The Dodgers’ billion-dollar spree: secrets, rumors and Brad Paisley’s Pappy Van Winkle

Brad Paisley stood at his door as the cars arrived, holding a glass of his most expensive bourbon, Pappy Van Winkle 23, in each hand.

One for Los Angeles Dodgers manager Dave Roberts. One for president of baseball operations Andrew Friedman.

“I have a feeling you guys need these tonight,” the country-music star said.

Paisley, an avid Dodgers fan, had invited a group of team officials to a barn at his 100-acre farm in Nashville. The barn houses a recording studio, a kitchen, bedrooms and a bar. Oh, what a bar.

On that night in early December, Paisley’s intention was to give Dodgers people a place to unwind away from the hustle and bustle of baseball’s Winter Meetings in Nashville. Earlier that day, Roberts told reporters the team had met with prized free agent Shohei Ohtani. Roberts’ seemingly innocent revelation created a stir. Or, as Paisley put it, “DEFCON 1.”

In mid-November, ESPN reported, “If visits between Ohtani and a team are reported publicly, it will be held against the team.” Ohtani’s agent, Nez Balelo, later pushed back on that report, saying he never warned teams that directly. But every club involved in the bidding knew of Ohtani’s desire to keep the process confidential.

Friedman did not know if Roberts’ remarks would negatively impact the Dodgers’ efforts to sign Ohtani. But he could not rule out the possibility. Later that day, he spoke with Roberts. Both men remain unwilling to divulge much of that conversation. Roberts still bristles that his disclosure became an issue at all.

“I was Captain Obvious,” Roberts said. “And it just blew up into something that I couldn’t believe.”

Paisley, a self-described baseball nut who hosted the draft lottery at the Winter Meetings, was well-aware of the budding controversy. As he prepared for the arrival of his guests at around 7 p.m., not knowing Friedman and Roberts had spoken, Paisley wanted to break the tension. Pappy Van Winkle, he figured, would do the trick.

“You have no idea how much I need this right now,” Paisley recalled Roberts telling him.

The scene at the doorstep was just one of many eventful turns during the Dodgers’ wild, $1.4 billion offseason.

The gathering at Paisley’s barn turned into a rollicking affair featuring wine, whiskey and cigars — plus officials from the Tampa Bay Rays, who showed up to accelerate talks leading to one of the Dodgers’ big offseason moves, their addition of pitcher Tyler Glasnow.

The Dodgers, of course, wound up signing Ohtani, but only after a frenetic day in which reports of him potentially joining the Toronto Blue Jays surfaced, causing Roberts to unravel during a round of golf he was playing with actor Brian Baumgartner, best known for his work as Kevin Malone in “The Office.”

And the Dodgers’ whirlwind of a winter continued with their intense courtship of Japanese free-agent right-hander Yoshinobu Yamamoto, whom a number of teams lavished with gifts, exquisite meals and $300 million offers before he ultimately landed the richest contract for a pitcher in baseball history.

Interviews with more than two dozen major-league executives, players, and managers, as well as a Grammy Award-winning singer and Emmy Award-winning actor, unveiled the drama — and zaniness — behind the Dodgers’ international spending spree.

 As the world learned on Dec. 9, Roberts’ supposed misstep turned out to be much ado about nothing. Ohtani announced on his Instagram account he had chosen the Dodgers. Balelo, his agent, revealed the terms — 10 years, $700 million. Two days later, The Athletic reported that the deal included unprecedented deferrals, $68 million of Ohtani’s $70 million per year.  (At the time, no one was aware of the issues with Ohtani’s interpreter and illegal gambling that would make headlines months later. Ohtani said Monday that he has never bet on baseball or other sports and accused his interpreter of both stealing from him and lying to him, though questions remain unanswered.)

Dodgers players and staffers who had been kept in the dark throughout the team’s recruitment of Ohtani vividly recall where they were upon learning of his signing, a franchise- and industry-altering moment.

