SAN DIEGO — The trip was a Christmas present. One airline ticket. A couple nights in a hotel. A college senior heading to baseball’s Winter Meetings in December 1999.



Nick Krall had planned the trip for nearly a year. He printed a stack of resumes on the finest paper at the career services center on the Louisiana State University campus. He placed them in a small box and stuffed them in a bag. He walked into the annual baseball job fair in a hotel in Anaheim and scanned a list of openings, nearly all entry-level gigs for minor-league teams across America.



“There were 400 jobs posted on a board with thumbtacks,” Krall said.



At baseball’s Winter Meetings, a life can change in a matter of days, or minutes. On Tuesday night, the Yankees agreed to pay free-agent pitcher Gerrit Cole $324 million across nine seasons, handing out the largest contract for a pitcher in the history of baseball and guaranteeing that a generation of Coles...