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.
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.
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.
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.
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.
10 Hated - Sammy Sosa
When it came to playing for the Chicago Cubs and being in front of the fans, Sammy Sosa loved Chicago. It would have been hard not to as he was the biggest celebrity in Chicago after Michael Jordan thanks to the 1998 season when he smashed 66 home runs. Sosa would make seven All Star Games as a Cub, winning the 1998 NL MVP Award in the process.
9 Loved - Kerry Wood
That player that Ryan Dempster is usually seen hanging around with is his former teammate Kerry Wood. Wood made a great impression in 1998 when he struck out 20 Houston Astros in one of his first few starts. The flamethrower quickly became a fan favorite, winning the 1998 NL Rookie of the Year Award. After years of injury problems and inconsistent play, Cubs fans still loved Wood, which caused him to want to stay in Chicago.
8 Hated - Ian Stewart
Pretty much all of the players on this list are big names in one way or another. That’s not really the case for Ian Stewart, but he certainly hated playing for the Cubs. Stewart was brought into the league with the Rockies, and he would play from 2007 to 2011 in Colorado before being brought to the Cubs before the 2012 season. That would be the only season in which Stewart played in Chicago, though.
7 Loved - Ryne Sandberg
Ryne Sandberg played his rookie season with the Philadelphia Phillies, but he would end up signing with the Cubs for the 1982 season. Sandberg would end up becoming a mainstay with the Cubs, playing through the 1994 season before retiring in 1995, only to return for two more seasons afterward. Sandberg would win the 1984 NL MVP and make 10 All-Star teams during that time, as well as collecting nine Gold Gloves.
6 Hated - LaTroy Hawkins
LaTroy Hawkins started his MLB career back in 1995 with the Minnesota Twins, and became a very good middle relief man. After becoming a free agent following the 2003 season, Hawkins signed a big deal with the Cubs worth $11 million over three years. Hawkins was supposed to be the great set-up man, but ended up with closing duties. Hawkins would blow nine saves throughout the year, and Cubs fans turned on him quick.
5 Loved - Starlin Castro
After Mark Prior was one of the highest touted prospects in baseball and before Kris Bryant, there was shortstop Starlin Castro. Castro was only 20 years old when he made his Cubs debut in 2010, and hit a home run in his first at-bat. That instant success made Cubs fans think that he was the real deal, and he was a favorite despite having ups and downs both in the field and in the batters box.
4 Hated - Milton Bradley
After not staying in the same place for more than a couple of years at a time, Milton Bradley thought he finally found a home in Chicago. After being an Expo, Indian, Dodger, Athletic, Padre and Ranger, the Cubs signed Bradley for three years and $30 million. However, he would only last for one season, playing very poorly along the way. The worst gaffe was when he threw a baseball into the stands with two outs, allowing runners to advance.
3 Loved - Ernie Banks
Of course, you can’t talk about players that loved being a Cubs without mentioning Mr. Cub himself, Ernie Banks. Banks debuted back in 1953 and played with the Cubs all the way until his final season in 1971. Over that time, Banks won a pair of MVP Awards, a Gold Glove and was named to 14 National League All Star teams. Perhaps the most beloved Cub of all-time, he didn’t disappear after his career ended.
2 Hated - Todd Hundley
The son of a former Cubs player, there were a lot of expectations for Todd Hundley to come up big in Chicago. Hundley had started with the Mets and Dodgers for the first decade of his career before signing with the Cubs prior to the 2001 season. After two seasons with the Cubs, Hundley batted just .199 with 28 home runs and 66 runs batted in, which led to a lot of quick boos in his Cubs career.
1 Loved - Ron Santo
The other late, great player that will always be associated with the Cubs is Ron Santo. Unlike Banks, Santo didn’t spend his entire playing career as a Cub as he spent the 1974 season with the White Sox, but Cubs fans usually don’t even acknowledge that. While a Cub, Santo reached nine All Star games and won five Gold Gloves. The players loved Santo, the fans loved Santo and he loved them all back, leading to his number 10 being retired.
Santo was a bigger Cubs fan than anybody out there, and it really showed in his broadcasting career. In 1990, he took over as color analyst for WGN 720 in Chicago, working primarily with Pat Hughes. Fans around Chicago that couldn’t make the game preferred the radio over television just so they could listen to the Pat and Ron Show with all of Santo’s humorous anecdotes and over-the-top reactions.
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