It’s time for the White Sox to confront their second-hardest decision this offseason. After picking up Luis Robert Jr.‘s $20 million option, Chicago must decide which Rule 5 draft-eligible players it wants to protect from being poached at the Winter Meetings.

The Sox currently have five open spots on their 40-man roster, but not all five will go to up-and-coming prospects. One opening should be set aside for a first baseman, as there are no first basemen in the minors who are expected to be ready to debut at the beginning of 2026, and Tim Elko will spend most of the season rehabbing his knee. The pitching staff’s youth could be a concern, too, so reserving another space for an experienced starter or reliever would be wise.

Teams who select players via the Rule 5 draft must keep them on the major league roster all season, or otherwise sell them back to their original team at half-price. Thus the Rule 5 draft isn’t normally a robust or aggressive session; the White Sox keeping two Rule 5 pitchers as they did in 2025 (Shane Smith and Mike Vasil) is nearly unheard of.

With that in mind, here are the three minor-leaguers the Sox should protect from the Rule 5 draft.

Tanner McDougal, RHSP
McDougal isn’t expected to be ready for The Show until 2027, but keeping him in the organization is a must. Despite having a rogh 2024, McDougal broke out in 2025. He posted a 3.26 and struck out 136 batters in 113 1/3 innings in High-A and Double-A. He also significantly improved his WHIP and batting average allowed while halving home runs allowed. McDougal’s rapid development this season justifies his 40-man roster spot.

At this stage in their rebuild, the Sox need to stockpile young arms. Keeping their No. 7 prospect should be a no-brainer.

Drake Logan, OF
Logan is a depth piece the Sox need to retain. Chicago would benefit from his strong arm and steady defense in the outfield. His bat is also a showstopper considering his rapid ascent through the minors. Logan slashed .278/.353/.397 in Rookie, High-A, and Triple-A in 2025. While his K% (35.34%) is still a major area for improvement, he offers range, consistency and defense that the Sox can’t afford to let go.

Stashing Logan on the 40-man roster is a worthwhile insurance move. While his productivity may dip as he reaches his next development phase, keeping Logan far outweighs losing him.

Shane Murphy, LHSP
Murphy’s under-the-radar season in 2025 should be rewarded with a 40-man roster spot. He managed to hold a 1.66 cumulative ERA and 0.89 WHIP in 135 1/3 innings. Murphy struck out 104, held hitters to a sub-.200 batting average, and managed to restrict opponents to four earned runs in his three starts in Charlotte, which isn’t easy. Equipped with plenty of momentum and a pitching arsenal that doesn’t let too many out of the park, Murphy is worth keeping in the system.

After going through eight different starters last season, the Sox need to pad their rotation depth. That rotation will certainly be a wild card given how inexperienced and young the group is, so having Murphy ready to jump in when ready will be essential.