The most recent offseason was undoubtedly disappointing for the players on the whole. Many of them signed deals well south of expectations, with the most high-profile examples being the so-called “Boras Four”. Each of Blake Snell, Jordan Montgomery, Matt Chapman and Cody Bellinger, who are all represented by the Boras Corporation, lingered on the market deep into the offseason and ultimately signed deals below industry forecasts, though with opt-outs that will allow them to retest free agency in the future.

The two pitchers in that foursome evidently have different feelings about how this played out, based both on their actions and their words. Montgomery landed a one-year, $25MM deal with the Diamondbacks that didn’t become official until March 29. The deal also contained a $20MM vesting player option that Montgomery could unlock with at least ten starts in 2024, with his 18th and 23rd starts also adding $2.5MM to the option. On April 11, less than two weeks after that deal was signed, it was reported that Montgomery had switched his representation from Scott Boras to Joel Wolfe and Nick Chanock of Wasserman.

“I don’t know, obviously Boras kind of butchered it,” Montgomery said last week, per Mac Cerullo of the Boston Herald, “so I’m just trying to move on from the offseason and try to forget it.” Montgomery adds that, to his knowledge, he didn’t receive an offer from the Red Sox in the winter.

“Yeah, for sure. Me and my wife loved it here. She was at Beth Israel for a year, love the area, love the fans,” Montgomery said when asked whether he would have considered an offer from the Sox. “It would have been awesome if it had worked out that way, but it didn’t.”

The Herald also received a comment from Boras himself in response. “I saw what Jordan said. I know what it is to be frustrated with this game. As a former player I feel for him. But I’m also a lawyer with obligations to my clients, including former ones. So I cannot discuss what happened or the decisions Jordan made unless he gives me permission,” Boras said. “If he gives me the green light I’ll be happy to talk about it. I’ve been doing this for over 35 years. I relay all offers and relevant information to all my clients and act at their direction. They make all decisions. We wish Jordan well.”

Montgomery was frequently connected to the Red Sox both because the club was in need of starting pitching and because his wife was working in the area, as he mentioned. Most reporting throughout the offseason suggested that the two sides weren’t close to agreeing on a deal. In early March, Jon Heyman of The New York Post reported that the two sides were in contact but that Montgomery was looking for a seven-year deal that the Sox didn’t want to give out.

We can’t know for sure what sorts of discussions were taking place between Boras and the Red Sox, or any other teams, but Montgomery is clearly not thrilled with the way it played out. Not everyone places the blame on Boras though, as Blake Snell is still a Boras guy and defended him when asked about the Montgomery comments.

“My experience with Scott has been great,” Snell said yesterday, per Andrew Baggarly of The Athletic. “He told me everything that was happening, all the offers I got. So for him to just get bashed for what I believe is false, that’s not fair at all. I really strongly believe that.”

When asked about Montgomery’s tough time, Snell responded thusly: “He signed the deal that he ultimately wanted to sign,” Snell said. “He has the choice. I don’t know what other deals he was offered, but I know everything that was offered to me. It’s just sad that he thinks that way when I see Scott as a very honorable man.”

Boras has a lengthy track record of securing huge deals for his clients but it’s possible that he still could have whiffed on the recent offseason, which Snell was asked about. “Yeah, or it could just be a free agency where no one was really pushing to get anybody,” said Snell. “It sucks because that was … our year to get our deals that we worked so hard to get. But ultimately the market’s the market. You can’t control it. You can’t get upset about it the way it is. Just pitch better, find a way to do better, continue to compete. Whatever you believe you deserve, you go earn it.”

There is some logic to Snell’s framing of the winter, which was mostly defined by a lack of spending. Only four free agents got nine-figure deals in the winter, as shown on MLBTR’s Contract Tracker, compared to nine in the previous offseason. Of the four from the most recent winter, three of them were fairly unique cases. One of those was the mega deal for Shohei Ohtani, who is an unprecedented talent. Two others were for 25-year-olds coming over from Asia: Yoshinobu Yamamoto and Jung Hoo Lee. The fourth was for Aaron Nola. The rest of the market was modest, with solid regulars like Amed Rosario, Jurickson Profar, Randal Grichuk, Michael A. Taylor and others getting $4MM or less. It would appear that Montgomery believes Boras could have handled that environment better while Snell simply views it as something that was beyond his control.

In addition to their differing opinions about the past, both players now appear to have divergent future. Montgomery has struggled badly with the Snakes this year and was recently moved to the bullpen. As of today, he has a 6.44 earned run average through 95 innings and 19 starts. Unless he turns things around dramatically in the coming weeks, it would appear his best course of action is to take his player option and hope for better results in 2025. By making at least 18 starts this year, he has unlocked that option and raised the value to $22.5MM.

Snell, on the other hand, has been on fire after a slow start. By the end of June, he had two stints on the injured list, six starts and a 9.51 ERA. But he came off the IL in early July and has posted a 1.30 ERA in his nine most recent starts, including a no-hitter against the Reds earlier in August. The lefty signed a two-year, $62MM deal with the Giants that allows him to opt-out at season’s end. He could trigger a $30MM player option for 2025 but could also walk away with $32MM banked and then take another shot at free agency.

If he keeps putting up good numbers for the next few weeks, it’s highly likely that another trip to the open market is in the cards. Speaking of the rest of the season, Snell says that “I’ll enjoy those starts and make the most of them and we’ll figure out what happens after that later,” before adding that he has high confidence in Boras to handle whatever comes next. “Of course,” Snell said. “High confidence. Really high.”

Boras tends to be a polarizing figure in baseball circles, so the struggles of the “Boras Four” led to a lot of schadenfreude and declarations that he was “washed” or over the hill. However, Boras is well set up to be a key player in free agency again this winter. Snell, Chapman and Bellinger will all have chances to return to the open market, while Boras also represents big-name players slated for free agency this winter such as Juan Soto, Corbin Burnes, Alex Bregman, Pete Alonso, Yusei Kikuchi, Sean Manaea, Tyler O’Neill, J.D. Martinez and many others. What those players will be entering another frosty market or not remains to be seen.