Spring Training Is Here – And These 3 Cubs Could Be Gone by the All-Star Break

The sun is shining in Mesa, and the sound of gloves popping at Sloan Park can only mean one thing: spring training is officially underway. For the Cubs, that means the start of a new era under manager Craig Counsell – and with it, a lot of roster questions. As pitchers and catchers report and position players trickle in, the front office is already evaluating who fits into the long-term picture – and who might not make it to the All-Star break in a Cubs uniform.

Let’s take a closer look at three players who enter camp with uncertain futures in Chicago.

Dylan Carlson: A Make-or-Break Spring

Dylan Carlson was once a cornerstone of the Cardinals’ future. Now, he’s a 27-year-old outfielder trying to prove he still belongs in the big leagues.

Carlson’s career has been a mix of flashes and frustration – mostly due to injuries that have derailed any real momentum. Despite nearly 2,000 plate appearances in the majors, he’s posted a modest career slash line of .233/.312/.372. His 2025 season with the Orioles didn’t help his case either, as he put up a 74 wRC+ and struggled to find consistency at the plate.

Still, the Cubs see something. He’s a switch-hitter with raw power and defensive versatility, and during early workouts in Mesa, he’s turned heads with a lively bat in batting practice. The tools are still there – the question is whether the production will follow.

Carlson’s path to sticking with the big-league club may hinge on how the Cubs handle top outfield prospect Kevin Alcántara. With an option year in hand, the team could choose to keep Alcántara in Triple-A a bit longer to refine his approach, especially his swing-and-miss tendencies. That would give Carlson a window to prove he can be a reliable fourth outfielder.

But that runway won’t be long. If Alcántara starts raking in Iowa and Carlson can’t capitalize on his opportunity, the Cubs won’t hesitate to make a change.

Hoby Milner: Veteran Southpaw on a Short Leash

The Cubs have a recent track record of squeezing value out of veteran left-handed relievers – just look at what Drew Pomeranz and Caleb Thielbar brought to the table last season. Now, 35-year-old Hoby Milner is the latest to get a shot, signing a one-year, $3.75 million deal this offseason.

Milner is expected to slot in alongside Thielbar as the team’s primary lefty options out of the bullpen. He’s a soft-tosser, relying more on deception and movement than velocity, which puts a lot of pressure on command and sequencing. That’s a tightrope act – and one that gets even riskier with a flamethrower like Luke Little waiting in the wings.

Little, still just 25, brings a completely different look – upper-90s heat from the left side – and he’s hungry to reclaim his spot in the ‘pen. If Milner falters early, the Cubs may not wait long to pivot. With only a one-year deal on the books, Milner’s leash is short, and the bullpen competition is real.

Javier Assad: Caught in the Numbers Game

Javier Assad has been a jack-of-all-trades for the Cubs – a swingman who can eat innings in long relief or step into a spot start when needed. That versatility has kept him on the roster in recent years, but heading into 2026, his role is anything but secure.

Right now, Assad is penciled in as the final bullpen arm. But that spot could be in jeopardy depending on how the rotation shakes out. With Justin Steele still working his way back and Colin Rea looming as a potential sixth starter, the Cubs may not need Assad in a hybrid role for long.

Add to that the presence of Ben Brown and top prospect Jaxon Wiggins – both of whom are pushing hard for big-league opportunities – and Assad suddenly finds himself in a crowded field. If he doesn’t come out sharp in the early months, the Cubs could look to upgrade or reallocate innings to younger arms with more upside.

The Bottom Line

Spring training is about opportunity – and for Carlson, Milner, and Assad, it’s also about urgency. All three are fighting for roles on a Cubs team that has postseason aspirations and a deepening talent pool. With prospects knocking on the door and veterans on short-term deals, the roster churn could come quickly.

By the time the All-Star break rolls around, don’t be surprised if at least one – if not all – of these names are no longer part of the equation.