Roberts was attending a celebration of life in Manhattan Beach, Calif. His son, Cole, a minor leaguer with the Arizona Diamondbacks, showed him the Ohtani news on his phone. “I was at the beach,” Roberts said. “And I almost wanted to jump right into the ocean.”

Mookie Betts was walking down a fairway at his home course, the Lakeside Golf Club in Burbank, Calif., when someone from another fairway shouted, “Congratulations!” Baffled, Betts checked his phone and saw Ohtani’s announcement.

How did the rest of his round go?

“Not very good,” Betts said. “My phone started blowing up like I had signed.”

Second baseman Gavin Lux, napping when the news broke, said, “that was probably the best way I could have woken up.” Third baseman Max Muncy was putting his 7-month-old son, Wyatt, down for a nap when his wife, Kellie, informed him he had a new teammate.

“I’m shocked at that point,” Muncy said. “Then she told me what the contract was and I was even more shocked.”

The Ohtani deal was the centerpiece of an offseason in which the Dodgers signed nine free agents, made six trades and awarded two contract extensions. Muncy was the team’s first investment, agreeing to a two-year, $24 million extension on Nov. 2. His contract amounted to less than 2 percent of the Dodgers’ offseason outlay.

“I’d like to say me taking my nice little deal gave Andrew a lot of wiggle room to toss out a billion dollars,” Muncy said.

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Freddie Freeman was home in Orange County last October when his phone rang. About a week had passed since the Dodgers suffered their shocking elimination by the Arizona Diamondbacks in the Division Series. Friedman was on the line, wanting both to review the season and preview the offseason, as he does with a number of players.

“What’s the plan?” Freeman asked.

Friedman laid out Plan A: Sign both Ohtani and Yamamoto.

“Is Mark going to go for that?” Freeman asked, referring to Dodgers owner Mark Walter.

“We want to win,” Friedman replied. “Mark wants to win really bad.”

An offseason plan, though, rarely proceeds smoothly. And on Dec. 8, with Ohtani reportedly flying to Toronto, presumably to sign with the Blue Jays, the Dodgers’ dream scenario appeared on the verge of collapse.

Roberts was playing golf at the Rancho Santa Fe Golf Club as part of a foursome with Baumgartner, a golfing buddy. Ohtani’s decision reportedly was imminent. Baumgartner joked with Roberts that he wanted to be the first to hear the news.

Then the reports about the Blue Jays surfaced. Roberts grew distracted. His game fell apart.

“I’m usually off my phone. But then my phone is just blowing up non-stop,” Roberts said. “I literally couldn’t even get the ball off the tee. It was, like, miserable.”

Baumgartner recalled specifically that on the 14th hole, Roberts’ game “blew up,” one thing after another going wrong.

As the group got to 15, no one said a word to Roberts, observing a respectful silence.

“I’m sort of pleading with Brian the whole day, going, ‘Dude, I promise I’m not that bad,’” Roberts recalled. “And then we get to 15 and I bomb a drive like 340 because I just said, screw it.”

One of the other members of the foursome remarked, “There was a little bit of red-ass in that one, Dave.” After the group reached the fairway, Roberts explained why he was such a mess. Ohtani, he said, was apparently signing with the Blue Jays.

Friedman was alarmed by the level of specificity in the reports. He called Balelo and asked flat-out: “Has Ohtani agreed to a deal with Toronto?” Balelo said no. But Friedman did not entirely trust that answer. He knew Ohtani wanted to announce the signing himself on Instagram. Balelo, in effect, was sworn to secrecy. If the Dodgers were indeed out, the agent couldn’t let Friedman know.

The Blue Jays, though, never were convinced they were getting Ohtani.

“L.A. just made so much sense that it was hard to believe how seriously he seemed to be considering us,” team president Mark Shapiro said. “But each time the doubt crept in, there was some signal that we were legitimately in the hunt.”

One of those signals occurred in the middle of the Winter Meetings, when Ohtani flew from California to meet with Jays officials at the team’s spring-training complex in Dunedin, Fla.  Ohtani left the complex with bags of Jays gear and wearing a Jays cap — and with his now-famous dog, Dekopin, outfitted in a Canada jacket.

