Can Free Agent History Predict the Future for the Boras Four?

SCOTTSDALE, Ariz. – The first pop of the catcher’s mitt has officially kicked off Spring Training throughout Arizona and Florida. Pitchers and catchers have reported for all 30 clubs with position players set to arrive by the middle of next week.

This brings the offseason to an end, right? Thanks to agent Scott Boras — or thanks to the teams negotiating with him — four of his best clients are still free agents.

In addition to questions about every team’s bullpen and the health of the roster, everyone is discussing the fate of the Boras Four. Cody Bellinger, Matt Chapman, Jordan Montgomery and Blake Snell have yet to sign with a club despite being four of the best available on the market.

If you include J.D. Martinez, a designated hitter tied for the fifth-most home runs in MLB since 2017, then Boras still possesses a stable of superstars that can change the postseason odds of any team that acquires them.

Why The Long Wait?

Unless you’re a literal fly on the wall during those negotiations, it’s altogether unclear why these players remain available. An obvious reason is that the offers have not matched the perceived price. Teams are balking at the numbers being exchanged and the nibbles simply haven’t been strong enough to snag a suitor.

Speaking with those inside the game, there’s some belief that Bellinger and Snell — the best pedigreed hitter and pitcher this offseason not named Shohei Ohtani — have an idea where they want to play the next few years of their career. As higher profile players, this pair may be less willing to take the most money from a certain team or move to a location they don’t like.

Montgomery performed like an ace in 2023, especially when he elevated the Rangers rotation in the second half. Boras is almost certainly selling that story while teams are viewing him as more of a No. 2 or 3 starter.

Chapman is a perennial Gold Glove Award finalist who hasn’t been an All-Star since 2019. If you take Baseball Reference’s WAR, he’s tied for the 10th-highest in the game at 28.0 since 2018. If you’re an owner or a GM, you might balk at a price tag nearing $100 million for a player that hasn’t topped 27 home runs or 76 RBI in any one of his last three seasons.

The biggest complication for Bellinger, Chapman and Snell is that all three turned down a one-year, $20.325 million qualifying offer from their respective club. (Montgomery was ineligible to receive one as he was traded during the season.) With the financial cost of acquiring one of these players comes with a cost to the future of the franchise.

Any team that signs one of these players must forfeit an early round draft pick. The eight clubs that exceeded the Competitive Balance Tax threshold last season would lose their second- and fifth-highest picks, as well as $1 million from its international bonus pool for the next signing period. Revenue-sharing recipients would lose their third-highest selection while the rest of teams would lose their second-highest pick along with $500,000 from their international bonus pool.

A similar scenario played out in 2014 when two Boras clients, Stephen Drew and Kendry Morales, who held out through the start of the season. The pair eventually signed one-year deals in May and June, respectively, for less than the qualifying offer they had rejected, but close to the pro-rated value. Regardless, they received less than originally anticipated.

Past Successes for Boras

This isn’t the first time a top free agent has waited this long in Spring Training to sign with a club.

Bryce Harper signed a 13-year, $330 million deal with the Philadelphia Phillies on March 2, 2019. It set the record for largest overall contract at the time. Despite that fact, the deal came with zero player opt-outs and was without a no-trade clause. This may be one reason why he’s reportedly been interested in an extension with eight years remaining before he reaches free agency.

Four offseasons later, his $25.3 million average annual salary ranks 28th-highest for the 2024. Harper could have leveraged an opt-out in a similar manner to Manny Machado and his agent, MVP Sports Group. After his fourth season with the San Diego Padres, Machado signed a new 11-year, $350 million deal. The third baseman will earn $458 million by the time his deal in SoCal comes to a close.

Several other Boras clients came close to reaching or exceeding the expectations of MLB Trade Rumors’ predictions. Jackie Bradley Jr. did well to receive his money when waiting until the start of camp. The Milwaukee Brewers signed him to a two-year, $24 million deal on March 8, 2021, a full $8 million over MLB Trade Rumors’ projected contract.

Ultimately, the list of players who have waited around this long to land a suitable deal is dwarfed by the list of those who did not get such compensation.

The Biggest Failures for Boras

The 2017-18 offseason featured a similar situation to the one currently at play for Boras’ clients. Unfortunately for that year’s crop, it didn’t work out well. 

An increase of players who were non-tendered contracts flooded — and complicated — the free agent market that winter. So many were available when the calendar flipped to February that a free agent camp was created to accommodate these players. Eight of Boras’ best players were without homes: Mike Moustaka, Jake Arrieta, Greg Holland, J.D. Martinez, Carlos González, Carlos Gómez, Tony Watson and Eric Hosmer.

Hosmer was the only one who reached the expected total, receiving $144 million for eight years from the Padres. (Though released last season, San Diego still owes him nearly $26 million the next two years.) Six of those eight free agent received less years and notably less money than expected while González was only projected to earn a one-year deal; he re-signed with the Colorado Rockies for $5 million, more than half of what was predicted.

