The Lovable Reunion - Jon Lester on SNAPPING at Anthony Rizzo, EPIC Cubs World Series stories, David Ross standing ovation

Three-time champ, five-time All-Star, cancer survivor, and absolute big‑game bulldog—welcome, Johnny Lester; we’re on your turf, and we’ve got stories to pull.

I’m not rich, I’m wealthy—credit Josh Beckett for that line—and yeah, the vets I came up with could scare a room into shape.

You could’ve picked anywhere in free agency; why buy into us when we were still climbing?

I expected to return to Boston after the Oakland trade, but the Cubs visit flipped it—Theo’s vision, Wrigley’s rebuild, then Joe getting hired made it real; the Giants dangled the seventh year I wanted, but Chicago felt like the place to plant roots, and I never regretted it.

I remember how heavy that choice was for you—history in Boston, kids born there, a home there—yet you still bet on a new chapter.

Fun contract twist—I woke up to MLB Network crawling 25 private jet hours across the screen and had to call my agent to learn I actually had them; best surprise perk ever.

Tell the Bub City night, because that’s how I ended up in Chicago.

At two in the morning I told Theo to sign Rossi even if the OPS said otherwise, because we needed a selfless vet who knew the job; I called him seven times, Theo negotiated by chugging from a stein to signal numbers, and we landed two years for five with a road suite ask while our agents slept.

When you and Grandpa walked in, the room changed; that first live BP in 2015 was the most intense I’ve ever seen—we all knew it was go time.

Boston teaches accountability fast—you show up in spring with cameras locked on every bullpen, so after my worst year I trained like Day One mattered, and that edge came with me to Chicago.

Boston fans later told me there’s no price too high for you—that passion is different; the Midwest loves hard too, just a different temperature.

You were my compass when I got cancer at 18—you said enjoy the good days and be a kid when you can, then I promptly fainted in the hallway and you asked for water like a pro; later I faced you and saw six pitches for two punch‑outs and decided I still loved you.

That advice is what I tell every kid—some days you can train, some days the bathroom feels like Everest—and yeah, that front‑hip cutter you saw was a fresh toy we were working on.

In 2016 you went 19 and five with a two‑oh‑two; what stat actually mattered to you?

Two hundred innings—I wanted to post, be accountable, and out‑prepare everyone; I never checked the opposing starter because I face their lineup, not their ace.

You’d go out with the boys, then be first in the weight room the next day; that standard hit harder than any speech.

Routine kept me calm—the night‑before crown and sprite, film, nap, same warm‑up, even test‑run boxers until one pair earned the job; I learned in the 2007 World Series that a locked‑in routine quiets the noise.

We drilled picks every spring; what actually happened on the mound?

It was a yip like chunking a simple chip—so I made everything else elite: holds, slide steps, varied looks, a modified quick pitch; Joe backed the plan, and we kept the run game in check.

Favorite regular‑season start that year, non‑playoffs?

Closing out a two‑one in Pittsburgh when Joe let me finish, and a scorcher in Atlanta where I ignored Rossi, refused to bury a breaker to Freddie, gave up the hit, watched his gear fly, then settled in and won anyway.

We opened 27 and nine because we were relentless—Joe preached a fast start, we embraced the target, and even our spring skits kept it loose while we hunted teams down.

I own this—I told the media we needed to clean up our pitching during a skid, and you stormed in ready to rip my head off while I was foam‑rolling; I apologized, learned the line about keeping it in‑house, and that lesson shaped how I led later.

That is culture—hold each other accountable without tossing teammates to the wolves; straight out of a winning room.

Then came Sunday Night Baseball versus Seattle—front office called up a spot starter to rest the rotation, we fell behind, rallied on a walk‑off squeeze, and Theo walked in and told the whole clubhouse the decision was on him; that ownership added fuel.

I was extra salty because it pushed my Oakland start and my Pebble Beach plan for eight guys, so I looked Theo in the eye and asked if I could still play—he said go swing it, we flew down, stayed together, hit Pebble, came back, swept, then capped the weekend with a 49ers‑Chesney night; Joe and Davey’s let‑them‑live approach made us tighter and better at work.

Last game of the season, you waved Joe out and he told me he was taking me out first; I was stunned and melting down in my mask.

I’d asked Joe that morning to give you your moment before mine if the game flowed right; he said love it, and watching you get that send‑off was worth everything.

That kind of quiet move is why we won—you did so much nobody saw.

You were different in October; what flipped?

The stakes wake me up—the flags, the flyovers, the buzz by pitch one; I do the same routine, tune out the ace across from me, and lean into the moment.

Game one against the Giants was icy and loud—you gave us eight, Javy barely snuck one into the basket, and we won one‑nothing; we even back‑picked with the bunt on because we trusted each other to make a bold play, and that fearlessness carried into the Dodgers series where Miggy’s grand slam cracked game one open.

Miggy kept the whole room on one pulse, even hobbling on a cortisone shot before that grand slam; we joked about rally beers, but it was really about keeping everyone loose—what did that stretch feel like to you?

