Does Scott Boras Only Win Free Agency When Dealt a Great Hand?

There may never be another sport agent like Scott Boras. A career that spans more than four decades, it is not far-fetched to say that Boras has been one of the most influential figures in the history of Major League Baseball.

From his start representing Manny Trillo, to Greg Maddux, Kevin Brown and eventually Alex Rodriguez, Boras has helped manage the careers of some of the greatest players of all-time. He has set and broken his own contract records countless times over, and even to this day, represents some of the game’s very best players.

His ability to get top dollar was on full display this winter, when he held a silent auction for Juan Soto, never letting the numbers leak on what each team was bidding, as if the 26-year-old outfielder was a piece of fine art.

Boras ultimately found the ideal collector for such a piece of art, with Mets owner Steve Cohen winning the final bid to the tune of $765 million over a 15-year deal.

This contract is the richest in the history of American sports and surpasses Shohei Ohtani’s $700 million deal from an offseason ago by over $300 million in terms of present day value, as not a penny of Soto’s contract is deferred.

Would any other agent have gotten his client such a great, and quite frankly, ludicrous deal?

Probably not.

With that said, Boras does not come with out faults, as this is now the second offseason in a row where a few of his top clients remain unsigned with Spring Training fast approaching, where they may soon be forced to take a deal that is far-less than they once hoped.

In the case of Pete Alonso and Alex Bregman in particular, is Boras responsible for stalled markets where ill-advised tactics have put his clients in a bad place? Let’s explore the latest to find out.

Pete Alonso Should, But Might Not, Be a Met

When free agency began, if there is one thing most prognosticators agreed on, it was that Pete Alonso should re-sign with the New York Mets.

A beloved homegrown Met, who will likely break the franchise’s all-time home run record if he spends just one more season in Queens, Alonso has expressed his interest in remaining with the only franchise he has ever known at every turn.

The 30-year-old slugger is coming off a fantastic playoff run, which saw him hit one of the biggest home runs in franchise history. In a do-or-die Game 3 of the Wild Card round, Alonso hit the game-winning blast off Devin Williams in the ninth inning with the Mets down to their final outs.

He proceeded to post a .999 OPS in October, showcasing just how big his bat can play during the biggest moments. With that said, Alonso’s regular season numbers have been on the decline over the past few seasons, and the market for first basemen is not what it once was.

This has led to an very unfortunate offseason for Alonso, who has seen the first base market move around him, with no teams expressing interest in signing him to a long-term deal.

Other top free agent first basemen Christian Walker, Paul Goldschmidt and Carlos Santana all signed in a 48-hour span, which also saw Josh Naylor get dealt from the Guardians to the D-Backs.

Jake Burger, Nate Lowe, and Spencer Horwitz have all been traded this offseason as well, with most teams having filled their first base vacancies with plenty of time to spare.

Whether it is because everyone assumed Pete was going back to the Mets, or was just wary of committing long-term years and big-time money to a right-handed slugger on the wrong side of 30, a market just never materialized for Alonso.

Much has been made of the fact that Alonso turned down a reported seven-year, $158 million contract extension back in 2023, but this decision is not one that has to be on Boras’ conscious.

Alonso was represented by a different agent at that time, and the Mets were being run by a different GM in Billy Eppler. Now under President of Baseball Operations David Stearns, the Mets have not been as willing to give out such a long-term commitment, even to a guy who Stearns has repeatedly called, “A Great Met”.

The situation Alonso finds himself in is due to series of circumstances that can’t entirely be pinned on Boras. Between the decision to decline the extension, a relative down year (postseason excluded), and a market that no longer values first basemen on long-term deals, Alonso has seen the deck stacked against him.

Also, it is hard to ignore the fact that Mets owner Steve Cohen just spent over three-quarters of a billion dollar on Soto, only to now be haggling Boras over a tens of millions of dollars on Alonso.

Still, as we look at what has turned into an ugly situation, Boras bears some blame for miscalculating Alonso’s market, where now they have been backed into a corner.

Before I get into ripping Boras for how he has misplayed this market, I must acknowledge that I too misread what the market would be for Alonso. In my free agent predictions article, I had Alonso returning to the Mets on a six-year, $140 million deal.

What I failed to realize at the time, is that the Mets would be bidding against themselves for Alonso, and Stearns planned to use every ounce of leverage he had to get a good deal on player he valued, but only at a specific price point.

