Trevor Plouffe’s second act as Jomboy’s baseball insider (2024)

Trevor Plouffe was all business. Making the short drive from his home in Hidden Hills, Calif., to meet a few internet friends at a nearby gastropub one day last winter, Plouffe was planning a pitch: the former Major Leaguer wanted to invest in Jomboy Media, the burgeoning network of baseball podcasts and web shows popularized by Jimmy “Jomboy” O’Brien’s breakdown videos.

Plouffe hadn’t mentioned investing when he had suggested to O’Brien that they grab a beer when the Jomboy Media team was in Southern California. But while Plouffe was still in the car, his iPhone rang. An old buddy on the other end of the line said, “Hey, I heard you’re meeting up with Jomboy.” Plouffe was, but he hadn’t told anyone about it. “Wait,” he replied. “How did you know?”

Turns out, the friend had formed a strategic investment group and had just met with O’Brien, his brother, Lucas, and Jomboy partner/podcaster Jake Storiale.

“So, they kind of beat me to the punch,” Plouffe said, with a laugh, in a lengthy phone conversation with The Athletic late last month. “I was like, ‘Man, do me a favor. If you can, shuffle some things around. I want to be involved in that. Let me meet these guys, and if I like them then I want to be in this group.’”

Plouffe liked them. A couple of beers turned into Plouffe inviting Storiale and the O’Brien brothers to a neighborhood barbecue he was having the next day.

“We became fast friends,” Plouffe said. “Now we talk to each other every day.”

“It was as simple as that,” O’Brien said.

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Enjoy fighting back tears.

A post shared by Talkin’ Baseball (@talkinbaseball_) on May 18, 2020 at 1:24pm PDT

Plouffe joined the investment group. (The financial figures of Jomboy Media’s latest round of funding have not been disclosed.) Plouffe, however, had another ask. He wanted to help the company grow from the inside. And that’s how after 14 years in professional baseball and one restless year of retirement Plouffe came to be outfitting his home office as a makeshift recording studio and starting his second act as a podcaster, YouTuber and Jomboy’s industry insider.

He’d soon discover that while staring down a 100 mph fastball is scary, it has nothing on scrolling through your Twitter mentions when fans and reporters have their sights aimed at your scoop. That, Plouffe admits, “was terrifying.”

When the Phillies extended a spring-training invitation to Plouffe in 2019, he informed them up front that if he wasn’t on the opening day roster, he planned to retire. Plouffe had decided he’d rather spend the summer with his wife, Olivia, and their young children, Teddy and Isla, than plug away again at Triple A. He played for the Phillies’ Triple-A team in 2018, ascending to the majors just long enough to smack one last homer, a 16th-inning walk-off against Dodgers utilityman Kiké Hernández. (This is still a point of pride for Plouffe: He was 2 for 2 with two homers when facing position players in his career.)

A former first-round pick, Plouffe, now 34, spent his 20s in the Twins organization. He was a steady if unspectacular corner infielder — the definition of an average hitter at 100 OPS+ over his six full seasons in Minnesota — until he hit 30 in 2016 and his batting numbers nosedived. Plouffe bounced around, from Minnesota to Tampa Bay to Texas to Philadelphia, as his career winded down.

Plouffe wasn’t surprised when he didn’t win a spot on the Phillies roster last spring. A few teams reached out to his agent, but Plouffe stuck to his word.

Walking away from baseball wasn’t a difficult decision; determining what to do next was. For six months or so, Plouffe hung out with his family, and they had the summer they always had wanted — vacations, weddings, cookouts. “Being home with them was all I really wanted to do,” he said. “And then it became apparent that I couldn’t just stay and do that forever. I needed to do something.”

The first business idea Plouffe looked into was a hemp oil production company. Then he considered real estate. Neither suited him. Too business-y, he said.

“When you spend your entire life in baseball, your entire network is in baseball and your area of expertise is in baseball, it kind of makes sense to pursue something in that realm,” Plouffe said. “So that’s when I started to look for some avenues in the media world.”

