Buster Posey Is Not Afraid

“What’s the biggest problem,” my Uncle George likes to ask. He takes a beat, leaving space for the question to be considered. “The same problem.”

A lifelong Yankees fan, Uncle George’s message seems to have been well received nonetheless by Red Sox chief baseball officer Craig Breslow.

Since signing third baseman Alex Bregman in February, Rafael Devers had been Breslow’s biggest problem. After a couple months of friction, the situation in Boston was handled in the exact way that Jack McKeon advised many GMs to resolve their problems decades ago: Get rid of the player.

Welcome to San Francisco, Raffy.

It will take some time — assuming he’s granted it — before we can thoroughly assess Breslow’s tenure overseeing baseball operations in Boston. But as we examined a few months ago, public perception doesn’t seem to concern him.

We can simplify the matter and look at it one of two ways: Breslow is a bold leader who does not care what others think about him, or Breslow is so arrogant and obtuse that he’s blind to the reality that a significant part of his job involves open communication and media relations. It’s risky business to hover around .500 in the standings and interpersonal skills.

Anyway we look at it, Rafael Devers is now playing for the San Francisco Giants.

I love Devers. It was love at first sight really, a one-way admiration that began in May 2015, when I saw him spray missiles around the now-demolished Municipal Stadium, where the Hagerstown Suns once played. I crossed paths with the Greenville Drive, the Red Sox A-ball affiliate, a couple times that summer. Devers hit everything. He had an advanced, seemingly preternatural feel for the barrel. He was balanced and controlled at the plate, used the entire field, and hit the ball hard from foul line to foul line. It was only Lo-A, but his bat was undeniable. At third base, he was adequate and showed signs of improvement.

In baseball, we’re always searching for “comps,” established or better-known players to compare younger players to. It’s a way of rounding out a scouting report. Comps add color to the picture a scout paints. It also may be quite flawed in the new age of information, where biomechanical measurements can yield a more precise encyclopedia of comparisons.

When it comes to trading a franchise player early into a decade-long contract, though, there’s only one comp: Giancarlo Stanton.

The Yankees acquired Stanton from the Marlins in December 2017, three years into his $325-million, 13-year deal. Miami — surprise, surprise — desperately wanted out of the remaining financial commitment, which was about $295 million. In a stroke of serendipity, the youngest prospect to head to Miami in the deal was a teenager named Jose Devers, cousin of Rafael.

Keeping it in the family, we know that the relationship between the player and the club had suffered significant damage in Boston. What I think we can surmise as well is that the Red Sox, like the Marlins, desperately wanted out from the long-term commitment to Devers.

What Have We Learned?

June is a strange time to think about the offseason and free agency, but the Devers trade underscores how averse so many teams are to long-term deals. In the last two years alone, free agents including Pete Alonso, Cody Bellinger, Alex Bregman, Matt Chapman, Jordan Montgomery, Blake Snell have struggled to find the security they would have found earlier this century. The prevailing opinion from baseball executives who have commented on the trade helps explain why.

Many of the reactions focus on the doomed nature of Devers’ contract. Some expressed surprise that the Red Sox were able to wriggle free from the obligation; in turn, they questioned the Giants for parting with a top prospect and taking on the entirety of the contract, which stands at more than $250 million over the next eight-plus years. Keep in mind, though, the Red Sox “freed” themselves of a player who was batting .274 with a .401 on-base percentage and a .505 slug. That type of production, regardless of price, doesn’t become available too often. Devers won’t turn 29 until late October.

Around Major League Baseball more recently, today isn’t as important as tomorrow. Prospect rankings, draft bonus pools, and financial flexibility suggest that style points are more important than wins. And yesterday?

Recent successes hold little value. I’m not even sure we’re asking “What have you done for me lately?” Instead, it’s “What might you be able to do in a couple years,” or '“What can’t you do in a few years?”

The Phillies, for example, have made the postseason each of the past three years — losing the World Series in 2022, losing in the NLCS in 2023, and losing in the NLDS in last season. In three years, Bryce Harper will be 35-years-old and making $26 million. Chances are his production in 2028 won’t be “worth” the money. The three ensuing seasons could be even worse. But that’s a short-sighted appraisal that ignores the entire body of work. The game can’t be World Series-or-bust for every team.

