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After record Andrew Benintendi deal, what’s next for White Sox this offseason?

Vinnie Duber Avatar
December 20, 2022

Rick Hahn spent the GM meetings and Winter Meetings telling reporters how unlikely it was that the White Sox would be swimming in the deeper parts of the free-agency pool.

And then the team reportedly handed out its richest free-agent deal ever.

Granted, with the White Sox’ history of free-agent spending, the five-years and $75 million for Benintendi didn’t look too gargantuan compared to some of the other contracts awarded this winter. Aaron Judge got $360 million, after all, and a trio of shortstops – Carlos Correa, Xander Bogaerts and Trea Turner – got hundreds of million of dollars on deals soaring past 10 years in length. Justin Verlander will make more than half of Benintendi’s entire deal in 2023 alone.

But the point is that the White Sox remain somewhat unpredictable. When figuring out what comes next on the South Siders’ to-do list, it’s a guessing game, but we can still make some educated guesses.

So here’s a guess at what Hahn & Co. might still be looking to get done before Opening Day.

The White Sox need a second baseman

The team’s biggest holes heading into the winter were at second base, in the outfield and in the starting rotation. The signings of Benintendi and Mike Clevinger knocked two of those items off the list, but perhaps the most glaring positional need still remains.

Given the options on the free-agent market, this is the area where we can seemingly take Hahn at his word and expect a trade. Unless the White Sox want to shell out veteran dollars for Jean Segura to be only a moderate upgrade over the jettisoned Josh Harrison, it seems a wiser use of time to discuss potential trade candidates.

Of course, as we’ve talked about plenty, crafting a trade for an impact big leaguer seems a challenge for the White Sox, too. Let’s say they wanted to target a former MVP candidate like Brandon Lowe of the Rays or a still-promising young talent surrounded by rising infield prospects like Gleyber Torres of the Yankees, or swing even bigger for someone like Jake Cronenworth of the Padres, a two-time All Star who might have just been crowded out of the San Diego infield. Who do the White Sox send the other way?

Fans have been quick to identify Liam Hendriks as having strong trade value. Plenty are ready to send Lucas Giolito away after his disappointing 2022 season. Some have even suggested trading from the core and dangling the likes of Tim Anderson or Eloy Jiménez. But such a trade creates a significant hole elsewhere on the roster, putting the White Sox in the exact same position of having to go find someone else to ready the team for a World Series chase in 2023.

Whether Hahn acquires a lower-caliber player in a smaller trade – think the deadline deal that brought in a starting second baseman in César Hernández that only cost pitching prospect Konnor Pilkington – or waits out someone like Segura for a springtime bargain in free agency, he’s going to need to figure something out before Opening Day. As useful as the White Sox might see the likes of Leury García, Romy Gonzalez, Lenyn Sosa or Yolbert Sánchez, a team gearing up for a championship-caliber season needs a little more certainty in an everyday player. Second base was a need and remains a big one.

You can never have too much pitching

Maybe it’s those same folks who are clamoring to get Giolito off the roster, but there continue to be fan calls for starting-pitching additions this winter, even after the White Sox added Clevinger in November.

It’s far from a ridiculous point, and one of Hahn’s favorite refrains is that every team in baseball would always love to have more pitching.

Though much like the cries to spend big on a starting pitcher last winter, they ignore that the White Sox, at this point, have a full boat in the rotation. It’s not to say only five guys will make starts in 2023. That’s not how baseball works, with injuries constantly forcing teams to use their sixth, seventh, eighth, ninth and 10th starters throughout the summer.

But it’s a tough needle to thread to bring in players willing to compete for a rotation spot in the spring, potentially miss out and then spend time either pitching in the minor leagues or out of the big league bullpen, especially if there are other teams who could offer them a better chance at a seasonlong starting gig.

The White Sox have taken fliers on such guys in the past, to varying degrees of success, but it’s these kinds of deals that would seem far more likely when it comes to any further pitching additions this winter. Think the huge rewards of last spring’s minor league deal for Johnny Cueto, or the huge bust that was the minor league deal for Ervin Santana a few springs back. Vince Velasquez got a major league contract from the White Sox before last season, but only a third of his 2022 appearances were starts.

If there’s any more starting pitching to be added to the group currently consisting of Dylan Cease, Lance Lynn, Michael Kopech, Giolito, Clevinger and Davis Martin, it will be additions like those. Because certainly starting depth is important and could very well be considered a significant need for these White Sox, who don’t boast too much of it in the minor leagues.

