The Chicago Cubs traded their top prospect for a starting pitcher with three years of team control.
That means, according to longtime MLB insider Ken Rosenthal, it’s time for Chicago to go all-in to win a championship.
Rosenthal urged the Cubs to sign one of the four top outfield bats in free agency, Kyle Tucker, Cody Bellinger, Alex Bregman or Bo Bichette after they traded outfielder Owen Caissie as part of the deal with the Miami Marlins for starter Edward Cabrera.
The Cubs have ties to all four players. Tucker was a member of the Cubs in 2025, Bellinger played for them in 2024 and both Bregman and Bichette have been approached by Chicago this offseason.
Ken Rosenthal: The Cubs Need Another Big Bat For 2026
The Cubs have seemed to be out on Tucker since their season ended in Game 5 of the National League Division Series against the rival Milwaukee Brewers. Yet, Rosenthal explained why owner Tom Ricketts should sneak back into contention — especially with only three clubs offering lukewarm interest in the five-tool outfielder.
“Offensively, then, the Cubs are playing from behind,” Rosenthal wrote in The Athletic. “They have spent more than $30 million on five free-agent relievers and brought first baseman Tyler Austin back from Japan for $1.25 million. They paid the expected steep price for Cabrera, an oft-injured talent who is under club control for three more seasons. But with their trade of Caissie, they created more lineup uncertainty for their future.”
Rosenthal is alluding to the fact Caissie was the Cubs’ No. 1 prospect, who received his proverbial cup of coffee with the Cubs in September. But with him gone to Miami, and Seiya Suzuki and Ian Happ entering the final years of their contracts, there are holes to potentially fill in the Cubs outfield.
“If Ian Happ and/or Seiya Suzuki departed in free agency,” Rosenthal wrote, “an opening likely will exist for the left-handed Tucker or Bellinger, just as it did for the left-handed Caissie – and might for another talented Cubs outfield prospect, the right-handed Kevin Alcántara.”
Bo Bichette or Alex Bregman Is A Better Fit For The Cubs
There is at least one outfield hole to fill for Chicago, but it also has infield holes that may be looming as well.
Nico Hoerner, who led the Cubs in bWAR at second base (6.2) and finished second in the NL in batting average (.297), is about to join Happ and Suzuki by hitting free agency after this season. If all three left, that would be 55 homers departing from 2025.
So that’s why Rosenthal indicated Bregman or Bichette, right-handed-hitting infielders, seem to make more sense for Chicago.
“Bregman, who turns 32 in March, is the oldest of the Big Four, but some in the industry believe he might age the best and almost everyone is enamored with his leadership,” Rosenthal wrote. “Bichette, four years younger, also could play third base, forcing Matt Shaw into a super-utility role as long as the Cubs kept second baseman Nico Hoerner — which, if they are serious about contending, they absolutely should do.”
Rosenthal closed the column by challenging Ricketts, who he noted has fielded a top-10 Opening Day payroll just once since 2020.
“Without any further moves, Chicago’s first NL Central title in a full season since 2017 should be within reach, … but for heaven’s sake, the Cubs should be aiming higher,” Rosenthal wrote. “Enough with the mid-market mindset. Chicago, by population, is the nation’s third-largest city. Let’s see the Cubs act like it.”
Insider Urges Cubs To Go All-In After Edward Cabrera Acquisition