“My optimism peaked,” Shapiro said.

Little did Shapiro know, Ohtani took his nameplate and a cap from his meeting with the San Francisco Giants, according to a source who was present. He also took a photograph at Dodger Stadium of a locker the team set up with his jersey. Friedman thought, “That has to be some kind of sign?”

As it turned out, Ohtani was just collecting keepsakes. But his meeting with the Dodgers, which included a six-year-old video of Kobe Bryant imploring him to join the team during the team’s 2017 recruitment of Ohtani from Japan, indeed proved a success.

The Dodgers took great pains to ensure Ohtani’s presence at the stadium went unnoticed, even shutting down the team store for a period. Hours before Ohtani’s visit, club officials hosted reporters in a conference room at the stadium, discussing their plans for the upcoming Winter Meetings. Only later did the media learn Ohtani was in the building the same day.

At one point as Ohtani stood at the dugout railing, taking in the view of the 56,000-seat stadium, Friedman noticed people in the top deck. He grew concerned, thinking someone might spot Ohtani and reveal the visit. No one did.

The Winter Meetings took place the following week. The frenzy over Ohtani built to a fever pitch.

On Dec. 9, the day after Ohtani’s fictitious flight to Toronto, Friedman and his wife, Robin, were in Anaheim, Ohtani’s old stomping grounds, to watch their 11-year-old son, Zach, play soccer. Friedman was walking out to the field, talking on his phone about another potential transaction, when Balelo called with the news:

You got him. Shohei’s a Dodger.

Balelo told Friedman to inform his Dodgers colleagues that the deal was done, and Ohtani’s announcement was only minutes away. Friedman said his son’s team won the soccer game — impressive memory considering that Balelo’s call left him “blown away.”

Plan A was intact. The fun was just beginning.

“Are we done?” Freeman asked Friedman.

“No, we are not,” Friedman replied.

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The night Friedman was hanging with Paisley, enjoying the festivities inside the singer’s barn, his phone started buzzing.

The Rays’ Erik Neander was calling.

“Brad,” Friedman said, “I need you to answer this and tell the Rays’ GM that we need Tyler Glasnow.’”

Paisley, eager to help his favorite team, was happy to oblige.

“Ok, let’s make a deal,” Neander replied, playing along. “Who is this?”

“Brad Paisley,” Paisley said, before handing the phone back to Friedman.

Confused, Neander told his former boss with the Rays, “That sounded like an AI-generated Brad Paisley voice.”

“It is Brad Paisley!” Friedman responded. “Come on over.”

With that, the Rays joined the party.

“Brad really wanted Glas,” Neander said. “I’m like, I’m leaning into this. We had some drinks. Let’s go.”

Paisley admires Glasnow’s talent and considers the 6-foot-8, 225-pound right-hander “a beast.” He gave Neander an earful, teasing the Rays’ president of baseball operations from the moment he walked in the door.

“You see this top shelf, this really high-priced whiskey up here?” Paisley said. “That’s the Tyler Glasnow shelf. That’s the ‘deal’s done’ shelf.”

The deal did not get done that night, but both Friedman and Neander acknowledged it gained momentum during the gathering, which lasted until around 4 a.m. Paisley marveled at the discussions swirling around him. They were pretty much like he always pictured them, baseball people sitting at a bar and scrawling names onto napkins. But the Glasnow trade turned out to be anything but simple.

The Chicago Cubs and Atlanta Braves were also interested in Glasnow, according to team sources briefed on the discussions. So were other clubs. Glasnow, under contract for $25 million in 2024, lacked a no-trade clause, but was not without leverage. He effectively could rule out certain teams by telling Neander he would only stay with them for one season before entering free agency.

“I definitely gave him some hints,” Glasnow said.

Neander did not want to make a trade contingent on Glasnow getting an extension, viewing the extra layer of negotiation as too great a risk. Glasnow, 30, underwent a hybrid Tommy John/internal brace procedure in August 2021. He missed almost two months at the start of last season with a strained left oblique. Though he finished the year without further disruption, if the acquiring team found a problem in his physical, the deal might collapse.

