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South Side Mailbag: White Sox Upgrades to Second Base

by MillennialSox

It’s no secret that the Chicago White Sox have a glaring second-base-sized hole on their roster as it’s currently constructed. Much has been made about this concern during this offseason, including by yours truly on this site – you can check out my article here. If the White Sox are to acquire a second baseman that’s better than Leury García once the lockout ends, they are going to need to do so via trade.

Many names have been thrown out about who the Sox should acquire, but it seems to be done without the context of how the Sox should make the acquisition. It’s pretty easy to say, “Rick Hahn should go trade for Player X”. It’s a lot harder to say, “Here are the players Rick Hahn will need to give up if he is to acquire Player X.” As such, I have recruited our Michael Suareo and Brian Barry to help me out. Below are several second base options that we think could realistically be made available on the marketplace, and what we think it would take for the Sox to acquire said talent.


Phillies: Jean Segura

Phillies Acquire: Craig Kimbrel (RHP)
White Sox Acquire: Jean Segura (2B/SS)

MillennialSox: This trade makes so much sense on paper. Both players roughly will make the same amount in 2022 (Kimbrel will make $16MM while Segura will make $14.25MM. Plus, the Sox will have to pay him an additional million-dollar buyout if they don’t want to pay his 2023 salary of $17MM). The Phillies bullpen was atrocious last year, and have infielder Bryson Stott waiting in the wings. Further, current Phillies GM Dave Dombrowski previously traded for Kimbrel when he was the GM in Boston. The Sox already have an excellent back end of the bullpen and need second base help. This trade is like peanut butter and jelly. Why has this not already happened?!

Well, this trade might already be dead in the water, because according to Matt Gelb of The Athletic, the Phillies a.) seem to have a Wink Wink deal that their newly acquired bullpen assistance Corey Knebel will be the closer and b.) Dombrowski seems uninterested (probably rightfully so) in paying $26.5MM for two relief pitchers between Knebel and Kimbrel.


Mets: Jeff McNeil

Mets Acquire: Sean Burke (RHP)
White Sox Acquire: Jeff McNeil (UTL)

Brian Barry: The void at second base going into 2022 is nothing foreign for Sox fans. It seems like every Tom, Dick, and Harry has been discussed as a possible trade target for the Sox after the lockout ends. One of the more realistic options is Jeff McNeil.

You take one look at McNeil and think he’s been in the league for 10 years. However, he’s only had 368 career games and 1,450 plate appearances for the Mets, which equates to roughly 2.5 seasons. He’s amassed a solid .299/.364/.459 career slash line with a 124 OPS+. While he had a down year last year, the body of work shows that he’s a good professional hitter. Now, he doesn’t have a ton of power (37 career HRs and only 11 in his last 172 games), but the Sox’ lineup possesses plenty of that and we simply need good at-bats and sound defense from our second baseman. Additionally, he’s always hit righties well, which we Sox fans have been enamored with when it comes to off-season targets. He has a career .303 average and .850 OPS versus righties. To quote one of my favorites in Larry David, that’s “pretty, pretty, prettttttay good.”

I haven’t seen a ton of McNeil being that he’s in the National League, but I like the idea of an experienced big leaguer from the left side playing second base and hitting 9th. His poor numbers last year may give Hahn and co. the opportunity to buy low as well. At 29 years old and only earning $2.5 million this upcoming year (ARB 2 & 3 in the next two off-seasons), I would gladly welcome him via a trade.

Sean Burke is the Sox 2021 3rd round draft pick who is only 22 years old and has the fastball life and frame (6’6” 230 pounds) to develop into a nice power arm for the Mets.


Angels: David Fletcher

Angels Acquire: José Rodriguez (SS), Dallas Keuchel (LHP) + $8MM
White Sox Acquire: David Fletcher (INF)

MillennialSox: I can’t imagine the Angels are extremely eager to trade away David Flecther. He’s not a clubhouse cancer like Jeff McNeil and LA doesn’t have a Bryson Stott prospect waiting in the wings to replace Fletcher if he leaves, but if the Angels aren’t overly thrilled with David Fletcher’s production and don’t feel he can contribute going forward, it would behoove them to trade him away. Trading Flecther for Dallas Keuchel would be two teams trading away a distressed asset and hoping for rehabilitation.

