Dodgers Offseason Could Reshape Their Title Window In A Huge Way

Will a trio of strategic moves propel the Los Angeles Dodgers towards a World Series title by revitalizing their roster and securing key talents?

The Los Angeles Dodgers may have just been swept by the Milwaukee Brewers in the National League Championship Series, but that hasn’t shaken Vegas. They’re still the betting favorites to win the 2027 World Series, a reminder of how loaded this roster still looks on paper.

Even so, there’s work to do. The Dodgers need help in a starting rotation that has been hurt by injuries, they need to replace bullpen pieces lost to free agency, and they could use more youth in the position-player group. With that in mind, a dream offseason for Los Angeles would come down to three moves.

The biggest one starts with Tarik Skubal. The Dodgers gave up three top prospects with the hope of not losing him for nothing this offseason, but they also knew free agency was coming and that a bidding war would follow.

Los Angeles may not want to hand out another long-term deal in the $400 million range, so one possible path would be convincing Skubal to take a shorter contract with a high AAV and opt outs. However it gets done, the dream version of this winter ends with Skubal still in Dodger blue.

Then there’s the possibility of adding Elly De La Cruz. There are rumors that the Cincinnati Reds could be open to trading the superstar shortstop, who is entering his first year of arbitration eligibility.

If he’s truly available, the Dodgers would be positioned to make a serious push. They could build a package around top outfield prospects and major-league ready pitchers, and they’d likely prefer not to include top prospect Josue De Paula.

De La Cruz, who turns 25 in January, would immediately become the Dodgers’ shortstop of the present and future and give the club a young star to anchor the next wave. It would also mean Mookie Betts moving to second base, a spot that would be better for his body anyway at 34 years old.

The third piece is less splashy, but it could matter just as much: Josue De Paula taking a real step forward with his defense. The Dodgers believe he could be a generational hitter, and if he becomes an above-average defender, that could set him up as the team’s everyday left fielder next year.

Even a jump to average, or simply serviceable, would be a win. The fact that the Dodgers didn’t play him in the outfield this year shows how much work remains, and this offseason will be a key chance for him to focus on that side of his game.

The organization believes the time he spent around the big league club, watching how future Hall of Famers work, will help him carry that progress into his own play.

If those three things happened, the Dodgers’ dream offseason would be complete.

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