Boras played this market as if he expected Cohen to come over the top and take care of Pete if he waited it out long enough. This has long been a pattern for Boras, of going above the head of a GM, and getting deals (and often player-friendly ones) directly from the owner.

While Stearns was clearly involved in the process of recruiting Soto and sharing the long-term vision of the Mets, it was Cohen who deserves most of the credit for getting that deal across the finish line.

Negotiating with Cohen is what Boras wants, but for Alonso, it has been very clear through reporting that Stearns is running the show. And one thing a talented young executive won’t do is bid against himself.

This is what led to a breakdown in talks, which now hopes of a reunion hanging on by a thread.

For most of the Mets free agents, the pattern for which they operate is that they will send them out into the market to assess what their value is, then look to re-sign them if they deem the price is right. This is how Brandon Nimmo signed a few years back, and just recently this landed Sean Manaea back in Queens.

What do Nimmo and Manaea share with Alonso, other than being teammates in 2024? All three are represented by Boras. The difference though is the market they each enjoyed, and the perceived star power that each had.

Nimmo was the top center fielder in free agency after having a career-year in 2022. This allowed him to land an eight-year, $162 million deal. Manaea was coming off a career-year as well, and he ended up signing a three-year, $75 million deal.

What is noteworthy about Manaea is that he was reportedly only offered one other contract deal in free agency, a three-year, $67 million deal with the A’s that ultimately went to his now former teammate Luis Severino.

The Mets were offered the chance to match the A’s offer on Sevy, and chose to pass up on that deal. Manaea had declined the offer first, and then waited around for three weeks without getting another offer before coming to terms with the Mets.

You could say Manaea’s patience was rewarded (and it was since he got to re-sign), but Boras did not really get any better deal than what had been offered to him by the A’s.

With $23.25 million deferred, the present day value of Manaea’s contract is right in line with what he was offered by the A’s. More money to be sure, but this is an example of the Mets meeting an established market price.

This brings us all full circle on Alonso.

Because Alonso never had a market develop, Boras’ tactics have been to leak reported interest from other teams, and then of course to just sit back and wait for Cohen and Stearns to get uncomfortable.

This led to a PR move by the Mets last week, where they signed Jesse Winker and had SNY’s Andy Martino report that this was he beginning of their “Plan B, Post-Alonso”, as they “expected him to sign with another team.”

Now this Plan B so far has just been Winker and left-handed reliever A.J. Minter, two additions that would not seem to impact the Mets ability to sign Alonso. But the public statement of being ready to move on was a measure to prepare fans for a potential departure, and a defiant stance that the Mets were ready to play hardball with one of their franchise’s beloved stars.

What is Fair Market Value for Pete Alonso?

The New York Post has reported that the Mets offer to Pete Alonso was a three-year deal with opt-outs in the “$68-70 million range”. SNY’s Andy Martino said on Thursday night that such a contract would have included deferred money, and the present day value would have been in that range.

This has all come after earlier reports that Alonso was offering himself to the Mets on an “exclusive” three-year deal with opt-outs.

We never learned exactly how much Boras was asking for, but it is fair to assume he expected more than the $80 million he negotiated for Cody Bellinger on a similar deal a year prior.

You might say, “what’s the difference in say, $70 million and $90 million over three years for Cohen?”

Well when you are a repeat tax offender, pushing up on the top tax line, every dollar spent costs 110 cents on that dollar in taxes. This means a cost in 2025 of roughly $61 million for Alonso compared to $46 million if we were to assume a difference of AAV from $30 million to $23 million.

Stearns is looking at making a good deal for this season, while keeping financial flexibility to pursue other big fish in years to come. He is also setting a precedent that Boras can’t always expect to set high prices for Cohen simply because he has the financial wherewithal to match them.

Alonso is the one that is caught in the middle of all of this, and now he may end up signing elsewhere, where a better deal might not exist.

The Blue Jays are the team that is being reported to have interest in Alonso right now, but Sportsnet’s Ben Nicholson-Smith and Shi Davidi have cautioned that no deal is imminent.

Toronto is fresh of signing Anthony Santander to a five-year, $92.5 million contract, which has a staggering $61.75 million of deferred money baked into the deal. This deferred cash allowed the Blue Jays to stay under the second threshold of the luxury tax (for now).

Are they really prepared to blow past that line, and potentially even the final threshold for Alonso?

