Editor’s note: The Cubs enter the winter hoping to build a team that can make the playoffs in back-to-back seasons for the first time since doing so four years in a row from 2015 to 2018. We look at each position on the Cubs’ roster as they aim to get back to October baseball in 2026.

Next up: Left field

Depth chartIan HappOwen CaissieKevin AlcántaraJames TriantosAnalysis

The previous “Depth chart” section could very easily have stopped after Happ at No. 1.

Because left field has been Happ’s home for nearly a half-decade now.

He has appeared in at least 144 games at the position for four straight years and has shown remarkable consistency during that stretch.

From 2022 through 2025, Happ has posted at least 3.5 WAR with an OPS of .762 or higher in each year. He has a 119 OPS+ in that span, meaning he has been 19 percent better than the average MLB hitter.

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Happ is prone to streakiness in the power department, but that has just been his MO throughout his career. At the end of the year, the numbers are always there.

He has reached the 20-homer plateau in four of the last five seasons while averaging 83 RBI and 87 runs scored over the last three years.

Happ has also won four straight Gold Glove Awards and been a steady leader in the clubhouse and behind the scenes.

What’s next?

2026 will mark Happ’s age-31 season and it’s also the final year of his contract with the Cubs. Like several other key members of the Cubs’ core, Happ is set to hit free agency a year from now.

The organization also has three young players — Caissie, Alcántara and Triantos — on the 40-man roster who can play outfield.

Caissie, 23, made his MLB debut in 2025, appearing in 12 games and posting a .568 OPS. He has mostly seen time at right field in the minors, but does have experience (100 games, 97 starts) in left.

In 226 Triple-A games over the last two seasons, Caissie has hit .281/.380/.507 (.887 OPS) with 41 homers, 57 doubles and 130 RBI. He has some swing-and-miss to his game, but also an ability to get on base and can hit for power.

[Ian Happ’s Top 10 defensive plays from 2025 Cubs season]

Alcántara, 23, has appeared in 13 MLB games over the last two seasons, though played sparingly during his time in “The Show.” He hit .266 with an .818 OPS, 17 homers and 10 stolen bases in 102 games for Triple-A Iowa in 2025.

He has spent the majority of his time in center field, with only 29 games (28 starts) spent in left. Alcántara is out of minor-league options, so the Cubs cannot send him to the minors without first passing through waivers. As such, he appears to be a lock to make the 26-man roster in 2026.

Both Caissie and Alcántara were consensus Top 100 prospects in the game heading into the 2025 season.

Triantos was just added to the Cubs’ 40-man roster Tuesday evening and has mostly spent time on the infield, with just six games and 49 innings coming in left field (all in 2025).

While there is no question who will be the Opening Day starter in left field, there is plenty of uncertainty surrounding the position long-term.

Will the Cubs work out a deal with Happ to keep him in Chicago beyond 2026? Will Jed Hoyer and Co. conjure up a trade to move any of their expiring players like Happ (who has a no-trade clause), Nico Hoerner or Seiya Suzuki? Or, will the Cubs simply give more playing time to younger assets like Caissie or Alcántara to see what they have long-term?

These are questions that have to be answered in 2026, as the Cubs have plenty of paths to take with left field in the coming year.

Bottom line

The veteran will once again anchor left field for the Cubs in 2026, but there are some long-term question marks with the position given Happ’s contract status.

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