{"id":523246,"date":"2026-01-16T10:00:17","date_gmt":"2026-01-16T10:00:17","guid":{"rendered":"https:\/\/www.rawchili.com\/mlb\/523246\/"},"modified":"2026-01-16T10:00:17","modified_gmt":"2026-01-16T10:00:17","slug":"why-the-red-sox-should-have-learned-their-scott-boras-lesson","status":"publish","type":"post","link":"https:\/\/www.rawchili.com\/mlb\/523246\/","title":{"rendered":"Why the Red Sox should have learned their Scott Boras lesson"},"content":{"rendered":"

The Alex Bregman press conference<\/p>\n

The Alex Bregman drama has been analyzed and picked through since word came down Saturday night that he would be signing with the Cubs.<\/p>\n

There was the Red Sox’s unwillingness to include a no-trade clause, which the Cubs ultimately put in their five-year contract proposal. Some debate surfaced over if Boston’s $165 million offer was peppered with too much money in deferrals. And then there was the communication as all sides approached the finish line.<\/p>\n

Did the Red Sox not believe Scott Boras when he told them there was a better offer on the table? If so, history would have suggested that would have been a mistake. Just ask former Red Sox assistant GM Zack Scott, who immediately thought of another free agent negotiation upon hearing the Bregman situation.<\/p>\n

“The Teixeira one actually came to mind as it relates to the Bregman situation with the Red Sox,” said Scott when appearing on the Baseball Isn’t Boring Podcast.<\/p>\n

The “Teixeira” Scott referenced was Mark Teixeira, who faced the choice between the Red Sox and the Yankees as a free agent heading into the 2009 season.<\/p>\n

On tomorrow’s @BBisntBoring<\/a>, @ZackScottSports<\/a> offers some great insight, including why you shouldn’t doubt Scott Boras when he said he has a better offer.
Subscribe: https:\/\/t.co\/Tp3r2VAz90<\/a> pic.twitter.com\/wyxxTfKRDt<\/a><\/p>\n

\u2014 Rob Bradford (@bradfo) January 16, 2026<\/a><\/p>\n

For a good stretch, it represented the one big free agent the Sox truly prioritized that they didn’t reel in, with the first baseman signing an eight-year, $180 million deal with New York. Scott remembered the back-and-forth between the Red Sox and Teixeira’s agent, Boras, at the time, and couldn’t help but reflect on the lesson that was learned.<\/p>\n

“I have no idea if what’s out there is true in terms of what they offered or that they didn’t believe Scott had something better,” Scott said of the Red Sox’s dealings in the Bregman scenario. “But, you know, we kind of called Scott’s bluff with Teixeira and then realized, oh no, he did have something better with the Yankees. To me, I learned a lesson, and I’m sure others did too.<\/p>\n

“When you get down to it, sure, Scott, like a lot of agents, is going to say, ‘It’s going to take this, you know, at least this many years, and it’s going to take these kinds of dollars.’ But he’s not making stuff up when he says, ‘I have this. Right? There’s a difference between saying, ‘This is\u00a0what it’s going to take versus, ‘I have something that we think is better.’<\/p>\n

“So if you’re going to play … they should have taken that as word because I learned that lesson from our process with Teixeira that he’s not making that part up. …. It all worked out for both teams, but it just felt like it was a gut punch when we didn’t get him.”<\/p>\n

Seventeen years later, it’s a feeling the Red Sox were reintroduced to.<\/p>\n