Why Jon Lester reached out about Justin Steele before he became the Cubs’ new ace

CHICAGO — Jon Lester was hanging out during a family beach vacation in South Carolina last year when he happened to turn on a Chicago Cubs game. Though the trade deadline was two months away, it had already become clear that the Cubs would become sellers and use the rest of that rebuilding season for player development. Watching the young left-handed pitcher on the Wrigley Field mound that night reminded Lester of Lester.

By the time Cubs manager David Ross checked his phone after the game, he had already received multiple text messages from Lester, his close friend, former teammate and one of the best pitchers in franchise history. Lester noticed how the Milwaukee Brewers reacted to Justin Steele’s pitches, considered the sequencing and passed along a few suggestions.

It’s not fair to compare one spectacular Cy Young Award-caliber season to a possible Hall of Fame career built over 16 years. It’s not accurate to assign all the credit to a retired dude on the couch and diminish all the hard work it took to get to this point. But this thread helps explain how the Cubs arrived as a bona fide playoff contender. Even though they’ve rarely interacted over the years, the Lester-Steele connection is real.

Lester’s main point to Ross — his personal catcher on two World Series-winning teams — centered around the idea of Steele establishing the four-seam fastball down and in against right-handed hitters on the inner third of home plate. Commanding that quadrant could help open up everything else for Steele, who had repeatedly shown flashes of potential but still needed to make that jump to become a viable major-league starter.

Jon Lester and David Ross meet during Game 5 of the 2016 World Series. (Jonathan Daniel / Getty Images)

The box score shows that Steele received a no-decision during that 8-7 win over the Brewers on May 31, 2022. Steele used up 102 pitches in five innings, allowing three runs and finishing with six strikeouts against four walks. Watching on TV, Lester focused on Steele, who was called up during the pandemic-shortened season but did not get into a game in 2020, which was the final guaranteed year of Lester’s landmark $155 million contract with the Cubs.

“There are some similarities there with how I used to pitch and how he goes about it with his four-seam and whichever breaking ball he decides to use,” Lester said in a phone conversation. “When he’s really on, that slider is pretty tight. He can use it as a putaway and a strike. But in that game, he was up a lot with his four-seam, which he did get a lot of swing-and-misses at. That’s how it seems to play. It’s got that good life and that good ride. But everybody was just kind of spitting at his slider — and he was throwing a good one that day — so I just kind of honed in on it. By the time he was done, I had already texted Rossy.”

Again, this is just one piece of the puzzle with Steele, who had the talent and athleticism to command a $1 million signing bonus out of high school as a fifth-round pick in the 2014 draft. Steele successfully made the recovery from Tommy John surgery as a minor-league pitcher. Steele eagerly took advantage of the individualized instruction at the South Bend, Ind., alternate training site in 2020. Then he quickly made an impression as a left-handed reliever on the 2021 team that was dismantled at the trade deadline.

You have to start somewhere. Lester certainly wasn’t a finished product when he made his major-league debut with the Boston Red Sox in the middle of the 2006 season. You also have to adapt, a skill Lester sharpened while performing at Fenway Park and competing in the American League East. As Ross knew firsthand, Lester’s game didn’t revolve entirely around pure stuff. It was really about understanding strengths, recognizing weaknesses and competing in the moment. Those are the same pillars that eventually made Steele an All-Star.

“I was kind of like: ‘Hey, man, I don’t want to step on anybody’s toes. I just happened to watch a game. This is what I saw,’” Lester said. “The big thing for me in that game — and this is what I ended up talking to Rossy about — is you can’t get away with the high heater. The high heater plays. You just can’t stay up there consistently and get guys to swing at his slider. His slider is a swing-and-miss pitch, and guys were just taking it like they knew it was coming. We just talked about kind of getting him back down in the zone and up by design. And then that slider should get a lot of swings because it’s got the same plane as his heater.”

Ross and Lester fleshed out the concept during a follow-up conversation over the phone. Ross then met with Steele in the manager’s office and presented Lester’s feedback. In his next start, Steele tied his career high by throwing seven innings, allowing two runs (one earned) in a no-decision against the St. Louis Cardinals on ESPN’s “Sunday Night Baseball.”

“To be honest with you, I’m glad it worked,” Lester said with a laugh. “I don’t like to do that stuff. That’s why they have pitching coaches and people like that. But I always liked to hear from guys that I played with — or even played against from time to time — and see what their thoughts were on things. Sometimes you can get a different view on it.”

Lester probably wouldn’t have shared his insights about Steele with any other manager in the game, but Ross is an exception because they earned World Series rings together as part of the 2016 Cubs and 2013 Red Sox. Lester also respects the chain of command and the tireless effort that a coaching staff puts into a 162-game season. Lester’s long history with Cubs pitching coach Tommy Hottovy also factored into it when he hit send on those text messages to Ross.

“Obviously, that whole relationship helps,” Lester said. “Even with Tommy — and as good of a relationship as I have with him — if it was a different manager I don’t think I would’ve texted. I know Rossy well enough to where if it’s warranted, he’s going to look at it and go, ‘OK.’ If it’s not, he’s going to tell me to go s— in my hat.

“I know where I stand. There’s no hard feelings, right? I knew, too, that going to Rossy and saying that wouldn’t offend Tommy, either. That’s the other part. You don’t want people that have jobs to think that Rossy’s soliciting outside sources when he has people they’re paying to do a certain job. It’s kind of a perfect storm with Tommy and Rossy being there.”

All these different forces have come together to make Steele the obvious choice to be the Game 1 starter in a potential playoff series. That’s what these past two days against the Arizona Diamondbacks have felt like, Zac Gallen getting the shutout in Friday’s 1-0 game and Saturday’s crowd of 40,391 roaring for Steele in another pitchers’ duel at Wrigley Field.

The Cubs won’t overreact to a 3-2 loss in 10 innings because Steele showed no signs of slowing down and this group has been so resilient throughout the season. The Cubs played music in the clubhouse after their third straight loss to the Diamondbacks, another team in the wild-card chase, trusting their process and believing that their luck will soon even out again.

Steele allowed one run and zero walks in seven innings against Arizona, lowering his season ERA to 2.49 across 27 starts. Steele has 16 wins this year and one loss in his past 16 starts, continually keeping his team in the game, showing the kind of competitiveness that made Lester so revered. There’s also no sense that the rest of the league has figured out Steele’s fastball-slider mix.

“He kind of has two heaters,” Lester said. “The slider works off that. When you’re down in the zone and you’re throwing strikes, guys have to guess. And then if you’re able to locate both sides of the plate, now they really have to guess. And when he can plane that ball up, now you’re messing with guys’ eye levels, not only from side to side but up and down. Even though it’s two pitches, it’s obviously very, very effective because he’s able to change their eye levels in so many different ways.”

That makes it uncomfortable in the batter’s box, especially for right-handed hitters, when Steele can buzz the inside part of the plate with velocity to speed up swings and then drop sliders underneath. The ability to navigate a lineup, create weak contact and handle the pressure is what separated Lester as one of the best big-game pitchers of his generation. Lester wouldn’t have picked up the phone if he didn’t think Steele was the real deal.

“In the big leagues, too, people talk about how you only have two pitches,” Lester said. “Well, you know, this is the horse that got you here, so let’s ride it as long as we can. We’ll keep working on things, but let’s make sure that I’m really good with these two. And then when I need it, I’ll start sprinkling in some other things. The little bit that I have been able to watch has been fun. You can see him maturing and growing and learning as he’s going.”

(Photo of Justin Steele: David Banks / USA Today)

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