Friedman, though, made it clear they would not part with the package Neander wanted, right-hander Ryan Pepiot and outfielder Jonny DeLuca, unless the Dodgers could sign Glasnow long-term. As part of the deal, Friedman also was willing to take on $8 million of outfielder Manuel Margot’s $12 million obligation. Which meant, in their $1.4 billion offseason, the Dodgers managed to collect $4 million from the Rays, one of the game’s lowest-revenue franchises.

The Cubs remained in the Glasnow talks until the end, but were not willing to make a comparable offer. Neither was any other club. So, with the Dodgers and Rays in agreement on the terms of the trade, Friedman’s next task was to reach agreement on an extension with Glasnow in a 72-hour negotiating window.

Again, Glasnow had leverage.

More than two years removed from elbow surgery, he was poised for a big season entering free agency. His agent, Joel Wolfe of the Wasserman Media Group, gave him a sense of how the market might develop.

The Dodgers were enticing to Glasnow. Friedman was assembling a powerhouse. Ohtani sent Glasnow a video, saying, “I want to hit some home runs for you.” And Glasnow was excited by the idea of returning to his native southern California and playing for his hometown team. He agreed to a four-year, $111.5 million extension with the Dodgers, on top of the $25 million he will receive this season. The deal gave him everything he wanted. Market value. The opportunity to join a World Series contender. And the chance to go home.

The trust in the relationships between Neander, Glasnow, Friedman and Wolfe helped make the deal possible. The party at Paisley’s barn served as a catalyst, tickling the music star to no end. “It’s like a joke,” Paisley said. “Country singer has two GMs to his bar.”

“He definitely gets the assist,” Friedman said.

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On a picture-perfect day in southern California, in early December, New York Yankees general manager Brian Cashman saw only clouds.

Cashman, eating lunch with Yankees manager Aaron Boone and pitching coach Matt Blake at a rooftop restaurant in the Waldorf Astoria Beverly Hills, recalls thinking, “This is what we have to compete with. This weather.”

But not just that.

Yamamoto, 25, grew up a Dodgers fan. He spent a chunk of the offseason in Los Angeles, training at UCLA. And the Yankees were not the only ones alarmed that he was making himself at home in the Dodgers’ backyard.

“He was hanging out in L.A. at the exact right time to be hanging out in L.A,” Mets GM David Stearns said. “There was a little bit of a home-field advantage.”

Yamamoto, like Glasnow, was represented by Wolfe. Within a week, he visited three cities — San Francisco, Los Angeles and New York. His meetings with the Yankees, Phillies and Red Sox took place in the Hollywood Hills, at the luxurious home of Casey Wasserman, chairperson of the Wasserman Media Group. Stearns and Mets owner Steve Cohen already had visited Yamamoto in Japan, dining with the pitcher and members of his family at a restaurant in Osaka the week before the Winter Meetings.

Yamamoto’s second go-round with the Mets was a dinner at Cohen’s estate in Greenwich, Conn., where the billionaire keeps hundreds of millions of dollars of artwork.  Wolfe jokingly equated the estate to what might result if the Louvre and British Museum had a baby.

The next day, the Yankees had their second meeting with Yamamoto. Cashman again was concerned. “It was a dark, cold, rainy weekend in New York City,” he said. “It was in the back of my mind: ‘Ah, the weather.’”

Taking no chances, the Yankees hosted Yamamoto not at Yankee Stadium, but at a swanky Manhattan hotel. That way, the pitcher and his entourage would not get caught sitting in traffic or over-exposed to the elements. The Yankees reserved Yamamoto a suite that recently had been used by Taylor Swift, Wolfe said. They also rented a restaurant in the hotel, and enlisted one of the best sushi restaurants in New York to cater the meal.

They were not the only team to resort to extraordinary measures.

Yamamoto’s first visit was to San Francisco. The Giants had spent considerable time in Japan during the regular season, Wolfe said, and the pitcher wanted to return their respect. Yamamoto also had visited the city previously, and thought it beautiful, comparing it to Osaka.

