1. 3B Kris Bryant 2013
Far and away the best 1st round draft pick by the Cubs in recent years, Kris Bryant was very close to not being a Cub at all. Although Bryant was considered the best position player in the class, the Cubs were picking second behind the Houston Astros. Fortunately for the Cubs, the Astros selected RHP Mark Appel, allowing Chicago to bring in one of their cornerstone pieces for years to come. Bryant was instrumental in providing stability to the Cubs' lineup with his ability to hit for contact and power, while also taking his walks and putting up high on-base numbers. Combine this with the fact Bryant can play multiple positions, has a strong throwing arm and good speed, and you have a five-tool player on your hands.
Bryant is also the only player in history to win Collegiate Player of the Year, Minor League Player of the Year, NL Rookie of the Year, and the NL MVP award in consecutive years. Unfortunately, his production dipped in his later seasons in Chicago, and he was shipped to San Fransisco at the 2021 trade deadline. At least the Cubs will be able to get top prospects Caleb Kilian and Alexander Canario in exchange for Bryant, who went on to sign a large deal with the Colorado Rockies the following offseason.