HOUSTON — The Alex Bregman sweepstakes started at 11:51 p.m. ET Wednesday when the Los Angeles Dodgers won the World Series to finish the first idle October of Bregman’s major-league career.
Bregman’s biggest priority when picking his next home is ensuring he does not experience another. Money and years will matter, but Bregman doesn’t project as the type of player who will tether himself to a tenuous situation solely for a larger salary.
“That’s something I want to do for my whole career is win,” Bregman told The Athletic in September. “That’s what I value the most coming up is winning.”
Whether the Houston Astros are equipped to do so is debatable. Across the next five days, the club can have Bregman’s undivided attention to state its case. A contract extension during this exclusive negotiating window seems unlikely, but Houston does have a chance to pitch its plans for confronting its looming crossroads.
Selling Bregman on plans for sustained success is imperative if the Astros are serious in their pursuit of a reunion. Jim Crane is fond of saying the championship window will remain open for however long he owns the club, but misallocated money, an aging roster, aversion to sizable free-agent deals and an abysmal farm system have thrust the promise into peril.
That Bregman has witnessed it all — and has an intimate understanding of the franchise’s standard operating procedures under Crane — makes the next five days far more consequential for third-year general manager Dana Brown. Contending next season is easy to envision, but anything beyond that will be more difficult to guarantee for Bregman, a player seeking a contract that covers at least the next six or seven years. Giving Bregman at least an initial blueprint of their plans should be Brown’s biggest task.
Brown already promised that “nothing is off the table” this winter while acknowledging the team “may have to get a little bit creative” during its most compelling offseason in recent memory. A franchise that’s long relied on its farm system to restock the major-league roster isn’t able to maintain that stance.
“It’s one of the weakest systems in the game: extremely thin, not a ton of quality depth and zero top-end talent,” said one opposing scout who has covered the Astros’ entire system. “They had some emergence of (Triple-A) guys this year unexpectedly, but those guys are complementary players at best and 4-A guys at worst. Difficult to see an everyday position player currently in the system and not sure there’s a big-league rotation piece either.”
That is just one rival evaluator’s opinion, though some versions of it have been echoed by members of the Astros’ organization throughout the past six months. Bregman has had a firsthand look at Houston’s diminished farm system for the past two seasons, be it in spring training or in-season call-ups. That the team had to pluck Ben Gamel, Héctor Neris and Jason Heyward off the waiver wire in August displayed its dearth of homegrown depth.
Houston’s farm system needed an overhaul when Crane hired Brown. Two years later, FanGraphs, Baseball America and MLB Pipeline all rank it either 29th or 30th in their organizational talent rankings. Trades for Justin Verlander and Yusei Kikuchi further diminished the system after Brown’s arrival, as did the lack of a first or second-round pick in 2021 or 2022.
The Astros habitually turn prospects unheralded by outside publications into productive major leaguers, but finding more top-end talent to comprise the team’s next core is mandatory.
Trading either Framber Valdez or Kyle Tucker before their final seasons of club control is the most straightforward way, but doing so would be a departure from anything the franchise has done during this golden era.
Perhaps Crane and Brown could lean more into free agency, but Houston just carried its highest payroll in club history — and crossed the luxury tax threshold. Whether Crane is prepared to do that again is a serious question. Signing Bregman to the sort of contract he wants would all but force it.
It isn’t in Crane’s nature to offer the sort of contract that would make Bregman or agent Scott Boras contemplate closing off overtures from 29 other clubs. Matt Chapman’s six-year, $151 million extension matches the longest contract Crane has ever given a player during his ownership tenure — and represents a floor for Bregman’s negotiations.
It would be out of character for Boras to allow one of his clients to bypass the open market, though two current Astros — Jose Altuve and Lance McCullers Jr. — are proof it can happen. Both players informed Boras they did not want to leave Houston. The agent obliged with the sort of contract extensions he often avoids.
Publicly, Bregman has made no such declaration. Following the Astros’ Wild Card Series loss against the Detroit Tigers, Bregman acknowledged he “hoped” to be back in Houston, but reminded a room full of reporters that “it’s free agency and I’ve never experienced that before. I’ll let (Boras) and all the teams handle that.”
Even if Crane and his baseball operations team offer Bregman the biggest contract in team history during the next five days — say, the five-year, $160 million deal offered to Carlos Correa during Houston’s exclusive negotiating window with him in 2021 — it would be illogical for Bregman and Boras not to see what other clubs are prepared to pay.
Many pursuing Bregman will have deeper pockets, dynamic minor-league systems and a clearer path to win for the duration of any contract they offer him. Sentimentality resides in Houston, but more sustainable plans for success could be elsewhere.
Perhaps during the next five days, the Astros can alter that imbalance.
(Top photo of Alex Bregman: Alex Slitz / Getty Images)
