SouthSideDruther’s Measured Approach


Objectives: (1) improve outfield defense; (2) balance lineup handedness; and (3) re-establish that the contention window is wide open through 2025. 


  • Lucas Giolito: $10.8M
  • Dylan Cease: $5.3M – tender
  • Reynaldo López; $3.3M – tender
  • Adam Engel: $2.3M – non-tender
  • Michael Kopech: $2.2M – tender
  • Kyle Crick: $1.5M – non-tender
  • José Ruiz: $1M – non-tender.  Ruiz, and his relatively affordable $1M projected salary for 2023, isn’t the problem.  But he represents a larger White Sox tendency towards self-sabotage by relying on known quantities instead of striving for improvements at the margins.
  • Danny Mendick: $1M – tender

Giolito is the only close call. I think he is worth a 1-year, $10.8M deal so he gets tendered.  Engel is probably better than what he showed this season and is a decent 4th outfielder option if his defense rebounds a bit, but the money that would go to him is being used to “super solve” the corner outfield spots.  See below.


  • Tim Anderson: $12.5M ($1M buyout) – pick up
  • Josh Harrison: $5.625M ($1.5M buyout) – decline.  Harrison was largely as advertised (solid defense and reasonably productive, albeit streaky, at the plate plus a good clubhouse presence).  But the rest of the roster is pretty much set and this is one of the few spots where it is relatively painless to plug in a new player.


  • AJ Pollock: $13M ($5 million buyout) — EXERCISED. I do not see a better offer out there for Pollock, especially not one from a club that has a reasonable chance of contending in 2023.  This money is as good as spent.


Try to retain, extend qualifying offer, or let go?

  • José Abreu (Made $18M in 2021) – let go
  • Johnny Cueto ($4.2M)
  • Vince Velasquez ($3M) – let go
  • Elvis Andrus ($14.25M) – let go


The Estate of Loretta Micele.  “La Russa’s Lounge” replaced “Loretta’s Lounge”, so this feels like the only fitting solution.


No. 1: Michael Conforto (four years, $92,000,000). A new White Sox free agency record!


  • High OBP lefty bat.
  • Probably does not own a first base glove, which automatically makes him a defensive upgrade over Vaughn and Sheets.
  • Injury cost him all of 2022 season and thus makes him White Sox budget compatible.
  • No qualifying offer.

Sure, Conforto hasn’t played since 2021 and his power numbers may be trending in the wrong direction.  But he has all-star upside and seems tailor-made for addressing some of the current deficiencies plaguing the White Sox.

Maybe the Sox can borrow from the approach from the Hendriks contract and make the last year a club option that if declined would allow the Sox to pay $23M in $1M increments over a 23-year period.  Worst case scenario, this would lead to a situation somewhat akin to the Bobby Bonilla Day the Mets have every year.

No. 2: Wade Miley (one year, $5,500,000 plus a club option for one year, $8,000,000 with a $1,500,000 buyout).  The Sox could do a lot worse than Miley for the back end of their rotation.  He provides a much-needed lefty starting pitcher option.  The contract is essentially a one year, $7.5M deal but with $1.5 deferred.


No. 1: Trade Lucas Giolito, Jake Burger, and Matthew Thompson to Baltimore for Anthony Santander.

Santander is a huge upgrade in RF.  Per Baseball Reference, he put up a 2.1 WAR season in 22022 with an OPS+ of 117 and 33 HRs.  Santander is a switch hitter (nice) with 2 arb years left and will be 28 years old as of opening day 2023.  He fits the Sox window and budget.  The OBP (.318 in 2022, .300 career) and batting average (.240 in 2022 and .245 career) if you’re into that sort of thing are not ideal. But on balance, Santander brings a lot to the table.

