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Friday, October 30, 2026Oct 30

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MLB Winter Meetings Things to Know

SAN DIEGO (AP) – Some things to know as Major League Baseball’s winter meetings head into the third day on Wednesday:

WINDY CITY WONDERS

North Side, South Side, it’s fun to be a baseball fan in Chicago this offseason. Jon Lester agreed Tuesday to a $155 million, six-year contract with the Cubs, who earlier in the day acquired All-Star catcher Miguel Montero from Arizona for a pair of minor leaguers. Lester turned down a chance to return to Boston, where he helped pitch the Red Sox to a pair of World Series titles before he was dealt to Oakland last summer. While the Cubs seek their first championship since 1908, the White Sox try for their second since 1917 and first since 2005. After agreeing with free-agent closer David Robertson on a $46 million, four-year deal late Monday, the White Sox acquired former Cubs right-hander Jeff Samardzija from the Athletics in a six-player trade on Tuesday to join a revamped roster that includes first baseman Adam LaRoche and left-hander Zach Duke.

UN-KEMP

With a crowded outfield that includes Yasiel Puig, Carl Crawford, Andre Ethier and Matt Kemp, the Dodgers have discussed a possible deal to trade Kemp down the Interstate 5 (or the Pacific Coast Highway, if a longer trip with a view is preferred) to the San Diego Padres. While the Dodgers ended the New York Yankees’ 15-year streak as baseball’s biggest spender and could afford Kemp’s huge contract, the Padres are not likely to take on all of the $107 million he is owed over the next five seasons. Through two days of the four-day session, Kemp remained in Dodgers blue.