Red Sox can relate to Astros reasons for not signing free-agent Jackie Bradley Jr.

BOSTON, MA - SEPTEMBER 10: Jackie Bradley Jr. #19 of the Boston Red Sox throws the ball during the fifth inning of a game against the Tampa Bay Rays on September 10, 2017 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)
BOSTON, MA - SEPTEMBER 10: Jackie Bradley Jr. #19 of the Boston Red Sox throws the ball during the fifth inning of a game against the Tampa Bay Rays on September 10, 2017 at Fenway Park in Boston, Massachusetts. (Photo by Billie Weiss/Boston Red Sox/Getty Images)

Red Sox and Astros are passing on Jackie Bradley Jr. for similar reasons

Jackie Bradley Jr. is arguably the best position player that still remains on the free-agent market. That the former Boston Red Sox center fielder is still searching for a new home as players report to camp for spring training isn’t a testament to his perceived value. The challenge that Bradley Jr. faces is that the teams expected to be the strongest suitors for his services appear content to move on without him.

The Houston Astros were initially expected to push hard for Bradley Jr. as the replacement for George Springer, who signed a lucrative free-agent deal with the Toronto Blue Jays, only for their interest to fade over the winter. Houston seemed like a perfect fit for Bradley Jr. when the offseason opened. What changed?

According to Ken Rosenthal of The Athletic, Houston’s desire to remain under the $210 million luxury tax threshold is deterring them from signing Bradley Jr. Their payroll currently sits at around $201.3 million, per FanGraphs, leaving enough wiggle room for mid-season moves but not enough to squeeze in Bradley Jr. at anything close to his asking price.

As Rosenthal explains, it’s not the financial penalty for dipping into tax territory that worries the Astros. The team is more concerned with the diminished draft-pick compensation that would come as the result of paying the tax.

The Astros are facing a pivotal offseason next year with shortstop Carlos Correa hitting the free-agent market, along with starting pitchers Justin Verlander and Zack Greinke. Houston probably can’t afford to keep all of them but they can recoup a draft pick if any of those players decline a qualifying offer before signing elsewhere. That compensation pick would be granted after the second round but falls to after the fourth round for tax-paying teams.

Losing any of those players to free agency would clear some room in the budget to spend on alternative options but the choices could be limited to those who didn’t receive a qualifying offer if they cross the tax threshold in 2021. The penalty then would be their second- and fifth-highest picks and a $1 million reduction in their international bonus pool, as opposed to only a second-rounder and $500,000 reduction if they stayed under.

The draft pick and bonus pool penalties are a steep price to pay, especially for an Astros team that lost their first- and second-round picks in 2020 and 2021 as part of the penalty for the sign-stealing scandal.

The Red Sox face a similar dilemma with a payroll of approximately $207.5 for luxury tax purposes. Chief Baseball Officer Chaim Bloom has stayed in touch with Bradley Jr. while monitoring his free-agency situation but there’s no realistic way to fit his salary into their budget unless they find a way to cut payroll elsewhere.

Crossing the tax line has consequences that the Red Sox should be cautious of for the same reasons Houston intends to stay under. Boston already lost a second-round pick in last year’s draft for their own sign-stealing transgressions. That’s not nearly as tough as the punishment the Astros were hit with but it still leaves the Red Sox more sensitive than most teams to the concept of draft pick penalties.

Eduardo Rodriguez is entering his final season of club control so unless the Red Sox are able to hammer out an extension, the lefty will test free agency for the first time next winter.  J.D. Martinez could join him on the open market if he declines the player option on the final year of his contract. Unless this year goes horribly wrong for these players, the Red Sox would presumably extend a qualifying offer that could soften the blow of losing them to free agency. That compensation would less appealing if Boston were to be penalized for exceeding the tax.

If Rodriguez signs with another team, Boston will need to replace him and the market could produce several appealing options, including Max Scherzer, Clayton Kershaw, Noah Syndergaard, Marcus Stroman, and Corey Kluber. Trevor Bauer could jump back into free agency again if he declines his player option. The pair of aces in Houston have some age and injury concerns but both could conceivably be considered in this group. The Red Sox might want to consider some of those names even if they are able to keep Rodriguez.

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Boston could be looking for another bat next winter to upgrade the outfield or replace Martinez in the DH role. Charlie Blackmon, Nick Castellanos, Michael Conforto, and Kris Bryant could be available. Maybe the Red Sox move Rafael Devers to the DH spot and Bobby Dalbec over to the hot corner. Freddie Freeman and Anthony Rizzo would be appealing if a need at first base suddenly opened up. The Red Sox don’t need a shortstop but given the star talent that next year’s free-agent class could offer at the position, they might want to consider targeting one of them and figure out how they’ll fit with Xander Bogaerts later.

The problem is that if these players have successful 2021 seasons, they will almost certainly be extended a qualifying offer. If Boston pays the tax this year, it means a harsher penalty awaits if they chase one of these enticing free-agents next offseason.

Bloom has made significant strides toward replenishing the barren Red Sox farm system and he’s unlikely to let that process stall by diminishing his collection of draft picks or limiting what he can spend on the international market.

The decision to slash payroll to dip under the luxury tax last year was met with frustration and many fans are still wondering why the team isn’t blowing beyond the threshold now that the penalties have been reset. The reasons are very clear and it’s not just about the money. John Henry’s wallet can handle a tax bill. The narrative that the franchise is run by cheapskate owners and a front office intent on turning the Red Sox into the low-budget Rays is misguided and woefully ignorant. Exceeding the tax has other consequences that the Red Sox aren’t in a position to sacrifice.

The Red Sox and Astros both reside in solid markets that can support a high payroll. They each have a recent championship under their belt and are poised to contend again in the near future yet neither is close enough in 2021 to risk paying the luxury tax. Bradley Jr. is an excellent defensive player with plenty of playoff experience. He can certainly help a contending team but he’s not the guy who would put either of these clubs over the top and that’s why they are pivoting in other directions.

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