Baltimore gets a one-year test run with Giolito.  If he can recapture his 2019 magic, he’s a #1 -1.5 starter and qualifying offer candidate after the season (with a possible extension depending on many factors including how much Baltimore’s ownership is willing to spend).  If he craters, the Orioles can move on after this season. The most likely outcome is that Giolito lands somewhere in the middle as a #3 starter-type, but even that holds value on a young team looking to build on last year’s success in a crowded AL East.  I think this move allows the Orioles to chase a bigger rotation upgrade in free agency to lead the pitching staff while adding quality innings and upside. Burger (MLB ready bat with intriguing RH power but a worrying injury history and defensive limitations) and Thompson (athletic starting pitching prospect to dream on) add some value here and help balance out Giolito’s associated risks.

Giolito’s variance in performance makes it hard to gauge his value, which is already limited by his impending free agency after the 2023 season.

No. 2: Trade Oscar Colas, Garret Crochet and Gavin Sheets to Miami for Pablo Lopez and Sixto Sanchez.

BOOM. This is a very high-risk high reward trade and exactly the type of move that would shake things up for the Sox.

There’s a lot to like about Pablo Lopez.  In the past three years, he posted an ERA+ of 126, 138(!) and 108, and a FIP of 3.09, 3.29, and 3.71 over that same span.  He set a career high for innings last year with 180 and will be just 27 years old on opening day 2023 and won’t be eligible for free agency until after the 2024 season.

Sanchez is an extremely intriguing second piece in the trade as a former top prospect that has faced injuries of late, which caused some of the bloom to come off the rose.  Still, Sanchez will be just 24 as of opening day and has a #2 starter ceiling.

Colas is the driving force of this trade for Miami.  He’s a high ceiling prospect that can handle CF, an area of need for the Marlins, though his long-term home is likely RF.   The power and throwing arm are undeniable and his MLB service clock hasn’t started yet.  Losing Colas is hard, but he hasn’t reached the majors yet so his loss is more theoretical.  If Colas hits 80%+ of his anticipated ceiling, the Sox probably “lose” this trade.  But this trade is more about re-aligning talent so that the contending window is firmly set at 2023-2025, with some contracts coming off the books after the 2023 season such that the Sox have some firepower to add/adjust after this season.

Crochet is also a very intriguing piece with top of the charts stuff, though his value is dependent on (i) how well he recovers from TJS and avoids future injuries; and (ii) whether he can be successfully transitioned into the starting rotation. The Sox have had success with unorthodox deliveries in the past, but the window is now.  Crochet may be limited to the bullpen only in 2023 (admittedly he would be a late inning weapon), and thus moving him may be the best move for the current window.

Sheets is more of a throw-in, though Miami is in need of a first baseman and Sheets does offer impressive left-handed power.  I admit that part of my reason for including Sheets is to prevent the manager from trying to platoon him with Vaughn or play Sheets in the outfield.

No. 3: Trade AJ Pollock and Jason Bilous to Texas for Brad Miller.  This trade is a swap of once productive players in the twilight of their respective careers, with mildly intriguing bullpen arm thrown in. In 2022, Pollock (0.6 WAR, 91 OPS+ per Baseball Reference) offered more value than Miller (-1.6 WAR, 69 OPS+).  The gap in production is offset by the difference in salaries for 2023 ($13M vs. $4M), which would result in a net savings of $9M for the Reinsdorfs White Sox. Bilous may not be enticing enough for the Rangers to make the deal, but the idea here is basically “selling” a mid-level prospect or two to get $8M off the books.

Pollock gives the Rangers a solid outfield upgrade on a one-year commitment, which will give some time for their top OF prospects to get more seasoning. The $13M salary is an overpay, but probably not an egregious one – especially when you “offset” the $4M that would otherwise be earmarked for Miller.  The Rangers have shown a strong willingness to spend and would thus likely find Pollock more palatable from a budgetary standpoint.  Bochy and Pollock also overlapped in the NL West, so there’s that.

Miller bats lefty and his 2022 production was hampered by injury (81 games played, 58 starts) so he has some upside to bounce back to his 2019-2021 form (OPS+ of 136, 122, and 107).  But the major draw for the Sox is the $9M in savings and freeing up RF.