The Giants hosted Yamamoto in a luxury suite, with lunch provided by a top Japanese restaurant in San Francisco, and set up a walk-through for Yamamoto at the Warriors’ practice facility inside the Chase Center. Yamamoto shot baskets, but did not meet Steph Curry and Co. — the team was on the road. The get-together lasted considerably longer than the one the Giants had with Ohtani, which consisted only of lunch with a small group in the clubhouse, at his request.

The Red Sox also impressed Yamamoto, who, seeking to play for a winner, was intrigued that chief baseball officer Craig Breslow, manager Alex Cora and pitching coach Andrew Bailey all played for Red Sox teams that won World Series titles.

The Phillies, trying to sell Yamamoto on the enthusiasm of the Philadelphia market, showed him a chart detailing how the reaction of fans to a home run by Kyle Schwarber in the 2022 World Series registered on the Richter scale.  Bryce Harper spoke to Yamamoto on a FaceTime call for approximately 30 minutes, emphasizing that Yamamoto needed to do what was best for his family and career, but talking up Philly, too.

“If you want to be in this market and play in front of this fan base, you’re going to reap the rewards of that,” Harper recalled telling Yamamoto. “We’re different than L.A. We’re different than New York. We don’t have that hoopla, the bright lights. But it’s a lot brighter in Philly in October than in any of those other places.”

President of baseball operations Dave Dombrowski, however, sensed his club was a longshot. “We quickly knew we were not one of his top suitors,” Dombrowski said.

Some with the Giants thought their chances of signing Yamamoto were good until Ohtani joined the Dodgers. But in the end, Yamamoto’s decision came down to the Dodgers and Yankees. And Friedman said the old notion that one Japanese star would not want to be teammates with another seemed to diminish after Japan’s triumph during the 2023 World Baseball Classic, where both Ohtani and Yamamoto played major roles for their country.

Ohtani was one of four Dodgers who had lunch with Yamamoto during his visit to Dodger Stadium, along with Freeman, catcher Will Smith and pitcher Bobby Miller. As each sat with their customized lunch — the Dodgers prepared Yamamoto a personalized bento box — they made their pitch. Mookie Betts later met Yamamoto, too, at a Lakers game, chatting at halftime and again once the buzzer sounded.

Freeman told Yamamoto that playing for the Dodgers, in front of nightly sellouts of 56,000 in the only stadium with four decks, was the “peak” major-league experience. Yamamoto seemed to get the message. “Watching him step on the Dodger Stadium mound for the first time and looking around, I could see the look in his eyes that he was pretty amazed,” Miller said.

The Yankees made a 10-year, $300 million offer that included a higher average annual value than the Dodgers’ proposal, an earlier opt-out and more money in the first five years, according to sources briefed on the respective bids.  Yamamoto chose the Dodgers’ 12-year, $325 million deal.

Wolfe said the bidding need not have ended there.

“I think this could have kept going, but Yamamoto was comfortable with where we were and said, ‘I’ve decided this is where I want to go, this is enough,’” the agent said.

If the Dodgers had stopped with Yamamoto, they still might have been projected to win 100 games for a fourth straight season and reach the World Series. But they continued to pour it on during the winter, signing former All-Star Teoscar Hernández, left-hander James Paxton, utility man Enrique Hernández and, of course, retaining future Hall of Famer Clayton Kershaw. Then, on the eve of their domestic opener, they agreed with catcher Will Smith on a 10-year, $140 million extension.

Just like the party at Paisley’s barn, the craziest offseason never seemed to end, raising the bar for the Dodgers even higher. As their fraught opening week in Seoul showed, the focus on this club is extreme, the stakes elevated to a new level: You do all this, you must win. The end result would be a World Series ring for all those involved — heck, perhaps even Paisley.

“Print that,” Paisley said. “Absolutely.”

(Top image: John Bradford/ The Athletic; Photos: Mary DeCicco / Getty Images; Chung Sung-Jun / Getty Images)