The Red Sox have achieved (greater) financial flexibility. But that measurement is a byproduct of strategy, not the end game. What’s next?

How, if at all, will Breslow and the Red Sox reallocate Devers’ salary? Keep in mind that Boston received pitcher Jordan Hicks as part of the trade. He’ll make $12M annually in 2026 and 2027, potentially dampening his team’s short-term enthusiasm for spending.

Part of the challenge with today’s game, especially when it comes to the free agent market and player valuation, is that so many of the teams and decision-makers think and behave so similarly. Posey is different.

Consider his challenge: Four years ago, Posey was in the midst of an All-Star season. He batted .304, reached base at a .390 clip, and slugged .499 (not too different from Devers’ current numbers).

He surprised almost everyone when he announced his retirement about a month after the season ended.

Three years after hanging ’em up, the 2012 NL MVP was named president of baseball operations for the Giants, replacing Farhan Zaidi, the executive with whom the organization and fanbase had become frustrated for his failure to sign impact free agents. For a team with money to spend, the narrative of winning on the margins became tired quickly. The franchise made a stark pivot.

In his first offseason, Posey signed free agent shortstop Willy Adames to a $182 million, seven-year deal, the largest contract ever inked by San Francisco. Now he has acquired Devers. (It’s safe to believe that Zaidi would not have acquired Devers under the same circumstances.) Posey has no interest in winning the balance sheet. He’s trying to course-correct an organization gone limp. Sustainability in San Francisco is better left to the city employees focusing on a climate action plan, renewable energy, and zero waste initiatives; Posey is focused on winning today.

On what had been just another day during the Winter Meetings of 2011, Kevin Towers broke the mid-afternoon chatter in the Diamondbacks’ suite. He wanted to address the assembled scouts, coaches, and executives. There was no PowerPoint, no visual aids, no spreadsheets. Just his words. Unbeknownst to us, a strategic planning retreat had occurred in KT’s mind over the several hours prior. He was ready to share:

One month earlier, Frank McCourt had agreed to sell the Dodgers. KT had it on good intel that the franchise was soon going to be purchased by Guggenheim Partners, a global investment firm with incredibly deep pockets. It might take the new group a year to realize their power, but it was coming. KT sensed that it was about to become significantly more difficult to compete; private equity was making its way into the NL West. As reigning division champs, he wanted to invest aggressively in the big league team before the new dawn in Los Angeles.

We examined many win-now maneuvers and made changes where we could, moving prospects for players who could help win games immediately. One of the most significant trades did not pan out as hoped (though the same could be said for Oakland). The D-backs acquired starting pitcher Trevor Cahill in a five-player deal with the A’s. For the sake of this story, it’s worth noting the other player who came to Arizona with Cahill: left-handed reliever Craig Breslow.

The Diamondbacks disappointed that season, but KT had correctly identified a rapidly closing window in the NL West. Guggenheim took control of the Dodgers in May 2012. It took them a year to get settled. Since then, the Dodgers have won the West every year but 2021, when a 107-win Giants team held off their 106-win rivals.

Posey faced those Dodgers as a player. He won a World Series title in 2012 while Magic Johnson and the freshly minted controlling partners were still finding their seats in Dodger Stadium. Posey and his teammates won another title in 2014, parlaying a Wild Card ticket into a Game 7 victory. He knows how opportunity comes and goes, how one move can positively impact a clubhouse and change the culture. Posey won’t be paralyzed by worst-case scenarios. He’s seeking advantages.

During their playing careers, Breslow and Posey faced each other three times.

On June 13, 2010, the Giants hosted the A’s. Breslow got Posey to pop up harmlessly. On May 12, 2012, in a game at Chase Field, Posey reached on an error by the D-backs third baseman. On June 11, 2017, with Breslow pitching for the Twins, Posey singled on a line drive to left field.

The common denominator in all three of those games is that Posey’s Giants won.

That’s what he’s returned to do again.