In dealing for Edward Cabrera, Cubs again choose a trade over free-agent spending

Standing 6-foot-3 with a shock of red hair and a powerful left-handed swing, Owen Caissie briefly auditioned with the Chicago Cubs last summer, hitting one home run in 26 at-bats, before being optioned back to Triple-A Iowa.

Yet, that fleeting glimpse does not capture how much Caissie symbolizes this era of North Side baseball.

The winter after their blockbuster Kyle Tucker deal, the Cubs packaged Caissie and two young prospects (shortstop Cristian Hernandez and infielder Edgardo De Leon) in a trade with the Miami Marlins for Edward Cabrera, a talented starting pitcher who brings upside and three seasons of club control.

As evidenced by Wednesday’s move, rather than spend exorbitant amounts of money on the best free agents, the Cubs are willing to mortgage their farm system in offseason trades.

With a payroll that has not kept pace with other National League powerhouses, and a data-driven, model-based framework for talent evaluations, the Cubs usually proceed with caution rather than emotion.

Given the club’s elite defense and pitching infrastructure, it would not be completely shocking if Cabrera outperformed Dylan Cease, Michael King and Tatsuya Imai, three free agents the Cubs unsuccessfully pursued this winter.

Long intrigued by his talent, the Cubs can put Cabrera on a different program and make a few slight adjustments, hoping to unleash his full potential.

These are always complicated choices, shaped in part by the parameters set by the ownership group and the business side of the organization. Jed Hoyer’s baseball operations department certainly heard the criticisms after a conservative approach to last summer’s trade deadline, when the Cubs did not acquire a top-of-the-rotation starter for the playoffs.

With four big hitters remaining as free agents — Tucker, Bo Bichette, Alex Bregman and Cody Bellinger — the offseason vibes may shift yet again by the time Cubs Convention rolls around in mid-January.

The origin story of Caissie, the young Canadian slugger and Miami’s headliner in the Cabrera trade, represents the jumping-off point.

In late 2020, faced with Theo Epstein’s abrupt exit, a high-profile group of upcoming free agents and pandemic-related budget cuts, Hoyer’s newly reconfigured front office released Kyle Schwarber and traded Yu Darvish, who remains the last pitcher the Cubs signed to a nine-figure contract, to the San Diego Padres. Caissie was one of four prospects dealt to the Cubs, along with pitcher Zach Davies.

Six seasons later, via Cabrera’s arrival, the Cubs should finally receive some major-league value from that Darvish trade, which signaled the beginning of a rebuild, even if the organization would not label it as such.

Sliding into Chicago’s 2021 rotation, Davies posted a 5.78 ERA in 32 starts for a team that collapsed before the trade deadline. The three non-Caissie prospects the Padres gave up (Reginald Preciado, Ismael Mena, Yeison Santana) have either been released or have not yet advanced past the A-ball level.

That attrition left Caissie, a well-regarded prospect who had outgrown Triple-A Iowa and should get more runway to prove himself in Miami.

Cam Smith, Chicago’s first-round pick in the 2024 draft, took advantage of a similar opportunity when he got traded to the Houston Astros in the Tucker deal. Smith made Houston’s Opening Day roster and finished with nine home runs, 51 RBI and .671 OPS in 134 games. His rookie season was worth nearly 2 bWAR; solid, but not spectacular.

In targeting Tucker as a one-and-done player, the Cubs did not engage with Juan Soto or Corbin Burnes, essentially ruling out two elite free agents at the outset of last offseason. While the second half of Tucker’s season was an injury-plagued disappointment, his fantastic start helped push the Cubs toward their first playoff appearance since 2020.

To make room for Tucker, the Cubs dumped most of Bellinger’s salary in a trade with the New York Yankees. The pitcher the Cubs received in that deal, Cody Poteet, was designated for assignment last March.

This broader strategy could someday look prescient.

History also shows that Soto’s 15-year, $765 million contract with the New York Mets could end badly. The start of Burnes’ six-year, $210 million deal was marred by Tommy John surgery for the Arizona Diamondbacks pitcher. Avoiding extremely long-term commitments and substantial deferral payments might help propel the Cubs toward another era of sustained success.

At the moment, the Cubs have only two players on guaranteed contracts that stretch beyond 2026, the final season of baseball’s collective bargaining agreement. Depending on what the next economic system looks like, going lean could put the organization in a much stronger and more nimble position for the future.

But given the big names on the free-agent market, the likely subtraction of Tucker from the lineup, and a projected luxury-tax payroll roughly $32 million beneath the first threshold ($244 million), this current snapshot of the Cubs still looks incomplete.

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