back seasons with an OPS north of .825, thriving in a platoon role where he’s consistently punished left-handed pitching. His approach at the plate has aged well – he posted an 11.5% walk rate in 2025 – and while he’s not a power threat, he’s shown he can run into one now and then, with 20 homers over the past two seasons.

Defensively, he’s not flashy, but he holds his own. He grades out around league average in the outfield and still has a solid arm.

At this stage in his career, Refsnyder is exactly the kind of inexpensive, low-risk veteran who can give you quality at-bats off the bench or in a platoon role. If the White Sox are planning to bring in multiple outfielders this offseason – and they should – Refsnyder makes a lot of sense as part of that equation.

Verdict: Target

Max Kepler: A Familiar Foe, Now a Potential Fit?

White Sox fans know Max Kepler well – and not always fondly – from his decade-long run with the division-rival Twins. After a down year in Minnesota in 2024, he signed with the Phillies, hoping to bounce back.

That bounce never really came. He finished 2025 with a .691 OPS and just eight home runs, marking his second straight subpar season.

But here’s where it gets interesting: despite the surface-level struggles, Kepler’s underlying metrics in 2025 told a slightly different story. His chase rate, hard-hit rate, and exit velocities were all above league average. That suggests there’s still some life in the bat – even if the results haven’t shown it yet.

Defensively, Kepler isn’t what he once was. He’s now more of an average presence in the outfield, and his arm doesn’t offer much. He’ll be 33 on Opening Day, but if he’s available on a one-year deal, he’s the type of low-risk, medium-reward signing that could pay off if the bat rebounds even a little.

The White Sox need offense, and Kepler’s profile – especially his past power and ability to work counts – makes him an intriguing buy-low candidate.

Verdict: Target

Michael Conforto: The Name Value Doesn’t Match the Fit

Michael Conforto’s career arc has been a rollercoaster. A former first-round pick, he looked like a budding star in New York after a 33-homer season in 2019 and a .927 OPS in the shortened 2020 campaign. But since then, it’s been a tough ride.

A shoulder injury wiped out his 2022 season, and while he showed flashes of his old self with 35 homers over two years in San Francisco, 2025 was a different story. Conforto hit just .199 with a .638 OPS – the worst season of his career.

And the deeper numbers don’t offer much hope. While his plate discipline remains strong, his ability to square up the ball has fallen off a cliff.

Defensively, it’s even more concerning. He was one of the worst defensive outfielders in baseball this past season, and at 33, he looks more like a designated hitter than a viable everyday outfielder. The White Sox already have Benintendi, another left-handed bat with limited defensive value, so adding Conforto would only compound the issue.

For a team looking to upgrade its outfield – not just fill it – Conforto doesn’t move the needle in the right direction.

Verdict: Pass

Final Thoughts

The White Sox are in a transitional phase, and the outfield is one of the clearest areas in need of reinforcements. Whether it’s a platoon bat like Refsnyder, a bounce-back candidate like Kepler, or a more aggressive swing at a higher-tier free agent, the front office has work to do.

But if the goal is to add depth, versatility, and upside without breaking the bank, Refsnyder and Kepler both bring something to the table. Conforto, on the other hand, feels like a move that wouldn’t move the White Sox forward – and at this point, that’s the only direction they should be looking.