For 108 years, the Chicago Cubs were known as the Loveable Losers. A lot of that had to do with a bevy of likeable players that, despite not seeing much success on the field, were endearing to the fans that showed up to the day games at Wrigley Field. Finally, in 2016, the Cubs broke through to win the World Series for the first time since 1908 with another series of enjoyable personalities such as Anthony Rizzo, Kris Bryant and Dexter Fowler.
However, not all of the players that have come through the Cubs organization have been all that likable, or enjoyed their time at Wrigley. Some couldn’t handle the years of losing, the way that management ran the team or the fans in the stands. Despite their ups and downs, there have been more people that loved playing with the Cubs than they did hating it, especially in the past couple of decades.
Today, we take a look at some of the players that loved their time in Chicago the most, and those that hated it more than anybody. You will notice that a lot of the players that hated it didn’t meet their expectations, while most that loved it either started or ended their careers with the Cubs. Here are eight players who loved being a Cub…and seven that hated it.
15. Loved – David Ross
David Ross wasn’t thought about much around baseball other than being a journeyman catcher. Ross had started his career with the Dodgers back in 2002, and would end up playing for the Pirates, Padres, Reds, Red Sox, Braves and then the Red Sox again. Ross developed a bond with pitcher Jon Lester along the way, and signed with the Cubs before the 2015 season as his personal catcher.
Cubs fans were hesitant at first, but the lovable Ross turned out to be a productive clubhouse veteran that the young Cubs needed to get over the hump. In 2016, Ross became a focal point of the season as the Cubs and their fans threw him a “year long retirement” party that culminated in a game seven World Series win. A win in which Ross hit a home run late in the game.
14. Hated – Carlos Silva
While he was never considered a great pitcher, Carlos Silva had some fine seasons in the MLB. Silva started out with the Phillies for a pair of seasons before joining the Twins for four years and Mariners for two. During that time, Silva posted a 60-64 record, and signed with the Cubs before the 2010 season. It started off promising as Silva posted a 10-6 record with a 4.22 ERA, but things went downhill fast.
Silva’s record doesn’t reflect his 8-0 start, though he was expected to be a starter for the 2011 season. After getting shelled in a preseason game, Silva got into it while in the dugout with third baseman Aramis Ramirez. Since Ramirez had a lot of success with the team and was more valuable, Silva was shown the door and he never pitched in another Major League game afterward.
13. Loved – Mark Grace
The first player that we chose that loved playing for the Cubs was David Ross, who actually hit his first career home run off of Mark Grace. At the time, Grace was playing for the Diamondbacks, but he will always be remembered as a Cubs great at first base. Grace played with the Cubs for more than a decade, taking in a lot of day games and hitting double after double in front of the Bleacher Bums.
Grace loved hanging around Chicago and talking with Cubs fans, especially ones that were female and a little on the heavier side when his hitting wasn’t so hot. Grace remains one of the most popular Cubs of all-time for those that grew up in the 1990’s, the same decade that Grace landed more hits than any other MLB player.
12. Hated – Aroldis Chapman
Aroldis Chapman is perhaps the fastest throwing pitcher in baseball history on a consistent basis, and he played for several seasons with the Cincinnati reds for the beginning of this career. Of course, the Reds are division rivals, and Chapman didn’t always see eye to eye with many of the Cubs players. However, the Cubs would risk some assets to acquire him for their 2016 playoff run.
Chapman was never really fully accepted by the fans due to his past as a Red and also off-the-field. Even the person that plays the music at Wrigley Field was booted for playing “Smack My B**** Up” during Chapman’s warm-up. Chapman felt that he was misused during the 2016 MLB Postseason by Joe Maddon, and didn’t really entertain offers from the team. He loved playing for the Yankees and signed with New York for the 2017 season.
11. Loved – Ryan Dempster
Ryan Dempster started out his career with the Florida (now Miami) Marlins back in 1998 after the team had won their first World Series. He then departed the year before they won their next one to join the Reds for a pair of seasons. In 2004, Dempster became a big free agent signing for the Cubs, and he would remain with the team until the middle parts of the 2012 season.
Despite being shipped to Texas (in a deal that brought the Cubs Kyle Hendricks), he has remained loyal to the Cubs front office. He retired after the regular season in October 2014 and became an assistant to Jed Hoyer and Theo Epstein. If you look closely enough, you can see Dempster hanging out in the crowd at Wrigley Field or at big road games, usually palling around with another player on the list.