If the Cubs retire #34, is it to honor Jon Lester, Kerry Wood or both?

Since the news of Jon Lester’s retirement broke early this week, there have been countless Cubs Twitter polls posing the following question in various forms: “Will the team retire #34 for Jon Lester and Kerry Wood, similar to how #31 is retired for Fergie Jenkins and Greg Maddux?”

We won’t know for some time if the Cubs will unveil a white flag with a blue ’34’ emblazoned on it down the line at Wrigley Field. But even if it happens, the organization faces a tough choice when it comes to whether they honor solely Lester or Wood gets the same level of recognition in the end.

Lester, who will make for one of the more interesting Hall of Fame discussions in five years’ time, left an indelible mark on the franchise. He accumulated 13.2 WAR during his half decade-plus (remember, his sixth and final year with the Cubs was the truncated 2020 campaign) and was a workhorse, averaging just under 188 innings per season from 2015 to 2019.

Upon his arrival on the North Side, expectations changed and he helped mold an incredibly young team into a powerhouse that made a surprising run that ended in the NLCS – only to return in 2016 as a National League Cy Young finalist, leading the Cubs to their first World Series title in more than a century.

That ring is a key differentiator between the two pitchers. We know how close Wood came in 2003 before it all fell apart – but you can also make the case Lester had a much stronger, deeper supporting cast during his time with the team, as well.

Jon Lester, Kerry Wood had very similar Chicago Cubs careers

Looking at Wood’s five-year run from 2000 to 2004 and Lester’s stint from 2015 to 2019, the numbers are eerily similar – with Lester edging out Kid K in ERA, innings pitched, WHIP and ERA+. Wood gets the nod in WAR (18.5 to 13.4) and, of course, K/9 (10.0 to 8.6).

During that span, the Texas-born right-hander made a total of four postseason starts – all coming in that 2003 season – pitching brilliantly in the NLDS against Atlanta and really struggling in the League Championship Series against the Marlins. Meanwhile, Lester’s postseason resume will go down as arguably his biggest ‘plus’ when the BBWAA considers his Cooperstown candidacy.

He brought home NLCS co-honors with Javier Baez in the 2016 NLCS, and, despite the team losing on a chilly night at home in the 2018 NL Wild Card Game, Lester was brilliant.

The numbers of these two hurlers is much closer than you think. Even so, it’s worth asking if either warrant having their number retired. Remember, every single player whose number is flapping in the breeze on a foul pole at Wrigley is a Hall of Famer. Wood’s career, while it has some unforgettable moments, namely his 20-strikeout game as a rookie in 1998, gets him nowhere close. Even Lester is a borderline candidate at this point.

With similar resumes – outside of that ever-present World Series ring for Lester – the two share surprisingly comparable Cubs careers. Do both deserve to see their number 34 retired? Neither? Only Lester? This is a debate that could go on for years and years.