Chicago White Sox shortstop Colson Montgomery had one of the most interesting seasons in MLB history during 2026. Once a borderline All-Star candidate, Montgomery largely disappointed in his first full year.

In 153 games, Montgomery hit 31 home runs with 87 runs driven in. By those stats alone, most people would think he had an excellent season. However, that simply wasn't the case. Montgomery struck out 227 times, breaking an MLB single-season record, and slashed a poor .197/.282/.403 for a .685 OPS. This was a stark contrast to his previous season, where Montgomery had an .840 OPS with 21 home runs in 71 games.

So, the performance begs an important questions ...

Should We Be Worried About Colson Montgomery?

Colson Montgomery had a very odd season. The left-hander hit better against lefties (.778 OPS) than righties (.644 OPS). He also hit better away from Rate Field than at home. In the first half of the season, Montgomery slashed .220/.302/.469 with 23 home runs. He seemed destined to hit 40 home runs. However, he batted a mere .163 after the All-Star break with eight home runs and 106 strikeouts in 62 games.

By the end of the regular season, Montgomery was hitting near the bottom of the order. His strikeout and whiff rates were astronomical, at 35.6 and 37.4, respectively. His xBA, squared-up rate, whiff rate, and strikeout rate were all in the first percentile (aka at or near the bottom of the league) according to Baseball Savant. It all led to Will Venable batting Montgomery ninth in the order come playoff time.

Montgomery would often chase pitches out of the zone, seemingly striking out on every fastball above the zone or breaking pitch away. With two strikes, he batted just .111 with a .426 OPS. After the All-Star break, it was fair to call it a nightmarish season for Montgomery.

So, should the White Sox be concerned? Absolutely, but there is some hope for the young shortstop. Montgomery actually had a solid postseason with the White Sox. While he struck out 11 times in 26 plate appearances, Montgomery showed signs of breaking out of his funk with a .238/.385/.429 slash line with a home run and a double, while laying off some of the pitches that did him in during the regular season.

In addition, while the young shortstop's bat was struggling, his glove didn't take much of a hit, with a +12 Outs Above Average. White Sox director of hitting Ryan Fuller has worked miracles on Montgomery before. Can he do it again?

None of this is to say that Montgomery should be traded following his first full season. After all, the entire team struggled with strikeouts down the stretch, especially against the Cleveland Guardians in the postseason.

However, it feels safe to say that 2027 will be a make-or-break season for Montgomery. The 2026 No. 1 overall pick, Roch Cholowsky, is waiting in the wings, along with several other solid infield prospects. If Montgomery doesn't have a steep improvement in production at the plate, expect the noise to grow much louder around his future with Chicago.