Scott Boras Has a Monopoly Over This Year’s Free Agent Market

The winter meetings kick off next week, which means some of baseball’s biggest free agents could soon find their new homes. These meetings are when front office executives, owners, and agents come together and discuss potential deals as they work to improve their roster for the upcoming season.

These annual gatherings are important for building the foundation for key roster transactions, such as blockbuster trades and marquee free agent signings. Having some of baseball’s most important names all assembled in one place tends to get the ball rolling on deals at a much quicker pace.

One of those key names who will be present at the winter meetings is agent Scott Boras. Boras is one of the most prominent and influential sports agents, and he is notorious for earning his clients extremely wealthy contracts.

This offseason, Boras’ influence will be particularly impactful on how free agency could unfold. Specifically, he represents many of the top free agents on the market, including star players such as Cody Bellinger and Blake Snell.

This isn’t the first time he has represented a good chunk of the top free agents, however. As Ken Rosenthal pointed out in Monday’s edition of Fair Territory, he was in a similar situation at the winter meetings back in 2019.

That year, notable stars such as Gerrit Cole, Anthony Rendon, and Stephen Strasburgh were all free agents looking for luxurious deals. They were some of the biggest names on the market, and they were each represented by Scott Boras.

Consequentially, each player signed monster deals within three days of each other. Cole signed a nine-year, $324 million deal with the New York Yankees, Rendon signed a seven-year, $245 million contract with the Los Angeles Angels, and Strasburgh signed a seven-year, $245 million deal with the Washington Nationals. All three players signed within three days of each other, and it all transpired during the winter meetings.

Point being, Boars could be in a very similar situation next week at the annual gatherings. He represents some of the top names on the market, and there will be high demand for each of them. That means Boras could control the pace at which free agency unfolds not just for his players, but for all free agents. He could also have a very strong influence in setting the bar for market prices.

Boras’ Positional Players

As the winter meetings approach, Boras represents five key positional players in the free agent market this offseason. They are some of the best options at their respective position, and they will each warrant hefty deals this winter.

Of all the positon players that Boras represents, Bellinger could be the one to sign a deal worth over $200 million. However, given the risk that comes with signing a player with his kind of performance history, there have been a wide range of projections for what Bellinger’s upcoming multi-year deal could look like.

That said, one thing is for certain: Boras is going to get the most that he can for his coveted slugger. There will be high demand for Bellinger, and he could be Boras’ diamond in this year’s free agent class.

Matt Chapman is another name on this list who will warrant a huge multi-year deal. He is the clear-cut premier option at third base in this free agent class, and he is going to get paid like it. Checking in at No. 8 on Just Baseball’s Top-25 free agent list, Chapman is, without a doubt, one of Boras’ biggest clients this winter.

Rhys Hoskins will be another interesting name to follow this offseason. To most, he’s the top first baseman on the open market, and he has a long list of potential suitors who will be seeking his impactful bat. He comes with risk, as he missed the entire 2023 season with a torn ACL, but he has a track record of being a forceful power bat in the middle of the lineup.

J.D. Martinez is also one of the top bats on the market, as he is coming off a tremendous bounce-back campaign with the Los Angeles Dodgers. The six-time All-Star is one of the top designated hitters in free agency, and he proved in 2023 that he can still be a threat at the plate for a contending club. At 36 years old, his contract length will have a cap, but he will be receiving a high average annual value on his upcoming deal.

Finally, KBO star Jung Hoo Lee is flying under the radar as one of the best free agents available. He is certainly the top positional player in the class of international free agents, and he will be compensated as such. He provides strong bat-to-ball skills in the lineup to go with promising defense in the outfield. With the free agency class being relatively weak among position players, Jung Hoo Lee is one of the better outfield options available.

Starting Pitchers

Similar to the list of positional players, Boras represents two of the top starting pitchers in free agency as we approach the winter meetings.

The first of Boras’ top pitchers found a new home late on Tuesday night, when Nick Martinez signed a two-year, $26 million deal with the Cincinnati Reds. Martinez had a successful two-year tenure with the San Diego Padres, pitching to a 3.45 ERA and a 4.17 FIP across 216.2 innings with the club.

Outside of NPB superstar Yoshinobu Yamamoto, who is in the conversation for best pitcher available in free agency, Blake Snell and Jordan Montgomery are the two premier options on the open market.

Snell brought home the NL Cy Young Award after turning in an impressive 2023 season with the San Diego Padres. He pitched to an MLB-best 2.25 ERA with a K/9 of 11.70 and a whopping 31.5% strikeout rate. It’s no secret that walks were a concern, as he posted a 13.3% walk rate to go with a 4.95 BB/9, but the free passes clearly didn’t hamper his dominance on the mound.

On top of him coming off a career-type year, there is an abundance of teams in dire need of starting pitching help this winter. Snell is a key name in this free agency class, and Boras will ensure he gets paid like a two-time Cy Young Award winner.

Jordan Montgomery is behind Snell in the free agent rankings, but he will still be getting a monster deal this winter. Montgomery was traded from the St. Louis Cardinals to the Texas Rangers at the deadline, and he was elite down the stretch for the World Champions.

The left-hander posted a 2.79 ERA and 1.19 WHIP in 67.2 innings with the Rangers, and he played an essential role in their World Series title run.

He doesn’t have the ace-like pedigree that Snell has, but he’s going to get paid like one of the best pitchers on the market after a spectacular second half of the season.

Given that they are two of the top starters available, and that they are both represented by the same agent, I anticipate Snell and Montgomery to sign within a few days of each other when the time comes.

It’s going to be fascinating to see how free agency unfolds once the winter meetings begin.

Scott Boras has the opportunity to take some marquee names off the market in just a matter of days, or he can slow play the signings until he feels his players are given the proper deal. With Boras representing a good portion of the top players available, free agency could run on his time this offseason.