He should’ve stuck with the heater and not left a spinner there, but either way the postseason turns everything up; you’re wired from the car to the clubhouse, and every sense is on high alert.

Walk us through how your plan shifted from a scouting-report heavy Game 1 in Cleveland to the locked-in version of you in Game 5.

I learned with you in 2013 to pound four-seamers in and build off that, not nibble; against Detroit’s mashers we went hard at the hands until they adjusted, and that mindset carried me into Game 5 where I knew I was on it.

You take NLCS MVP at Wrigley after we beat Kershaw—massive deal, huge pressure, curse talk everywhere—what did that actually mean to you?

Honestly it felt like doing my job; we’d only cleared the first bar, because the target was winning the whole thing in what became one of the wildest World Series ever.

That night at your place felt like a band rehearsal—Eddie Vedder in the backyard, guitars out—then Game 1 we tightened up and Wrigley got tense by Game 3 and 4; how did you reset for the grinder that was Game 5?

We overcooked the plan early, then went back to your strength, set the fastball in, wore the fight, and survived a gauntlet; KB’s early shot helped, and we held on while Chappy emptied the tank.

I told the staff to give the next guy a clean inning if there was any doubt; that honesty helped us get through the sixth and keep the line moving.

Game 6 we rolled, but we were begging to get Chappy out once it was in hand; going into Game 7, what did Joe tell you and how did that shape your night?

He pulled me in after Game 6 and said, Kyle for five, you bridge to Chappy; knowing I’d pitch calmed the nerves, so I could warm the right way instead of living on the phone.

I told them not to let you burn bullets sitting in the pen because you were already throwing rockets; once they called, you needed a few hot ones and go.

Then chaos: you come in mid-inning, there’s a swinging bunt, traffic, and we’re in scramble mode; what do you remember from that mess?

I rushed a throw, we collided at first, I turned my ankle and felt loopy, then a ball got by and two scored; I was sick about it, then I finally exhaled when I got one back with the homer.

I wanted that last out before Ramirez because my stuff was crisp, but we were still up; either way, the group kept its head.

Rajai’s homer—what was the call, and what were you thinking as it left?

I lived on high heat because I didn’t trust the split in that spot, and he was choked up and ready; I wore that, but credit to him, and even more to Chappy for coming back out and going clean with the weight of the world on him.

Almora’s tag to second was a winning play most people don’t make, and that set up the inning; little things flipped it.

What happened in the rain delay, because the dugout felt haunted a few minutes earlier?

It was quiet, then J-Hey spoke up and hit reset—zero-zero, let’s go—and Schwarber walked out saying he’d smoke the first cutter he saw and did; that belief spread.

I ducked up the tunnel after they staged for a celebration and saw banners and champagne ready; I chucked a cleat, they tore it all down, and I hustled back to the fight.

Where were you on the final outs and what flashed through your mind when the ball found KB?

I was pacing with Borsello, Carl got two quick ones, a walk brought in Monty, and Borsie said, trust the spin; first-pitch curve rolled to third, and I nearly launched over the rail before slamming the brakes.

We hugged on the field, I accidentally took the trophy home, and woke up to texts that you were mad at me; fair?

Sleep-deprived and salty, yeah, I asked where the trophy was and heard you had it; I cooled off fast, but in that moment I wasn’t thrilled.

Parade day was nuts; what happened with that wire?

A camera cable snapped tight across the top deck and smacked us—Lackey lost his shades, my nose was bleeding, and my wife stuffed a tampon up there so I could keep waving; it could’ve been way worse.

Before that, we toasted with a bottle dated to the early nineteen-hundreds with our dads; the history of it all hit hard.

On stage, five million strong—what did that wall of people do to you?

From the side it felt huge; at the mic it felt endless, and I blurted something unpolished because emotion just blew past my filter.

You always told us winning cleans up messes, and it did; that run changed everything.

Teams chase winners because experience under pressure travels; that’s why those clubhouse lessons matter.

You see it in how long greats keep jobs—rings and know-how carry weight; organizations want that in the room.

Looking back a decade, what would you tell younger you?

Enjoy it a bit more and put extra time into relationships; I was so locked on routine that I sometimes skipped moments—like when Kenny Chesney was strumming upstairs at Fenway before a World Series start—and I wish I’d paused for ten minutes, then gone back to work.

You changed the Cubs by how you prepared, how you loved your teammates, and how you quietly took care of people; that generosity and edge taught me how to carry myself.

If you’re my guy, you’re family, and I’ll get you home for a funeral at midnight or pick up the tab because winning together demands that kind of care; I wasn’t always sunshine, but I was all-in on us.

One memory you’d relive?

Stepping onto Wrigley’s top step for Game 5, scanning wall-to-wall fans and feeling there wasn’t an empty seat in the world; and the 2013 flyover at Fenway, when the afterburners rattled the night as I toed the rubber.

Your warm-up song hit and I was belting it while you set your breath; I was wrecked in the best way.

Ten years on, the headaches fade but the legend sticks—cheers to a run that still gives us chills.