More likely, if they signed Alonso, expect the deal to be in a similar price range to the framework that is already out there from the Mets. While a $23 million AAV feels light for Alonso, it is a raise on the $20.5 million he made through arbitration last year.

It is also right in line with what Christian Walker got in free agency, giving Pete slightly more than the three-year, $60 million deal his contemporary got from the Houston Astros.

When we just ranked the top 10 first basemen in baseball, our panelists had Alonso and Walker back-to-back in the rankings, and it was not a consensus pick that Alonso was better.

With no other team in the bidding, basing Alonso’s deal as a slightly better one than Walker, with the added flexibility of the opt-outs might be the best that he gets. Especially if he gets to hit behind Juan Soto to potentially inflate his numbers in another contract year.

If Alonso does better than that, maybe Boras wins when it is all said and done.

But this is certainly trending towards a big L for the Boras Cooperation, and if Alonso is wearing another uniform at the same or a cheaper price over ego and pride from contentious negotiations, everyone will be losers in this situation.

Not truly understanding the market for Alonso squarely falls on Boras’ shoulders, as does another potential breakup that could happen in Houston.

Why Isn’t Alex Bregman Re-Signed in Houston?

Just like how Pete Alonso is synonymous with the Mets, the same can be said about Alex Bregman with the Houston Astros.

Bregman is a two-time All-Star who has won two World Series rings with the Astros. One day, it is fair to think that his No. 2 could be hanging in the rafters retired by the team. Yet, he is still a free agent with February fast approaching.

Now Bregman’s situation is not nearly as dramatic as Alonso’s, as the Astros have played this market a bit more cut and dry than the Mets. They pursued Bregman aggressively early, offering him a six-year, $156 million deal to re-sign and continue to be their third baseman.

Boras advised Bregman to decline in hopes of getting a better, and potentially a longer deal, and the Astros wasted no time pivoting.

Houston traded Kyle Tucker in a deal that netted them Isaac Parades for the present, as well as top prospect Cam Smith, who could be the Astros future at third base. They later signed Christian Walker to that aforementioned three-year deal, locking in both corner infield positions.

Bregman has been on the market waiting ever since, and has yet to find a deal better than what was on the table to start the offseason. The Detroit Tigers and Boston Red Sox have been the two teams most often linked to Bregman, but no deal has been made.

This story took an interesting turn yesterday though, when it was reported by Chandler Rome of the Athletic, that the Astros offer to Bregman was still on the table.

In this scenario where Bregman returns, the move would apparently be to keep him at third base (where he just won a Gold Glove) and move Parades to second base. This would then shift future Hall of Famer Jose Altuve into left field.

According to Rome’s story, Altuve has been pleading for the franchise to retain Bregman, so he must be amenable to a position change if it means bringing his teammate back.

At this point, can Boras really turn down this offer again? And if he does, will Bregman sign for something better, or end up in worse situation on a similar if not a worse deal.

Verdict: Is Boras Washed?

There are $765 million reason to answer no to that question, but the situations with Alonso and Bregman are still worthy of criticism.

Ultimately Boras is greatest of all-time in this field, and his tactics can still get guys paid as evidence by Soto, Blake Snell and Corbin Burnes this offseason. He also did a nice job landing Yusei Kikuchi and Frankie Montas deals that were above their perceived market value.

If there is something we have learned about Boras over the last few offseasons, it is that he is misvaluing his fringe stars. While it might not be fair to categorize Alonso and Bregman in such a light, the market is not valuing these players to the same degree as they once did, and Boras’ old tactics have clearly fallen on deaf ears.

The top tier free agents are going to get paid regardless, and Boras has seemed to do a nice job with his B-tier free agents like Kikuchi and Tyler O’Neill.

It’s the A- to B+ guys who Boras seems to be a bit blind on, where those All-Stars used to always get paid on long-term deals, but now teams have wised up to the risks of players in their 30s.

Playing hardball and dragging your free agents deep into the winter and all the way to spring is worth it if your guys get paid at the end of the ordeal, but if not, you are basically taking these All-Stars and dragging them through the mud for no reason.

Sure, you can blame a market that doesn’t value these players as much as they once did, but if all 30 teams have come to a consensus, at a certain point the agent has to read the room.

Hopefully the stories with Alonso and Bregman have a happy ending where each gets to continue to author legacies with the only teams they have ever known. If not though, these guys may wonder what if for the rest of their careers.