Red Sox Rumors

Zack Scott is a 4x World Series Champion with the Red Sox and former Mets Acting GM who applies championship leadership principles across professional sports and corporate environments. As Founder & CEO of Four Rings, he consults with teams like the 2023 World Series Champion Texas Rangers while coaching senior executives at growing companies to build winning leadership cultures. He also founded The Sports Ops Launchpad, helping aspiring sports ops pros break into the industry with a proven 20x success rate.

I’ve been in war rooms where a single phone call can change three franchises, end careers, or create legends. Most of the time, though, absolutely nothing happens.

I spent 20 consecutive years in trade deadline war rooms, including 17 with the Red Sox and one each with the Mets, Pirates, and Rangers. The reality is more mundane and less dramatic than fans probably expect.

How the War Room Works

The real work starts weeks before the deadline. For much of my career, a big part of the job was ensuring decision-makers were prepared when deals started moving. We gathered performance analyses, scouting evaluations, contract data, medical history, makeup reports, and intelligence on who was buying, who was selling, and what each team wanted.

The trade deadline has a unique rhythm. Long stretches of nothing, then everything happens at once.

You’ll sit in a conference room, which typically includes the GM, assistant GMs, scouts, analytics staff, and other baseball ops folks, for hours making small talk, going over the same reports, and waiting for phones to ring. Some GMs set up too early, and you end up with a room full of people staring at each other for weeks.

Most of the time, we’re doing exactly what fans do: refreshing MLBTR and X, hoping to catch something we missed.

But then something shifts in those final hours. Teams that were “just checking in” suddenly get serious. The pace picks up, conversations get urgent, and that’s when the real drama begins.

When Every Second Counts

People think the 6 PM deadline is just a formality. It’s not.

I’ll never forget when we traded Nomar Garciaparra. Hours of waiting, scattered conversations, then suddenly we’re in a four-team deal with the clock ticking down to the final minute.

This was the face of the franchise, with multiple teams trying to coordinate. Someone called out: “We’ve got ten minutes!” You have people on phones with different teams, trying to ensure everyone’s on the same page while the minutes disappear.

We got it done, but barely. Those kinds of deadline deals show you who can handle pressure and who can’t.

The Human Side of Historic Trades

Not every great trade comes from sophisticated analysis. Sometimes it’s about delegating and setting others up to succeed.

The Dave Roberts trade almost didn’t happen. And if it hadn’t, the 2004 Red Sox probably wouldn’t have become the first team in history to come back from down 3-0.

Theo Epstein asked an intern to research available outfielders. The initial list was terrible, but instead of dismissing it, he challenged the young staffer to think differently. That’s when the intern heard the Dodgers were trying to acquire Steve Finley. Since they already had plenty of outfield talent, maybe they’d be willing to trade away Dave Roberts. The intern rushed to Theo’s office with the idea. Within hours, we’d made the trade.

You know how that story ended—bottom of the ninth, Game 4 of the ALCS. Roberts steals second, scores the tying run, and we complete the greatest comeback in baseball history. That trade happened because Theo had created an environment where everyone’s input was valued.

When Deals Fall Apart

But not every story has a happy ending. You can get so close to a franchise-changing trade, then watch it disappear overnight.

In 2009, we had a three-team deal almost done: Adrian Gonzalez from San Diego to Seattle, Felix Hernandez from Seattle to us, and several young players, including Josh Reddick, Daniel Bard, and Justin Masterson, going to the Padres.

Seattle’s GM slept on it, then decided he couldn’t move the King. Just like that, a deal that could have changed three franchises was dead.

When Everything Gets Complicated

The complexity isn’t always about multiple teams. It can be about competing priorities and external pressure.

In 2008, we had to move Manny Ramirez. He was threatening not to play for us if we didn’t trade him. As defending champs with aspirations to repeat, we couldn’t just give away a great hitter. We needed to find another impact player to replace him.

That’s how Jason Bay entered the picture, but it required multiple teams to make it work. We had two options: get an established impact player like Bay, or ask for a prospect who wouldn’t help us immediately. At one point, we even asked the Marlins for 18-year-old Mike Stanton (now Giancarlo) straight up for Manny. That move would have hurt us immediately but helped us in the long term. That took huge stones to even consider.

The situation became a stalemate that required Commissioner Selig to mediate. We finished after the deadline, but Selig allowed it because he felt it was in the best interest of the game. We got it done: Manny to LA, Jason Bay to us, and prospects to Pittsburgh.

When I Finally Ran a War Room

When I became Acting GM at the Mets in 2021, I finally got to run a war room. After 17 years of observing various approaches, I had developed clear ideas about how to do it effectively.

I kept multiple conversations going simultaneously because more opportunities meant a better chance of finding the right deals. I also made sure we had a room packed with people, because I’d learned that good ideas can come from anywhere. But instead of letting people sit idle, I came prepared with specific questions and tasks for each staff member throughout the day.

The challenge was that we were working with incomplete information: missing projection systems, gaps in scouting reports, and limited data on our own prospects. We were trying to rebuild these systems while competing for a playoff spot.

That pressure led to trading Pete Crow-Armstrong for Javy Baez and Trevor Williams, players who made a positive short-term impact. Even with our limited information, the underlying intelligence suggested the long-term risk was higher than the expected short-term gain. But being in first place created enormous pressure to improve immediately. I chose the short-term need over long-term value, and I own that decision.

It taught me that no matter how well you structure your war room, external pressure can still override your process.

What Really Matters

A trade deadline war room is loaded with technology, including multiple screens, databases, and video systems. But here’s what I learned after 20 years. The deadline isn’t just about having the best information. It’s about creating an environment where the best ideas can come from anywhere.

The deals that change franchises often come from unexpected places. That’s what makes it electric and maddening all at once.