The Angels would be incentivized to trade away David Fletcher since he’s coming off of a season where his OBP was under .300 and his wRC+ was 70. On its face, that’s clearly worse than what Leury García can give you. However, if you’re the White Sox, you’re hoping Fletcher can rebound to his pandemic season where he slashed .319/.376/.425, good for a wRC+ of 122. Or at minimum, he can rebound to hitting .290 with an OBP of .350 like he did in 2019. Further, Fletcher is an excellent defender. If you assume he’s going to bat 9th in the lineup and allow everyone else to score runs, the second baseman can at least play the position very well. In 2021, Fletcher was in the 95th percentile in Outs Above Average. Lastly, he’s under contract until 2025 and has club options for 2026 and 2027. He’ll make $4MM in 2022 and the most he’ll make without any club options is only $6.5MM throughout the life of his current contract.

On the flip side, the Angels get pitching – an area they’ve sorely lacked in during Mike Trout‘s tenure with the team. Dallas Keuchel is certainly no sure thing in his own right, and it’s dubious whether his acquisition after a year where his ERA was 5.28 and his FIP was 5.23 would actually bolster the Angels rotation. But White Sox would eat half of Keuchel’s salary for LA to take that risk, and the Angels would also be getting a decent prospect in José Rodriguez in return as well.

I feel confident this trade could get done, but it still feels lopsided towards the White Sox and the Angels can still just spend on free agents if they want to improve their rotation. Further, I think the Sox can also do better in terms of which second baseman to acquire.


Athletics: Tony Kemp

A’s Acquire: Gavin Sheets (OF/1B), Reynaldo López (RHP), Jonathan Stiever (RHP), Micker Adolfo (OF)
White Sox Acquire: Tony Kemp (2B/LF), Sean Manaea (LHP)

MillennialSox: Noah Phalen wrote about acquiring Tony Kemp and an A’s pitcher in his Post-Lockout Targets article for Sox On 35th, which you can check out here. That’s because the Oakland A’s seem willing to part with anything that isn’t bolted to the floor, and even then they probably would trade that away as well if you were willing to come to California and unbolt the thing yourself. One of the many holes the Sox also need to fill is a left-handed pitcher (assuming they don’t re-sign Carlos Rodon). The A’s have both a second baseman and a Southpaw in Tony Kemp and Sean Manaea, respectively. I imagine Oakland would be far more interested in parting with Elvis Andrus and his almost $7MM salary for 2022 (worse, Andrus is due $15MM in 2023 if he gets 550 PAs in 2022 or 1,100 PA combined in 2021 and 2022). His contract would be much more enticing if his OBP didn’t start with a “2” in 2021, though he would obviously come with a cheaper price tag.

Instead, the Sox should attempt to acquire Tony Kemp. 2021 was his breakout season where he slashed .279/.382/.418 in 397 PA. It would somewhat be a risk on the Sox part as Kemp will be 30 heading into 2022 and having never hit that well over the course of a full season. However, it’s a risk the Sox can absorb thanks to re-signing Leury García and also acquiring Manaea in the deal.

Oakland still sheds payroll without having to completely tear the whole thing down while the White Sox acquire pieces on team-friendly contracts (Kemp will make $2.25MM and Manaea will make $10.2MM in 2022) that bolster their 2022 roster without hurting them too bad in the short term. This move is partially contingent on the Sox signing a free agent right fielder like Michael Conforto in the off-season as well so Andrew Vaughn can DH and the Sox are free to move Sheets. Though, even without a prize right fielder offseason acquisition, this move makes too much sense for the South Siders.


Yankees: Gleyber Torres

Yankees Acquire: Craig Kimbrel (RHP), Matthew Thompson (RHP), Victor Quezada (3B)
White Sox Acquire: Gleyber Torres (2B/SS)

Michael Suareo: Gleyber Torres is a difficult player to evaluate. After the 2019 season, he appeared to be on his way to stardom with a .278 batting average and 38 home runs. He has looked like a completely different player since, though. In the COVID shortened 2020 season he only hit 3 home runs and struggled defensively. That did not improve much in 2021 either, as he posted a .259/.331/.366 slash line with only 9 home runs in 127 games. He appeared to play much better in the 2nd half of the season but still did not look like the all-star caliber shortstop the Yankees thought they had. With them rumored to be in the market for one of the available big-name free agent shortstops, Gleyber could be the odd man out. That being said, he is still only 25 and is controllable for the next three seasons, so if the Yankees do make him available for a trade, he won’t necessarily come cheap.

