Lester likes Cubs’ chances to take another step in 2026
As usual, the Cubs did a nice job of building hype during their convention this weekend.
They had a couple big additions to introduce (Alex Bregman, Edward Cabrera), relived the historic 2016 season, brought back a couple old favorites for the first time in a while (Joe Maddon, David Ross).
One question remains open to debate: Did the Cubs get better this winter?
They essentially replaced Kyle Tucker with Bregman. Both are coming off disappointing seasons. Careerwise, Tucker's OPS of .865 is slightly better than Bregman's .846.
The Cubs are counting on Bregman bringing a well-documented commitment to winning. Maybe Bregman helped make Tucker a better player when both were in Houston.
On the pitching side, everyone is back from last year's starting rotation. Then the Cubs are adding Cabrera and expect Justin Steele to return from Tommy John surgery relatively soon. Steele said he threw off the mound Friday for the first time.
Pitching depth is important, but putting it to good use isn't easy. The Cubs can't just send anyone to Iowa until needed or preschedule stints on the injured list.
New Cubs Hall of Famer Jon Lester seems heavily invested in the success of his old team and shared his thoughts when meeting reporters Friday.
“At the end of the day, it's kind of like defense in football — starters win you championships,” Lester said. “I'm biased because I was a starter, but I think that you build your team on starting pitching, and then you win games based on the back end of your bullpen.”
Lester's theory was essentially correct last season. The Dodgers had two starters peak in the postseason — Yoshinobu Yamamoto (1.45 ERA) and Tyler Glasnow (1.69). Roki Sasaki, after barely pitching in the regular season, was nearly unhittable out of the bullpen.
On the flip side, last year's World Series was essentially a toss-up, and Toronto nearly won thanks to a dominant offense. Vladimir Guerrero Jr.'s 1.289 playoffs OPS is what the Cubs were hoping to get from Tucker. That's the kind of performance worth breaking the bank for.
The Blue Jays' next two postseason slugging standouts, Addison Barger and Ernie Clement, made less than $3 million combined. So it's also true there's no way to predict what will happen.
Do the Cubs have elite performers at any of the three main phases — starters, bullpen and offense? Well, it's possible.
Cade Horton was the best pitcher in MLB after the all-star break. Does he pick up where he left off or see a sophomore slump?
Daniel Palencia was an effective closer for much of the season. The Cubs have managed to piece together successful bullpens more often than not, but they have a trend of star relievers fading fast. Adbert Alzolay, Julian Merryweather and Porter Hodge are three names that come to mind, though Hodge will get another chance this year.
In each of the past two seasons, the guy who started as the main closer was released before the season ended, Hector Neris and Ryan Pressly.
If Horton was no fluke, Matthew Boyd builds stamina after his first full season in several years, and Steele finds his old form, then the Cubs have a chance for a strong rotation, with Cabrera sort of a wild card.
That still leaves Jameson Taillon, Shota Imanaga, Colin Rea and Javier Assad in reserve. How do the Cubs manage that list?
“I think the more you can avoid kind of terminal decisions, the better,” president of baseball operations Jed Hoyer said. “If you have a guy with options and a guy with a guaranteed contract, I think at the end of spring training it's important to preserve your optionality.”
If there are any moves left to make, it's probably adding more relief arms. The Cubs have signed Phil Maton, Hoby Milner, Hunter Harvey and Jacob Webb. Maton has the best track record of those four, but Palencia's consistency and a Hodge bounce back are what's likely to make or break the bullpen.
Modern MLB is also about slug, and the Cubs have plenty of questions in the batter's box. Michael Busch was the real breakout star in 2025, finishing 10th in OPS. At the all-star break, Seiya Suzuki ranked 17th and Pete Crow-Armstrong 23rd. After the break, Ian Happ picked it up, but Suzuki fell to 113th in OPS, while PCA was No. 131.
It feels like everyone in the Cubs lineup has a wide variance, including Moises Ballesteros, who figures to be the primary designated hitter.
“I think what Jed has done is really set up the Cubs to succeed,” Lester added. “I think they're set up for the long haul of the season. Biggest thing is get Steele back and get your pitchers right for September. That's it. And then figure it out from there.”
It's a little vague maybe, but that's the blueprint of a Cubs Hall of Famer.