"I like reading Trevor Plouffe's stuff. He's got a lot of good takes."

Damn right he does… @trevorplouffe pic.twitter.com/NubMCiSV0Y

— Talkin’ Baseball (@TalkinBaseball_) October 15, 2020

Plouffe had always been interested in baseball media. He spoke with reporters regularly in the clubhouse, and he understood their job was to be even-handed. But Plouffe believed there were ways to break the traditional mold of how baseball was covered. In 2018, while he was still playing, Plouffe texted a couple of contacts at the Players Association about ways to diversify and enhance what fans see every day on MLB Network — small show tweaks; ideas to promote players; mixing alumni and current players more often. Plouffe hoped the common fan could learn to love the game and its players like he did.

“So, it’s been on his mind,” O’Brien said. “He knew he wanted to do stuff like this after he was done playing, way before he met me or probably even heard of me and Jomboy Media.”

This instinct makes Plouffe a natural fit with O’Brien and Storiale — two diehard Yankees fans whose content is peppered with unapologetic homer-ism — on their podcast Talkin’ Baseball. The three of them don’t pretend to be objective. They’re just baseball fans with microphones and an audience. Plouffe calls it “fan media.”

“I’ve been pretty vocal about wanting to change baseball’s relationship with the media because we have such superstars in the game that just don’t get represented the way they should,” Plouffe said. “There are definitely more and more (people) coming on the scene who promote the players and do it in a fun way that I think is very engaging for the fans. And the medium they do it on — YouTube and all the socials — is the way content is consumed.”

But what first connected Plouffe and Jomboy Media wasn’t a shared vision. It was the Astros scandal. After The Athletic’s initial report about the Astros’ electronic sign-stealing scheme, O’Brien turned visual evidence into a trademark breakdown video, which has accumulated 5.2 million views. That’s when Plouffe started direct messaging O’Brien with tips he was hearing from active players. They messaged back and forth for weeks, sharing potential leads — the first step in the partnership between @Jomboy_ and @trevorplouffe.

“In the moment, it was terrifying.”

Plouffe posted the tweet and held his breath.

Want some good baseball news??

I just heard from multiple sources that on June 10th, Spring Training 2 will start. July 1st will be Opening Day and all teams will be playing at their home ballparks.

We’ll be discussing it in full on the next @TalkinBaseball_

— Trevor Plouffe (@trevorplouffe) May 4, 2020

Plouffe was giving a glimmer of hope to the shuttered baseball world. Players had continued telling him their suspicions about sign-stealing throughout the offseason, and so once MLB-MLBPA labor negotiations began this spring, Plouffe had an avalanche of sources staying in touch. (This intel turned into a recurring segment on Talkin’ Baseball: “Trevor’s Tidbits.” It has a theme song.)

On this particular day in May, Plouffe says, players from three different teams informed him that their organizations were telling players to be ready to start spring training June 10 in advance of a July 1 opening day. Plouffe figured he had the scoop nailed. He texted with O’Brien to make sure he had the proper wording. Then, Plouffe said, “we were like, all right, man, let’s go with it. We both knew that if I tweeted it out, it was going to be crazy.” And it did.

Then came the blowback. Rather than confirm Plouffe’s report, insiders shot it down. Plouffe’s Twitter mentions were a mess. The next day, The Athletic’s Ken Rosenthal reported that officials from at least one team, the Indians, had indeed indicated to players that July 1 was a target date for opening day, with a three-week ramp-up period starting June 10. But, Rosenthal added, the officials said those dates were simply targets, fully expected to change.

Ultimately, Plouffe learned a lesson in specificity. The dates he had mentioned were being discussed as MLB formed a proposal, but they were not set in stone.

“Could I have worded my tweet better? Yes,” Plouffe said. “I could have left myself outs and said, like, ‘tentatively’ and all those words that leave you outs. But we didn’t do it. Partly because we’re not versed in that language, I guess.”

