Did Jon Lester, A Throwback Pitcher In A Modern Era, Build Himself A Bridge To The Hall Of Fame?

Perhaps Jon Lester was always destined to be the bridge between eras.

He was selected in the second round of the 2002 draft by the Red Sox, when the Sox — in the opening months of the John Henry regime and running on 84 years removed from their most recent championship — were just starting to rebuild the franchise’s farm system and reputation, which had turned barren and rotten, respectively, under the stewardship of John Harrington.

In 2005, his final full minor league season, Lester pitched for Double-A Portland and threw 148 1/3 innings, which didn’t even rank him within the top 100 amongst minor leaguers. In 2019, the last season before the pandemic, just 28 minor leaguers threw at least 148 1/3 innings.

When Lester made his major league debut in 2006, his rotation mates included a trio of of veterans — Curt Schilling, Tim Wakefield and David Wells — who each finished their careers with at least 200 victories and 3,200 innings thrown. Wells and Schilling ranked sixth and eighth in wins and sixth and ninth in innings, respectively, among active pitchers when they threw their final pitches in 2007. Wakefield last pitched in 2011, when he ranked second among active pitchers in both wins and innings pitched.

Lester was diagnosed with cancer late in the 2006 season but returned to make 12 regular season appearances (11 starts) for the Red Sox in 2007 before winning Game 4 of the World Series — which clinched the Red Sox’s second title in four years — and then throwing a no-hitter while tossing 210 1/3 innings as a 24-year-old in 2008, when he was one of nine pitchers age 24 or younger to throw at least 200 innings. It has been done just 29 times since then and once (by Shane Bieber in 2019) since 2016.

Lester won 110 games for the Red Sox, the most by any homegrown pitcher since 1983 draftee Roger Clemens, as well as a pair of World Series rings before he was traded to the Athletics at the 2014 trade deadline. (Which proved some parts of new eras are just like the ones that preceded them, and that the Henry-operated Red Sox could alienate franchise icons and make ill-advised trades as adeptly as Harrington, the Yawkeys and poor Harry Frazee)

Following the season, Lester signed with the Cubs, whom he helped to the most cathartic championship of this or any other century in 2016. As the 2021 season ended, Lester ranked third among active pitchers in both wins (200) and innings (2,740, 370 behind the lone active hurler with 3,000 innings, Zack Greinke).

The next ranking of active pitchers will not include Lester, who concluded a career defined by throwback numbers and rituals (not many big leaguers wind down from a start with a can of beer or three these days) by announcing his retirement Wednesday.

But while Lester settles into the laid-back life of a retiree, the task of figuring which side of the bridge most defines his career — and the fun of figuring out whether or not he ranks as a Hall of Famer — has just begun for the rest of us.

Neither the traditional nor modern measures are initially friendly to Lester. In addition to finishing 100 wins shy of 300, Lester ended his career with 2,488 strikeouts and a 3.66 ERA. He made five All-Star teams and finished in the top five of the Cy Young balloting three times, with a peak of second place in 2016. He led the league in a pitching triple crown category just once (an NL-high 18 wins in 2018).

Lester’s WAR of 44.2 per Baseball-Reference.com ranks 153rd all-time, below barely-hanging-on-the-current-ballot likes of Andy Pettitte, Tim Hudson and Mark Buehrle as well as a spate of one-and-done peers (Wells, Johan Santana and Roy Oswalt) and ahead of just 10 Hall of Famers — only two of whom (Jack Morris and the late Catfish Hunter) debuted after World War II.

Per JAWS — the system designed by writer, Hall of Fame historian and Hall of Fame voter Jay Jaffe that combines a player’s career WAR and the peak generated by his peak seven-year period — Lester ranks even lower at 157th all-time at 39.4. 

Yet Lester ranked seventh among active pitchers in WAR at the end of last season, behind Greinke, Clayton Kershaw, Justin Verlander and Max Scherzer, all of whom are likely or rock-solid Hall of Famers, as well as 32-year-old Chris Sale and former Cardinals teammate Adam Wainwright, the latter of whom is building an interesting 21st century Hall of Fame case.

By the time Lester debuts on the Hall of Fame ballot in 2027, the only pitcher who can be considered anything close to a lock to surpass his 200 wins is Scherzer, who enters 2022 with 190 wins. The future is uncertain for Kershaw (185 wins), who battled elbow trouble last season and is a free agent for the first time, while Wainwright (184 wins) who won more than 15 games last season for the first time since 2014 and is likely retiring at the end of 2022. Only four other pitchers have more than 130 wins, and none of the quartet of David Price (155 wins), Ervin Santana (151 wins), Johnny Cueto (135 wins) and J.A. Happ (133 wins) are likely to pitch long enough to get to 200 wins.

Likewise, Scherzer (2,536 2/3 innings) is the only active starter with a realistic shot at surpassing Lester’s 2,740 innings. Only six other pitchers have reached 2,000 innings — Santana, Kershaw, Wainwright, Price, Cueto and Madison Bumgarner, who turned 32 in August and is 706 innings behind Lester but has thrown just 636 1/3 innings the last five seasons.

Lester’s case as one of the best postseason pitchers of his generation is even sturdier. He won three World Series rings while going 9-7 with a 2.51 ERA in 26 postseason appearances (22 starts) covering 154 innings — just shy of a season’s worth of pressure-packed performances in which he pitched to an ERA more than a run lower than his regular season mark.

He was 1-1 with a 2.72 ERA in seven potential clinching or elimination games (six starts) for the Red Sox, Athletics and Cubs — an ERA inflated by the fateful 2014 AL wild card game, when Lester gave up six runs over 7 1/3 innings, including three in the eighth inning as the Royals began their stunning comeback.

In addition, Lester went 3-0 with a 1.80 ERA in three Game 5 starts — in the 2013 ALCS, 2013 World Series and 2016 NLCS — when his teams were tied at two games apiece in a best-of-seven series. All three teams closed out the series in Game 6.

Lester’s candidacy might also benefit from the sense of the moment he displayed in announcing his retirement. While Lester was in clear decline the last three years (23-19 with a 4.67 ERA and 1.48 WHIP), it would have been understandable if he felt tempted to return after going 4-0 with a 3.40 ERA in his final 10 starts last season for the Cardinals.

But Lester, who turned 38 last week, told ESPN.com Wednesday his career had “…kind of run its course” and he valued the opportunity to exit on his own terms. At some point in the 2030s or 2040s, perhaps his candid, self-aware exit will be looked back upon as the final piece to the bridge Lester — despite possessing neither the numbers of an old-fashioned throwback nor the numbers of starters asked to produce in shorter bursts — built himself to the Hall of Fame.