Chicago Cubs: Which ‘modern’ teammates will have their number retired?

The Chicago Cubs list of retired numbers isn’t incredibly extensive, but who could be the next player to join the list?

When a professional sports team–especially the Chicago Cubs— retires a number or jersey, it can be the highest honor bestowed on the player that wore the jersey number aside from being inducted into the respective sport’s Hall of Fame. Currently, Fergie Jenkins, Ernie Banks, Ron Santo, Ryne Sandberg, Billy Williams, and Greg Maddux all have their flags flying above the outfield fences.

Maddux is the only member on the list who did not spend the majority of his career with the Cubs. Maddux played ten years for the Cubs across two stints in the Windy City, and spent 11 seasons with the Atlanta Braves, winning the World Series in 1995. Maddux also has his number 31 retired with the Braves, the only member of the Cubs’ retired number club with his name retired by a second team.

Other Cub legends should have their number retired, but haven’t gotten the honor yet, such as Andre Dawson (8), Lee Smith (46, also worn recently by long-time Cubs pitcher Pedro Strop) and of course Sammy Sosa (21). Dawson only spent five years of his twenty-year career with the Cubs, however, and Smith spent seven full years of his career with the Cubs. Sosa and the Cubs’ relationship has been strained for years, and it may be impossible to fix it.

An argument could also be made for Kerry Wood having his number 34 retired in a few years after Jon Lester is no longer a member of the organization. Wood is most famous for his 20-strikeout game in his fifth start ever in the Major Leagues, but could never really stay healthy after that, eventually becoming a relief pitcher and even closed games for the Cubs in 2008.

Maybe the Cubs will retire 34 for both Wood and Lester, ala Jenkins and Maddux. Both players are deserving in their own way.

Chicago Cubs’ Jon Lester

As mentioned above, Lester shares his number with Kerry Wood, and Lester has developed his own legacy. He represents the start of the run the Cubs have been on since 2015. When he agreed to a six-year contract in the 2014 offseason, it meant that the Cubs were ready to compete, and have they competed. The Cubs won 90+ games four seasons in a row, made the playoffs four seasons in a row, made three straight appearances in the NLCS, and capped it off with the championship win in 2016.

The days of Lester in a Cub uniform, as well as this core, are ending in two or three years, and the  Cubs need to find a way to get back to the postseason whenever baseball resumes. Maybe a possible shortened season will help the Cubs in their quest to get back to the playoffs, who knows.

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In his five seasons with the Cubs, Lester has posted a 3.54 ERA in 159 starts, and he also won the MVP of the 2016 NLCS along with Baez. Lester also recorded his first Major League hit, extra-base hit, and a home run with the Cubs. He’s hit a home run in each of the last three years.

His best days are likely behind him, though, and he gave up his highest hit total as a Cub in 2019, but the ball was massively juiced last year, and that may have played a factor. 2020 is the final year of his contract, and there is a vesting option for 2021, which doesn’t look likely. It’s very possible that he has thrown his last pitch as a Cub, and possibly his final pitch in the Major Leagues.

Lester is a borderline Hall of Famer, and he should definitely be honored in the Cubs Walk of Fame and his number flag above the outfield walls. He deserves that much for all he’s done as a Cub. If this is it for him, all we can say is thank you.

Chicago Cubs’ Anthony Rizzo

Well, this one is about as obvious as beer and hot dogs at a baseball game. Anthony Rizzo has been everything that embodies what it means to be a Cub since 2012. He has his own charity, has won the Roberto Clemente Award for his off-field work, and on the field he has won three gold gloves, been to three All-Star games, and won three Gold Gloves. Rizzo is top ten in franchise history in home runs and has a chance to crack the top five if he finishes his career in Chicago.

He has been hit by the most pitches of any Cub in history, which is more of a painful record than anything. Rizzo is tied for tenth all-time in career OPS numbers as a Cub. He is moving up the record books and has the second-most home runs ever hit by a left-handed hitter in Cubs history. He is currently at 217 dingers as a Cub, 218 overall, and the record for left-handed batters is 392 set by Williams. Rizzo’s .376 on-base percentage is fourth among Cubs’ left-handed hitters.

Rizzo was the centerpiece behind the whole rebuild that Theo Epstein and company orchestrated. Rizzo has dealt with a lot of losing and stuck with the team to win in the end. He signed a seven-year deal to keep him as a Cub shortly after he came up to the Majors in 2012. He had a short stint with the Padres in 2011, but it was forgettable.

Cubs’ GM Jed Hoyer has had Rizzo at every stop, and one of his first order’s of business was to acquire Rizzo to the Cubs as well. He never stopped believing in Rizzo, and fans never stopped believing in this front office.

For everything Rizzo represents, from the years of losing to the culmination of a championship, to surviving cancer as a high school student, Rizzo is a great example to never give up and keep going. That’s what the Cubs did, and number 44 will always be Anthony Rizzo.