At the same time, Plouffe says in retrospect he wouldn’t change a thing.

“It was a tough few days for me because everyone was basically talking sh*t about me,” he said. “Then there was some confirmation. It felt good to have that. And then, as we learned, the situation was so fluid. Any information that came out probably wasn’t going to be right.

“I want to make this point, too, because I got yelled at and scolded about how I should have gone about things and how it was irresponsible. After I did that, pretty much all the people that told me it was irresponsible did the exact same thing over and over again during the negotiations. There were no hard truths during the pandemic and the negotiations that followed. It was a lot of fluidness. I got a lot of crap. … I learned some things, but I also learned that people are quick to point out your mistakes and don’t care about their own.”

Plouffe offers the baseball media scene something few others can: the players’ perspective, from a former player still seriously plugged in. It helped this summer. Plouffe had some experience with the drudgery of MLB-MLPA negotiations, which in this case dragged on for another 50 days after his tweet. Plouffe was a long-time assistant union rep for the Twins, and he was part of a bargaining committee for the last collective bargaining agreement. So, the podcast became a space to try simplifying baseball’s power struggle for its fans.

“We called ourselves a labor-negotiation pod,” Plouffe said. “We didn’t like doing it. We didn’t want to do that. But the situation just kind of dictated it, so we just ran with it, man. It was exhausting. We knew we wanted to keep people informed and not just have them say, ‘Who cares about billionaires versus millionaires?’ I actually really resented that sentiment. Like, I get it. But this is the industry you’re interested in. Let me explain why this was happening.”

At some point, though, fans lose their appetite for labor disputes.

Since Plouffe also has a player’s connections, he put his network to work. Talkin’ Baseball pivoted to feature more player interviews during the shutdown, and Plouffe started the YouTube show “Sequence,” in which he enters the virtual film room with a player to break down their most memorable at-bats. The guest list includes a mix of Plouffe’s friends from Southern California, former teammates and young players just getting their start in the majors.

On the air, Plouffe comes across like a big brother to the younger players. He asks about their transition to the big leagues and what it’s like trying to find their feet on the fly. He remembers that rookie jump and how a slow start can sow doubt and confusion. Depending on the guest, Plouffe dispenses the type of advice he heard from veterans like Jim Thome, Justin Morneau, Joe Mauer and Michael Cuddyer when he debuted for the Twins 10 years ago.

“I like to highlight some guys that wouldn’t necessarily be highlighted,” Plouffe said. “I don’t want to do just the Yankees and the Dodgers. I want to highlight some other guys that aren’t going to get hype, and that includes young guys. Cole Tucker came on and was talking about Ke’Bryan (Hayes). We got Triston McKenzie on really early. The game is just turning younger, and you usually hear from established guys who are doing really well. It’s fun to hear the other side of that. Like, Hey, I’m just here and I’m trying to figure things out.”

“He’s a pretty good hype man for these kids,” O’Brien said. “We live in such a confidence-driven world, and I think Trev sees that and says, ‘Why would I not try to gas these guys up and get the best out of them? The other side seems pretty negative and uninteresting.’”

Plouffe said he isn’t sure how Sequence will evolve. He wants to fine-tune it for viewers while making it feel like when he and his teammates would analyze pitch sequencing in the video room before games. (Or, even before the Twins had a video room, Morneau would study at his locker with a laptop and a memory card.) It’s a little different when you’re on opposite ends of a video call, but it still scratches the itch. Pirates pitcher Chris Archer moved into Plouffe’s neighborhood recently. Plouffe got him on Sequence a couple of weeks later.

This postseason, the podcast with O’Brien and Storiale has kept Plouffe busy. After the wild-card round, Plouffe opened the next episode with a paper bag over his head. He had picked the Twins over the Astros. After the Twins melted down, Plouffe tweeted. “I didn’t think it would feel this bad.” He’s an investor and insider now, but beneath all of that, he’s still just a big fan.

(Top photo: Brace Hemmelgarn / Minnesota Twins / Getty Images)