This fall and winter will likely represent the biggest challenge in Chaim Bloom's tenure as chief baseball officer of the Red Sox.
As soon as the World Series concludes, it's widely assumed that Xander Bogaerts will choose to opt out of his contract and become a free agent. At the same time, third baseman Rafael Devers will be heading into his final season under the Red Sox' control.
How Bloom handles the two players will determine his legacy, and quite possibly his job security here.
It was one thing for Bloom to take the job in the fall of 2019, and months later, trade Mookie Betts. He inherited that mess and was effectively told to make the best deal he could in exchange for arguably the organization's best homegrown player in decades. Bloom couldn't be held responsible for the team's unsuccessful attempts to retain Devers; that dye had already been cast when Bloom was hired.
But Bogaerts and Devers will be different. Bloom will own whatever happens to the pair. To suggest that the team's initial outreach to the players were unsuccessful would be a gross understatement. The contract proposals served to alienate the players more than assuage them. The Red Sox effectively proposed to add one extra year at $30 million to Bogaerts' current contract, while using Atlanta's Matt Olson as a comparable player in their dealings with Devers -- despite the fact that Olson is three years older and doesn't play the same position.
As an organization, Bloom, team president Sam Kennedy and principal owner John Henry have said in interviews that the team would love to keep Bogaerts and Devers here for the remainder of their careers. But each time that goal is made public, invariably, the Red Sox manage to point out that the players have to want to remain, and that, given the amount of money at stake, well, you can't sign 'em all.
To which we offer, as a counterpoint, the Atlanta Braves.
The Braves play in a smaller market than Boston. They have the benefit of playing in a five-year-old ballpark, Truist Park, and the surrounding area, The Battery, has produced extraordinary revenue for the team. The Braves have a favorable TV deal, but their revenues pale in comparison to those of NESN, of which the Sox own 80 percent.
And yet, the Braves have done a remarkable job in securing their best under-30 players to long-term deals. In the last three years, president of baseball operations Alex Anthopoulos has extended:
* Ronald Acuna Jr. to an eight-year, $100 million (with two option years) deal in 2019 that locks up Acuna Jr. until at least 2026, and potentially through 2028.
* Ozzie Albies to a seven-year $35 million deal in 2019 through 2025, with two additional options years that could keep Albies under control though 2027.
* Matt Olson to an eight-year deal for $168 million, through 2029 with an option year for 2030 and
* Austin Riley to a 10-year deal for $212 million through the 2032 season, with an option year for 2033 season.
That's four foundational position players, each an All-Star, under the Braves' control through at least 2026, giving the Braves, at minimum, a five-year window with nearly half of their lineup secured for the entire time.
So, it can be done.
Some context is necessary here. The Braves are not infallible when it comes to getting their top targets signed. They famously were forced into dealing for Olson when they couldn't come to terms with their own homegrown star, Freddie Freeman. (Following a contentious winter-long negotiations, it's been alleged that Freeman's representatives never relayed the Braves' last, best offer, leading Freeman to instead sign with the Los Angeles Dodgers. The Braves then traded some prospects for Olson to serve as Freeman's replacement, then almost immediately signed him to an eight-year extension).
Moreover, the Braves have, to date, been unable to come to terms with their own shortstop, Dansby Swanson, who, for now, appears headed to free agency this fall, joining Bogaerrts, Trea Turner and likely, Carlos Correa for a magnificent shortstop class this winter.
Still, it's impossible to not be impressed with how the Braves have themselves up for both the near and far future. They identified Acuna Jr. and Albies early in their careers as players around whom to build and secured them to team-friendly deals that also manage to give both players security.
Then, they swapped out Freeman for Olson -- four years younger -- and, having watched Riley develop into one of the best overall players in the game last year, extended him, too.
Such a commitment isn't easy. It requires the proper evaluation of talent, a determination that the players in question are worthy of a long-term investment, and, not insignificantly, careful payroll management. The choices have to be smart -- pick the wrong player to extend, and your payroll will be saddled with dead money, and a top prospect can be blocked.
It requires the support of ownership, who, naturally, have to sign off on deals of this magnitude, and trust that Anthopoulos and his front office have made the right decisions. It means having a consistently competitive franchise, which convinces players that they can expect to contend for the life of the deal.
The Braves can make that guarantee for now. They've won the National League East in each of their last four seasons. They reached the NLCS two years ago, and are the defending world champions. It would surprise absolutely no one if they reached at least the NLCS again. And even with seemingly endless resources of Mets owners Steve Cohen, the Braves are poised to be factors in their division for years to come.
Again, the Braves haven't been perfect. There's still some emotional fallout to not getting a deal done with a franchise icon like Freeman, and the prospect of Swanson -- not homegrown, but a player who grew up in the area and wants to remain -- going elsewhere this offseason remains a possibility.