I think the payroll ended up in the neighborhood of the $190M budget.  I trust Hahn to defer enough money in club option buyouts to make the numbers work.  Here’s what I ended up with.


  1. Anderson (R) – SS
  2. Conforto (L) – LF
  3. Eloy (R) – DH
  4. Santander (S) – RF
  5. Robert (R) – CF
  6. Moncada (S) – 3B
  7. Vaughn (R) – 1B
  8. Grandal (S) – C
  9. Mendick (R) – 2B


Zavala (R) – C

Leury (S) – INF/COF

Gonzalez (R) – INF

Miller (L) – 1B/3B (possible DFA candidate)

Talk about balance! Conforto adds a dose of OBP in the #2 spot.  Santander injects another power threat in the middle of the lineup.  With this lineup, there is less pressure on Vaughn to immediately be a 30 HR, 100 RBI prime Abreu replacement.  Second base is mostly an afterthought.  I am envisioning an open competition/mix and match between Mendick, Romy, Leury, and Lenyn. Mendick looked excellent covering for TA last season before his own injury, so I’ll give him the nod for now.  As an aside, it would be hilarious if Leury became a full-time player post-TLR.

Seby likely gets a fair amount of playing time at catcher to try to keep Grandal’s lower half healthy.  If Grandal has another subpar season, Seby becomes much more important but the lineup has more lefty bats that would allow the Sox to bench Grandal as needed and not worry about being exploited by right-handed pitching.  Anything Miller can provide is gravy, though I fear he may be Vaughn-Playing-Center-Field level bad defensively at this point in his career.


  1. Cease (R)
  2. Lynn (R)
  3. Pablo Lopez (R)
  4. Kopech (R)
  5. Miley (L)

The biggest change here is swapping Giolito out for Lopez, who seems to have a higher floor and greater consistency than Giolito at this juncture.  Lopez’s extra year of team control means the Sox aren’t faced with losing two-fifths of their starting rotation at the end of the 2023 season. Miley is mostly just an attempt to add variety to the conversation of veteran lefty back-end starters which will likely center around Q.  I think Cueto has both priced himself out of the budget I have left, and I worry that regression and/or injury lurks.

Arm Barn:

CL – Hendriks (R)

RP2 – Graveman (R)

RP3 – Lopez (R)

RP4 – Kelly (R)

RP5 – Bummer (L)

RP6 – Lambert (R)

RP7 – Diekman (L)

RP8 – Foster (R)

The arm barn is largely untouched.  Crochet is a loss, but it is mostly theoretically since he missed last season.  Healthy and productive seasons from Bummer and Kelly would allow the bullpen to reach the upper echelons, but that would be offset other injuries, slumps, etc.  Bullpens are fickle.

The biggest upgrade from a pitching standpoint should be improved defense, particularly at the outfield corners.  A rising tide should lift all ships here.  The rotation still suffers from a lack of depth in the rotation, but that seems to be a problem that is fairly common across baseball.  Plus, Davis Martin showed flashes and hopefully can step into the #5 slot and/or serve as the swing man and first starter up in case of any issues.

It seems the 2022 White Sox planned to paper over any defense pitching depth issues by bludgeoning other teams with offensive firepower.  This roster probably follows the same plan, but hopefully with better execution via a more balanced lineup with different types of hitters (and an approach that does not prioritize singles).

In giving up two higher upside young players (Crochet and Colas) the Sox add players that fit the current core and its competitive timeline.  I held onto Montgomery but mainly because I didn’t find a deal I liked.  I would be open to moving him at the deadline for a necessary upgrade (maybe starting pitching or to fill a void created by injury).   If T.A. walks after this season, it probably means the Sox underperformed again and are headed for a rebuild anyway.  Rick Hahn’s “waves of talent” idea is a worthwhile goal, but the Sox are firmly in their window and they owe it to this iteration of their core to go for it.  Perhaps the Sox are not in place to sell out for 2023 only—especially given the months-long funeral march that was the 2022 season—but firmly establishing window from 2023-25 is needed and makes sense.

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Santander won’t cost that much.