Red Sox Lose Versatile Prospect to Cubs After 7-Year Stint

It's hardly the worst heist the Chicago Cubs have pulled off at the Boston Red Sox's expense this winter, but a longtime Boston prospect is headed to compete for a spot on Chicago's organizational depth chart.

According to the official Major League Baseball transactions log, 24-year-old shortstop/utility player Karson Simas signed a minor-league deal with the Cubs on Monday.

Simas was the Red Sox's 25th-round pick out of high school in the Fresno, Calif. area in 2019. After seven years in the organization, including a pandemic, an injury that wiped out half a season, and countless reassignments, it was time to take on a new challenge.

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Simas lasted a long time as a Red Sox, but never hit

Boston Red Sox bag — Apr 29, 2021; Arlington, Texas, USA; A view of the Boston Red Sox logo and a field bag during batting practice before the game between the Texas Rangers and the Boston Red Sox at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images | Jerome Miron-Imagn Images

Simas played in 334 games in the Red Sox organization, spread out across five levels. Oddly enough, the only full-season level at which he put up what most would consider to be above-average offensive numbers was Triple-A (.761 OPS), though it was only a 30-game sample size.

The 5-foot-11, 175-pound Simas' hallmark thus far has been defensive versatility. He's played at least 30 games in the minors as a shortstop, second baseman, third baseman, left fielder, center fielder, and right fielder. He's even recorded three appearances at first base to boot.

However, with a .602 OPS (.302 on-base percentage, .300 slugging percentage) across all levels, Simas' offense was never substantial enough for the Red Sox to consider him a priority prospect. They were content to move him around from level to level when needs arose -- for example, they moved him from High-A to Triple-A and back again within the span of two weeks in 2024.

Chicago stole Alex Bregman from the Red Sox earlier this month, and that's likely to go into the history books as a much more significant free agency loss for Boston than Simas will be, even in his 99th-percentile outcome.

Plus, even without Simas, the Red Sox's list of utility players either in the majors or at Triple-A is longer than ever with spring training on the horizon.

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