The World Series is set to begin on Friday night in Milwaukee with the Brewers taking on the Tampa Bay Rays. It sure to be a great series of two teams who play similar styles of baseball and will both be looking for their first World Series title. Once the series has concluded, the focus for all 30 teams will shift to the offseason ahead. When speaking about the offseason last week, White Sox GM Chris Getz indicated the team could be in pursuit of outfield upgrades. Here is one addition the White Sox could make that would be a mistake, as well as one dream target and one more realistic option.
Dream Target: Randy Arozarena, Seattle Mariners
There is perhaps no better fit on the open market than Randy Arozarena for the White Sox, however, he’s possibly the best outfielder available this offseason, so the competition will be fierce. Arozarena’s production dropped off a bit after he won Rookie of the Year with the Rays in 2021, but he turned it up again following a 2024 trade to Seattle. Arozarena hit a career-high 27 home runs in 2025, and followed it up with 26 and a huge improvement in batting average and OBP in 2026, and he made the All-Star team in both years. In addition, Arozarena cut down his strikeout rate by 5% in 2026 as he started going the other way more. Now entering his age-32 season, he’ll look to cash in on back-to-back All-Star appearances with a strong multi-year deal this offseason. Whether the White Sox will actually be interested is not yet known, but with a miniscule payroll and a contending team, there’s no reason they shouldn’t at least ask how much it’ll cost. I think the odds of them winning a bidding war, however, are pretty low.
LEADOFF HOMER ➡️ WALK-OFF HOMER
— MLB (@MLB) August 23, 2026
RANDY AROZARENA WINS IT FOR THE @MARINERS! pic.twitter.com/iCYCRYwo4u
Realistic Target: Ian Happ, Chicago Cubs
A former first-round pick of the Cubs back in 2015, Ian Happ has been one of the most underrated players in baseball since his debut in 2017. In ten big league seasons with the Cubs, Happ never posted an OPS+ below 100. He won a Gold Glove in left field in every year from 2022-2025, and made the All-Star team during a 2022 season in which he posted 4.3 bWAR. Despite hitting 24 home runs, Happ didn’t have his best season in 2026– he hit just .218 and struggled mightily against lefties– but he’s been consistent enough throughout his career to believe he’ll bounce back. Happ could slot into left field for the White Sox, moving Sam Antonacci into a utility role and giving the White Sox a switch-hitter who plays good defense and brings interesting offensive upside. His down season should lead to a more reasonable contract than someone like Arozarena. I think Happ would be a very solid addition to the White Sox outfield, and his price shouldn’t be unreasonable.
Mistake: Trent Grisham, New York Yankees
After accepting the qualifying offer as a free agent last offseason, Trent Grisham will hit free agency again and look to cash in on a multi-year contract. His 2026 season was a significant step back from his 2025 campaign, though some of his underlying metrics still look strong. In 2025, Grisham launched a career-high 34 home runs and posted an OPS of .812. He bet on himself by accepting the qualifying offer, and that gamble doesn’t appear to have paid off. He hit just 18 home runs this season, albeit with 76 less at bats, and his OBP dropped from .348 to .308. Grisham also posted -5 OAA in center field this season and ended with below-average sprint speed. For the White Sox, I’m not sure how much of an upgrade he’d be, though he’s certain to get paid like it. Both Tristan Peters and Brenton Doyle posted strong defensive numbers in center field, and the duo combined for nearly as many homers as Grisham in 2026. I’d look elsewhere for outfield upgrades and avoid this one.
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