Is right field truly finalized?

“Finalized” is perhaps not a great word to use, because even if the White Sox are sky high on Oscar Colás, who knows what the spring will bring. Colás could wow and prove the apparent decision to hand him the starting right-field job a dynamite one. Or he could stumble and force the White Sox to reconsider, without having to trot him out for Opening Day until he’s truly ready.

Given Colás’ limited but existing pro experience in Japan, he figures to be readier than most prospects with his amount of time in the minors. And the rave reviews that accompanied his import into the White Sox’ organization gave the impression of someone who would be making significant contributions at the big league level. That he’s apparently ready for the big time is not exactly a shock and something that could work out swimmingly.

But then there’s the unknown, something that’s not exactly a recipe for championship-level success. There are exceptions to the rule, of course, and the reigning World Series MVP was a rookie in 2022.

I wouldn’t expect the White Sox to go out and land an everyday right fielder with Colás already in tow, but it’s not impossible, should they find the right deal. There are supposed payroll restrictions and the already-mentioned difficulties of making a trade that seem to point toward sticking with Colás, but keep in mind that the White Sox could probably use another outfield, anyway, even as a reserve.

Beintendi, Luis Robert and Colás figure to make up the everyday group out there, and Gavin Sheets is still here as a power lefty bat off the bench – not to mention the chief insurance policy for any Colás struggles – but where’s the stereotypical “fourth outfielder” who can play a number of positions out there as well as provide a solid bat?

Adam Engel fell off after spending a couple years as the perfect fit for that role, and though Sheets can swing it, he’s not terribly versatile defensively. Maybe replacing Engel – even after the minor league deals for Victor Reyes and Billy Hamilton – is still on the to-do list.

Does Yasmani Grandal need a new backup?

Grandal wouldn’t figure to be going anywhere, not coming off a career-worst season and the amount of money he’s making in the final year of his contract (which before the Benintendi signing was the richest free-agent deal in White Sox history).

Though a start as abysmal as the offensive season he put up in 2022 could send him to the same fate as Dallas Keuchel, there’s been a lot of talk about the team’s belief in a Grandal bounce back and he’s frequently praised by the pitching staff as the catcher those arms want to work with. Given the positives the White Sox still see and the probably rock-bottom trade value he comes with, Grandal figures to be the team’s No. 1 catcher in 2023.

But what about the spot on the depth chart behind Grandal?

His health is a question mark, no doubt about it, after back-to-back injury-riddled seasons. Despite his knee injury in 2021, he still managed to be outrageously productive at the plate, a low batting average accompanied by insane on-base and power numbers. Not so in 2022, though, with knee and back issues joined by woeful offensive production and anecdotal, if not statistical, defensive troubles, as well.

Full health could render all this ancient history, of course, but while Seby Zavala was as good as he’s ever been at the major league level in 2022, would the White Sox be looking for more certainty, especially defensively, for 2023? Perhaps there’s a different backup out there that would interest Hahn & Co., and remember, it can come down to the wire, like it did with the trade for Reese McGuire last spring. A spring earlier, it seemed for a while that Jonathan Lucroy might win the backup job after signing a minor league deal.

We’ll see if something similar happens this year.

Remember the amorphous needs

The White Sox need to get better in many areas following the disappointment of 2022, and though a lot of that improvement is expected to come from the guys who just went through all that disappointment, maybe there are some specialists – regardless of position – the front office could acquire to aid in specific areas.

As mentioned, Hamilton is back on a minor league deal, and no player in recent baseball history has fit the bill of a speedster like him. Base-running, of course, is only one area in which the White Sox could use a boost. Hahn spoke at season’s end about the need to improve defensively, the need to improve in power-hitting and the need for a more balanced lineup.

Benintendi is a defensive upgrade in left field, but there’s defensive improvement needed all over the field. He’s a left-handed hitter, but is the lineup balanced enough? He doesn’t do much to help the White Sox hit more home runs, so you wonder if the addition of some sort of power bat is in the offing or the White Sox will expect (and not wrongfully) for the likes of Jiménez, Robert, Anderson, Grandal, Andrew Vaughn and Yoán Moncada to rediscover their ball-go-far ways.

Speedsters, defensive whizzes and powerful pinch-hitters rarely move the needle during a time of year when fans are looking for major splashes. But they could improve this club in areas that drastically need some improvement.

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