Moustakas’ case had a positive ending for such a worst-case scenario. The third baseman turned down a qualifying offer of $17.4 million from the Kansas City Royals following the 2017 season only to turn around and accept a one-year, $6.5 million deal from the cub that included $2.2 million in incentives on March 11. 

One year later in 2019, he settled with the Milwaukee Brewers on Feb. 19 for another one-year deal at $10 million. Eventually, Boras got his client $64 million for four years from the Cincinnati Reds, a franchise record for a free agent. Altogether, Moustakas was guaranteed $80.5 million for six years, a total not much less than the five-year, $85 million projected in his first time through free agency.

Going back and applying this alls-well-that-ends-well rationale to Boras’ others late-signing free agents doesn’t give him many new victories.

After sitting out through the first three months of 2014 and waiting to sign after the draft to remove the forfeiture of pick, Morales signed a two-year deal with the Kansas City Royals worth $17 million the offseason. His three-year, $33 million contract with the Toronto Blue Jays ahead of the 2017 season put his total free agent dollars at $57.4 million. He, like Moustakas, continued to perform at the plate, totaling 111 home runs and 395 RBI over those six seasons.

Drew, on the other hand, did not. After his initial turn at free agency, ended up receiving $11.5 million for three years. The shortstop had a 76 OPS+ and was worth 0.1 bWAR in those subsequent years following the 2014 hold out.

What Tricks Remain For Boras?

The only way out of this hole for Boras is for a team to acquiesce to his demands following a critical injury to their roster. How that happens can look markedly different.

At this point, the best outcome may take an injury to a key player for a team to bite the bullet and sign one of these top free agents. When Kendall Graveman required right shoulder surgery in January, Boras negotiated a five-year, $95 million deal with the Houston Astros for Josh Hader just a few days later.

A decade after Morales waited until after the amateur draft, there’s a reason no other player has opted for strategy. Though two versions of the CBA has not closed this loophole, there’s virtually no advantage to holding out that long. If any advantage did exist, it wields even less power today.

Back in 2014, the draft was held on June 5-7. This year, the Rule 4 First-Year Player Draft will be conducted on July 14-16, a full month later. Would teams really want to pay roughly $8 million (pro-rated to the qualifying offer of $20.325 million) to someone who hasn’t played in a professional game in over eight months when cheaper options could be available ahead of the trade deadline?

Which Teams Make The Most Sense?

Jorge Soler’s three-year deal with the San Francisco Giants seemingly takes them out of contention for adding another bat. His $42 million deal for three years places some potent pop in the middle of their lineup. However, if San Francisco want only their second season above .500 since the start of the 2017 season, they may need further backup.

Considering the Giants were contenders for signing Ohtani at $46 million per year and that they are still $28 million under last year’s payroll, they have to be favorites to sign one of the big four. The rotation could use another proven starter behind Logan Webb and third base is still a question mark with J.D. Davis and Wilmer Flores penciled in at the hot corner.

Could the Los Angeles Dodgers factor after already spending over $1 billion this offseason?

The payroll is already over $300 million, but it’s still $30 million shy of the New York Mets’ Opening Day roster from 2023. Chapman, who graduated from El Toro High School only an hour away from Dodger Stadium, would be a big upgrade defensively over Max Muncy at third base.

There’s been some ties between the Philadelphia Phillies and both Snell and Bellinger. Projected to have a $240 million payroll by Baseball Prospectus, the team is already at last year’s mark following the one-year, $8 million signing of Whit Merrifield. Talks of an extension with Zack Wheeler suggest the Phils couldn’t possibly bring him back and also add a new superstar. It’s likely one or the other, which is why Philadelphia shouldn’t be a factor.

The Toronto Blue Jays have already surpassed the 2023 franchise record by an additional $20 million. They, too, were contenders for Ohtani and may be willing to push their chips to the center of the table before Bo Bichette and Vlad Guerrero Jr. reach free agency following the 2025 campaign.

Even without making another move, the Chicago Cubs have the second-highest payroll in club history behind only the 2019 roster that entered Opening Day at $203 million, according to Baseball Prospectus. The rotation has some youthful options, but if the Cubbies run out of patience, expect another big transaction out of them.

Other clubs have also been linked to the Boras’ Four.

The Los Angeles Angels are in serious need of something positive to discuss. In the American League East, holes for the New York Yankees and — even more so — the Boston Red Sox suggest either club could acquiesce to Boras’ demands.

The Baltimore Orioles won that division last year with an Opening Day payroll of $60.8 million. Even by adding two of these players, they still might be outside the top 15 payrolls in the league.

If history teaches us anything about clients of Boras holding out past the start of Spring Training, it’s that these four players are more likely than not to be disappointed in what the future holds for them.