Boston Red Sox: Jon Lester is a buy-low free-agent option

The Red Sox could consider a reunion with former ace Jon Lester.

The last time that Jon Lester hit free agency he was among the most desirable talents on the market. On the heels of his best season, Lester landed a 6-year, $155 million deal with the Chicago Cubs. That contract expired when the Cubs declined his $25 million club option for 2021, sending Lester back into a market that promises to be far less fruitful in the wake of the worst season of his career. The Boston Red Sox have been kicking themselves for letting Lester go and now that his value has reached a low point, is this the time to explore a reunion?

Red Sox fans have been clamoring for Lester’s career to come full circle with a return to Boston. Lester has also indicated that he’s open to returning to where it all started for him before he hangs up his cleats. However, we have to keep in mind that Lester is no longer the ace we remember.

There’s no question that Lester lived up to his contract with the Cubs. Almost any amount would have been worthwhile considering Lester’s excellence on the postseason stage helped deliver the franchise their first World Series title in over a century but his overall production matched what they expected from him. In fact, it’s eerie how similar his results were in Chicago compared to what he accomplished in Boston.

Red Sox (nine years): .635 W%, 3.64 ERA, 1.28 WHIP 8.2 K/9, 3.1 BB/9
Cubs (six years): .635 W%, 3.64 ERA, 1.24 WHIP 8.4 K/9, 2.6 BB/9

Lester was in vintage form for the majority of his time in Chicago before fading in the end. The lefty was a below-average starter in 2019 when he went 13-10 with a 4.46 ERA and 1.49 WHIP. That first sign of decline foreshadowed a brutal end to his tenure in Chicago.

Lester was one of the worst starting pitchers in baseball this year. His career-high 5.16 ERA and career-low 6.20 K/9 both ranked fourth-worst among qualified starters.

The drastic decline in his strikeout rate correlates with a concerning dip in velocity which has been trending in the wrong direction for years. He’s never been a flame-thrower but Lester would sit 93-94 mph with his fastball at his peak. His velocity has steadily declined in recent years, falling to 90.8 mph last year and 89.8 mph this season, per FanGraphs.

Velocity certainly isn’t everything but it’s tough to get by when you’re struggling to reach 90 on the radar gun. When pitchers lose that much zip on their fastball it tends to be reflected in their production and the data supports that with Lester. His 7.2% swinging-strike rate was the worst in the majors among qualified starters and a primary reason for his sudden drop in strikeouts.

A lack of strikeouts means more contact and when hitters have no trouble catching up to his pitches it means it will be solid contact. Lester’s 38.9 Hard Hit %, 88.9 Exit Velocity and 12.3 Barrel % this year were his worst since Statcast began tracking this data in 2015.

So this suggests that Lester is washed up and the Red Sox should avoid him in free agency, right? Not if you believe David Ross. The Cubs manager joined WEEI’s Rob Bradford on the Bradfo Sho podcast to explain why he believes Lester is primed for a bounce-back year.

"“If you look back, I don’t want to give the world the scouting report on Jon, but he came into spring training and he had some velocity he hadn’t had that early really since he had been in Chicago,” said Ross. “He came in at a really good place. I think for a lot of people, especially veteran players, it was really tough to stay sharp during the quarantine time. You saw some of these guys who had great years and you saw some guys who just couldn’t get it going. I think Jon was in the middle of that. He had some highs and lows. He had some really good spurts. I know it’s in there but the velocity really never ticked back up to where I think he can get. Having an offseason and really reworking his program and downtime, I think you’re going to see a really good Jon Lester next year.”"

Ross makes a fair point about certain players struggling with the interruption to their routine due to the pandemic. The manager claims that Lester’s velocity was fine back in March but he wasn’t able to ramp it back up again during an abbreviated summer camp that followed a three-month shutdown.

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If the decline in velocity is responsible for Lester’s terrible season and that decline can be blamed on an unprecedented situation, it stands to reason that Lester will improve with a normal offseason to prepare. That’s not to suggest that the southpaw will be back in vintage form for his age-37 season but even a slight uptick in velocity should restore significant value.

It’s too much to hope for Lester to regain the 91.5 mph average fastball velocity he had in 2018 when he won 18 games with a 3.32 ERA. If he can regain an extra mph to return to the level he was at in 2019, Lester would be a viable back of the rotation starter.

With Eduardo Rodriguez and Chris Sale returning next season, Boston doesn’t necessarily need to break the bank to improve their rotation. It would be sufficient to find a starter who is either an upgrade or a cheaper version of Martin Perez, whose $6.85 million option was declined. Lester could be both if you’re bullish on him regaining some of that lost velocity.

MLB Trade Rumors predicts Lester to receive a 1-year, $5 million deal. If that prediction proves reasonably accurate, why not take a shot at buying low on Lester?

The Red Sox need to be careful not to be overly sentimental or overpay in an effort to rectify their past mistake. If the price is right though, a reunion is worth considering. Bringing back Lester would buy some goodwill with their scorned fan base. The short commitment at a salary low enough that it shouldn’t prohibit them from making other moves means there is minimal risk.

Boston might have their eyes on a bigger prize to boost their rotation and there’s room in the budget to make a splash. If they allocate those funds elsewhere and settle for a cheap starter to plug in at the back of their rotation, they could do a lot worse than Lester.