I know it seems like Craig Kimbrel gets thrown in many trade scenarios for the White Sox; however, it makes some sense here. Both are players that their teams have the flexibility to move on from (assuming a shortstop signing for the Yankees), and both can probably help other teams more than their own. While the Yankees still have Aroldis Chapman, he is coming off a somewhat down year and they seemed to lose some confidence in using him in save situations last season. Craig Kimbrel seems exactly like the type of trade target the Yankees would look for, although a 1 for 1 swap probably isn’t realistic. Adding a pitching prospect like Matthew Thompson and a lower-level prospect could be enough to get a deal done. Again, this is all contingent on the Yankees signing one of the free-agent shortstops.


Royals: Whit Merrifield

Royals Acquire: Andrew Vaughn (LF/1B), Dallas Keuchel (LHP)
White Sox Acquire: Whit Merrifield (2B/OF)

MillennialSox: Nothing makes White Sox fans angrier than even the mere suggestion of trading away Andrew Vaughn. Even if the idea is thrown out there and the ultimate conclusion is “No, the Sox should not trade away Vaughn”, the fact that you had the gall to even bring up the notion to trade away Andrew Vaughn makes fan’s blood boil. So here’s a trade that you’re absolutely going to love!

When I was coming up with my own off-season plan of improving the Sox while also staying under a budget of $170MM for the season, I was trying to think of realistic suggestions to get rid of the albatross that is Dallas Keuchel’s contract. He’s owed $18MM in 2022, and if he pitches 160 innings this upcoming season, his player option automatically vests and he’s owed $20MM in 2023. Needless to say, Keuchel can’t come close to pitching how he did in 2021 to make it worth it for the Pale Hose to have him pitch for them going forward.

The Kansas City Royals are one of the few teams where they can take on Keuchel’s full contract, easily release him right before Dallas hits 160 innings, and are fine no matter how good or bad he pitches because he can eat innings. The Royals also have an asset that’s useful to the Sox- their All-Star second baseman Whit Merrifield.

Even if you believe Merrifield’s first season of a wRC+ under 100 in 2021 was a trend and not a fluke (I do not), he’ll still be a massive improvement over Leury García. Merrifield is also set to make only $2.75MM in 2022 and there’s a team option for 2023 where Merrifield will be owed $6.5MM. Whit Merrifield is good and cheap, but the Royals are very bad and could and should flip him for pieces to help them in the long term. Also, Kansas City is still a super cheap franchise and is not just going to take on additional payroll of Dallas Keuchel’s contract just because they can (Unless the new CBA includes a salary floor, fingers crossed). As such, they need to have their beaks whetted. They need their palms greased. That’s where Andrew Vaughn comes in. Vaughn is good enough, young enough, and cheap enough where it makes for the Royals to not only part with Whit Merrifield, but also take on Dallas Keuchel’s full contract without the Sox having to eat any part of it.

If the White Sox are also willing to take on Andrew Benintendi and his $9.6MM owed in 2022 (which I personally wouldn’t be against), I suspect it will be a lot easier to take Whit Merrifield off of the Royals hands without giving up Andrew Vaughn. And obviously, Sox could pry Merrifield away from Kansas City without giving up Vaughn anyways. But where’s the fun in that? As Will Ferrell’s character says in Blades of Glory, “It’s provocative! It gets the people going!”


Padres: Jake Cronenworth

Padres Acquire: Andrew Vaughn (LF/1B), José Rodriguez (SS), Craig Kimbrel (RHP) + $6MM
White Sox Acquire: Jake Cronenworth (UTL)

Michael Suareo: This would be a dream acquisition for the White Sox. Jake Cronenworth checks every box they could ask for: Lefty bat, solid defense at 2B, and controllable for several years. His 4.4 fWAR and .266/.340/.460 slash line would be a welcome addition to this lineup. However, he won’t come cheap. The Padres aren’t rebuilding anymore, and Cronenworth gives them a great building block for both this season and beyond. Despite top prospect CJ Abrams knocking on the door to the big-league club, they do not HAVE to trade Cronenworth. This should lead to a premium asking price.