But to secure the long-term services of four foundational players in the last three years is an achievement not be dismissed lightly. And a reminder that with good planning and decision-making, a smart franchise can, in fact, hold onto its best players, pay them the market rate needed to retain them, and not bust its budget.
Imagine that.
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We wrote earlier this week about the precarious future for the Red Sox' starting rotation, given the uncertain futures for both Chris Sale and James Paxton, and the potential loss of Michael Wacha and Nathan Eovaldi to free agency.
At least, however, there are some internal pieces that could blossom, including Kutter Crawford, Brayan Bello and Bryan Mata.
The outfield picture, however, is even more suspect. In the current Red Sox outfield picture in the big leagues, Tommy Pham is eligible for free agency after the season, as is the injured Kike Hernandez. Jaylin Davis and Rob Refsnyder, while decent depth pieces, are career journeymen. Jarren Duran has become more suspect than prospect with a half-season to stake his claim on a future outfield spot.
Only Alex Verdugo, whom the Sox control through 2024, is guaranteed to return, and he's had a largely disappointing season even as he's been the victim of some bad luck when it comes to batted balls.
Worse, unlike with the starting rotation, there's little immediate help in the system. Recently, SoxProspects.com updated its prospect rankings and had just three outfielders in their Top 20 list. (Baseball America's list was similar). SoxProspects.com had Ceddanne Rafaela at No. 8, but Rafaela also plays some infield, including shortstop, and it's not definite that he projects as an everyday outfielder in the future.
Another Top 20 pick is Roman Anthony, who was the Sox' compensation pick for losing Eduardo Rodriguez in the recent draft. But as a player fresh out of high school, Anthony is probably four years away -- minimum -- from reaching the big leagues.
The best outfield prospect of all, meanwhile, is Miguel Bleis, who is ranked fifth (up from No. 8 in the previous ranking). Bleis is currently the talk of the Florida Complex League, where he's hitting .301/.352/.542 with 18 steals in 21 attempts, five homers and 21 RBI in 39 games.
Said one executive from a National League team: "We love him. He has the ability to really impact on both sides of the ball, with five-tool potential. Sounds like he's the best player (in the FCL).''
Another coach from an American League team compared his raw ability favorably to Rocco Baldelli -- before injuries derailed what many expected was going to result in an All-Star career.
Still another suggested that Bleis had both the athleticism and instincts comparable to All-Star center fielders.
It's important to note that evaluations can change. Two years ago, you might have heard similarly lofty projections for Gilberto Jimenez, who has tumbled from a Top 10 prospect to No. 29, and is struggling at High A, with a .699 OPS.
But there's a lot to like about Bleis, who at 18 and 6-foot-3 and 175 pounds, hasn't even completely filled out physically.
It will take a while for Bleis to complete his development and he'll be of no help in filling the vacancies this will exist in the outfield this winter. Still, he's certainly a player to remember, at a position where the Sox are currently thin.
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The last few years, the San Diego Padres have won the offseason and the trade deadlines. They've been praised for their willingness to be bold and do big things. Their payroll has skyrocketed, and fans have responded, filling beautiful Petco Park on many nights,
In the last two years, they've added, among others, Blake Snell, Sean Manaea, Josh Hader, Josh Bell, and of course, Juan Soto. They've outbid other teams -- when it comes to money and prospects -- to assemble one of the more talented rosters in the game.
And that influx of talent only added to the likes of Manny Machado and Fernando Tatis Jr.
Good for the Padres for that commitment, and to the aggressiveness of GM A.J. Preller, who also revealed that even as his club was concluding the mammoth deal to acquire Soto, perhaps the best hitter in the game, he was also trying -- unsuccessfully, as it turned out -- to pry Shohei Ohtani from the Angels.
But despite all the importing of talent, the Padres missed the 2021 playoffs, and currently sit 16 games back of the Los Angeles Dodgers in the National League West. They're now two games ahead of the Milwaukee Brewers for the third and final wild-card spot.
And this weekend, they're dealing with the fallout that Tatis, whom they made one of the richest players in the game's history (14 years, $340 million) after just 143 games in the big leagues, tested positive for PEDs, resulting in an 80-game suspension. Tatis, who was on a rehab assignment at the time, is banned for the rest of this season, the playoffs should the Padres qualify, and the first 41 games of next season.
Typically, team executives issue some sort of "we're-highly-disappointed-but-still-support-our-player'' statement after a PED bust. But Preller went much further, (rightfully) questioning Tatis's maturity and openly questioning whether he could be trusted. (Tatis also injured himself in an offseason motorcycle accident, then lied about it to the club).
Maybe the Padres will qualify for the postseason, and even without Tatis Jr., reach an NLCS meeting with the rival Dodgers or the Mets. Maybe there's a World Series in their near future -- there's certainly enough talent present.
But why do I get the feeling that the Padres' mad scramble to assemble one of the game's priciest rosters wasn't carefully thought out, and the Padres will never be as good as the sum of their many skilled parts?