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MLB: Winter Meetings
Ho ho ho, might Santa Boras make a stop in Chicago?
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Don’t Cross Scott Boras Clients Off of Your Holiday List

The search to improve with at least one major signing means the White Sox could be knocking on the door of the superagent.

Baseball superagent and apparent pun practitioner Scott Boras is no longer the grim reaper over at 35th and Shields. Considered the organization’s boogeyman for years, the veteran negotiator and wordsmith just wants to get his clients their just due ... and a little more.

Some of that coin could be coming from Jerry Reinsdorf’s ownership group with the Chicago White Sox this offseason.

The White Sox currently have a projected payroll of more than $160 million for the 2022 season, but it’s the expectation of many in the industry that the club should have at least one significant free agent expenditure on the way this winter.

Could the addition ultimately come from the Boras Corporation? There are many players to choose from, if so. Corey Seager is the biggest fish on the position player side, but isn’t a likely target of Rick Hahn and company. Kris Bryant would be a welcomed addition for much of White Sox Twitter, but the 29-year-old seems destined for the West Coast. Nicholas Castellanos, Michael Conforto, Max Scherzer and Marcus Semien should be realistic targets of the club, and substantive conversations regarding southpaw Carlos Rodón have likely occurred as well.

Dealing with Boras clients regularly isn’t something that the White Sox front office is known for. They don’t often participate in the charade, bidding money against mystery teams in perpetuity as contract discussions drag on into the new year. Boras is the best in the business, though, and the White Sox are in a championship window, looking to add talent. There are experienced negotiators on both sides — and deals have been worked out before.

Rodón was drafted by the White Sox back in 2014, and the relationship with the southpaw was preserved this past season despite the club’s reluctance to extend a qualifying offer earlier this month. Blake Rutherford wasn’t drafted by the White Sox, but is noteworthy as another client of Boras Corporation. In 2019, after the unfortunate end to South Side pursuit of Zack Wheeler, the Pale Hose pivoted and landed Dallas Keuchel on a creative contract.

Contracts with Boras have been struck, and there’s no reason to believe that a perfect union can’t be consummated again.

The White Sox are right in the middle of a competition cycle, with a 77-year-old manager handpicked by the owner and a general manager who has assured everyone that the front office is operating under the premise of “business as usual” with resources available at his disposal. The club had the best pitching staff in baseball in 2021, but there is a need for at least one more starting pitcher and multiple relievers. The trade market could be the chosen path, but there are free agent options for the franchise to ingest.

Once again, right field is a significant need for the team as well. The front office has patched the hole in recent years instead of committing to a long-term option. Andrew Vaughn and Gavin Sheets could end up as internal solutions, along with Adam Engel, but if defense is a priority, outside help is needed.

And the internal options at second base aren’t even as appealing, with the leading candidates being Danny Mendick and pop-up prospect Romy González. Hahn alluded to the fact that outside help at the keystone would likely be necessary.

“We’re going to survey that market, trade or free agent, and see if there is a way to get better,” Hahn said. “We haven’t closed the door on perhaps bringing back César [Hernández] at some point. Leury [García] got some starts down the stretch, he’s a free agent and we continue to have contact with and we’ll see what the next couple weeks or months hold.”

The offense was a strength in 2021. The club finished fourth in baseball with a 109 wRC+, despite its propensity for ground balls. Power is a priority, and players who can handle right-handed pitching will be a focus for the pro scouts.

Hahn and the front office likely have divergent paths that can be taken this offseason. They could spend significant dollars on the outfield, and make a deal for an infielder. The inverse could take effect as well, or they could splurge on a big-money pitcher in a more expensive way than they’ve done in the past.

USA Today baseball insider Bob Nightengale’s predictions have become a punch line due to his willingness to be loud wrong on multiple occasions. His quotes should be taken as gospel when referencing the Chicago White Sox, however. He nails information regarding the club, and is often the chosen media conduit for the purpose of releasing public information.

Forget about Justin Verlander, as the 39-year-old former Cy Young winner has re-signed with the Houston Astros. Somehow, the seat at the table jokes are still en vogue for a fanbase that loves to dredge up old feelings on the regular. The most noteworthy piece of information in Nightengale’s tweet, however, is the indication that the White Sox will be aggressive this winter. Money will in fact be spent. It’s the allocation that we should be debating.

Verlander and Noah Syndergaard both received large average annual values on short-term pacts with their clubs. Max Scherzer is likely looking for a similar deal, approaching $30 million per season on a multi-year arrangement. The 37-year-old posted a 2.46 ERA with a 3.24 FIP while averaging 11.84 K/9 accumulating 5.4 fWAR over the course of 180 innings with Washington and Los Angeles.

Mad Max would be the single biggest difference-maker that the White Sox could add this winter. Tony La Russa is said to favor this direction, and slotting a true No. 1 starter into this rotation would greatly improve what is already a strength. Scherzer has Midwest ties, and is said to be prioritizing a contender when considering his next contract. Mad Max is a long shot, and would far exceed the club’s spending proclivities, but it’s definitely something that has been discussed in the offices at Guaranteed Rate Field.

The return of Marcus Semien has been a hot topic among the fans and within the media this week. The 31-year-old is coming off a season in Toronto where he posted a 131 wRC+ and hit 45 homers, accumulating 6.6 fWAR playing primarily second base. The 6´0´´, 195-pounder is looking to cash in for the first time this offseason, and the White Sox are very familiar with him. They drafted him twice, developed him in their system — and then traded him. He’s a different player now, though, and he’d be the bi- ticket addition that would excite the stakeholders this winter.

Semien doesn’t get on base a ton and he doesn’t hit left-handed, but he checks lots of boxes. He won’t be as expensive as the other premium infielders on the market, so the reported interest is worth monitoring. Semien is likely at the top of one of Hahn’s divergent paths. The White Sox like to strike early, and the former sixth-rounder wants to sign prior to December 1 according to ESPN’s Jeff Passan.

With room in the budget for one big ticket item, Semien should be a realistic option for the White Sox. The other path ends with finally allocating real resources to right field in free agency. Conforto would be a solid fit in Chicago, and Castellanos would put smiles on the faces of many as well.

Castellanos posted a 140 wRC+ with 34 homers in 2021 with the Cincinnati Reds. The 29-year-old hits right-handed and has little defensive value. He’d be a great addition to the White Sox lineup, but would be a precarious fit on a roster loaded with corner players destined for designated hitter.

Conforto is likely cheaper and possesses more overall upside going forward. He’s a solid defender, gets on base, and hits for power. Tim Ryder analyzed the fit for us last week and the 28-year-old definitely makes sense as a primary target. Conforto was a first round selection out of Oregon State back in 2014 and despite some struggles in 2021, he has posted a career 136 wRC+ against righties.

While of late the franchise has acted more like the big-market club it is categorized as, there very likely isn’t room in the budget for major free agents both at second base and right field. If a guy like Semien is prioritized and secured, an outfield addition could come via trade with pitching an option as well. The presence of Conforto on the roster leaves a hole at second base that could be filled in a trade, with players like Joey Wendle of Tampa Bay, Ryan McMahon of Colorado and Cavan Biggio of Toronto potentially expendable.

The White Sox need to add pitching this offseason. Hahn has noted the ability to spend and upgrade on the infield and in the outfield. Backup catcher is a priority as well.

The budget will allow for one major expenditure, as the club looks to push for another playoff appearance. Boras could provide the solution that the White Sox are seeking. Which path the front office decides to take, possibly in advance of December 1, will determine the rest of the offseason.

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