This offseason, there has been a lot of debate about whether or not the White Sox should trade Andrew Vaughn. My stance has always been that they should only consider it for an above-average player who is an immediate upgrade at a position of need and isn’t just a rental. Well, Cronenworth is a guy who checks those boxes. It is a steep asking price, but one that puts the Sox in a great position for both now and in the long run. The Padres have been rumored to be looking to trade Eric Hosmer to clear some salary, potentially opening up a spot for Vaughn, and are also in the market for a new closer since Melancon signed with the Diamondbacks. Well, it just so happens the White Sox have a guy in Craig Kimbrel who they can spare. The luxury tax might make this complicated, as the Padres are pushing the limit there. If the Sox are willing to eat some money here, then it would be a solid fit. Those two, plus an additional solid prospect, could be enough to pry Cronenworth away from the Padres if they are willing to part with him.


Diamondbacks: Ketel Marte

Diamondbacks Receive: Andrew Vaughn (LF/1B), Garrett Crochet (LHP), Jared Kelley (RHP)
White Sox Receive: Ketel Marte (UTL)

MillennialSox: I was having some fun with you earlier about trading away Andrew Vaughn for Whit Merrifield, but I’m being honest with you now. If the Sox truly want to have Ketel Marte as their second basemen for the foreseeable future, they will need to give up a valuable piece (or three) of their own. In 2021, Marte slashed .318/.377/.532 with 14 home runs in 90 games, good for a wRC+ of 139. In 2019, Marte slashed .329/.389/.592 with 32 home runs in 144 games, good for a wRC+ of 149. When Ketel Marte is on the field, he’s an offensive beast. Marte is also on a decent team-friendly contract as well. He’ll be owed $8MM in 2022, $10MM in 2023, and $12MM in 2024.

Arizona doesn’t have that high of an incentive to trade away their best player, but it’s also not a terrible idea either. Marte will be 28 in 2022 and 31 if the D’Backs want to re-sign him after his contract ends. The team is also awful and there’s very little hope they’ll be competitive during the remaining three years of Marte’s contract. If they want to sell now and obtain multiple prospects for the future- think about what the Sox did with Chris Sale and José Quintana in 2016 and 2017, respectively – they can get those. The Sox will be able to live without Vaughn, Crochet, and Kelley during this current Championship window they find themselves in (again, partially contingent on also a Michael Conforto-esque free agency acquisition) while Arizona is able to restock their organization with young, cheap elite talent.

Between the high price tag and Marte’s litany of injuries he suffered last year, the Sox most likely won’t go this route. But if they do, the rest of the league is put on notice.


As we hopefully trek closer towards the end of this lockout, keep your eyes peeled on social media @SoxOn35th for any and all White Sox updates!


Featured Photo: New York Mets/Twitter

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Coach Bobby V

Give me gleyber deal . It will stink around town watching madrigal on the north side but I would love to have cubs former top prospect to counter it . Plus he is a better baseball player & has a way higher ceiling so far than Nicky 2 strikes .

Keon Milsap

It’s time to start dumping these minor leaguers for big league talent. Need a 2B, outfielder, and starting pitcher.

Al Rad

The past trade is a total joke. Most are horrible at best.

jpfarr202

All this conversation about giving away the store for a second baseman ignores the obvious: the WS already have the best solution, IE Leury Garcia. Look at 2019 when he hit in front of Abreu 279 average and 93 runs scored. Bat him ninth and he will hit front of Anderson, Robert and Abreu. With all that speed, Abreu could have 150 RBI this year. Don’t tell me about defense: the Sox have had 2 gold gloves in the last three years and dumped both of them. Save Kimbrel for a team that will overpay with prospects and leave a… Read more »

Barney Miller

Tony Kemp isn’t Ryne Sandberg. That would be a considerable overpay.

John Smith

Wow a lot of bad ideas here and some awful, awful overpays. Trading Vaughn or Jose Rodriguez would be huge mistakes, although Croneworth and Marte would be excellent. The Sox outfield depth (RF especially) is not good enough to even think about trading Vaughn. Does anybody think Eloy won’t run into another wall or player again if he is in the field all the time? They should just sign a decent 2b and not trade anybody. Segura is probably not happening, but is straight up better than McNeil, Fletcher, Kemp. Fletcher and Kemp are very mediocre and would hardly be… Read more »

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