At a competitive crossroads, the Houston Astros began an overhaul Monday, letting go of fourth-year general manager Dana Brown amid a season where the team is tied for first place in its division but approaching September with a losing record.

Manager Joe Espada, promoted by Brown following the 2024 season, remains in his position for the time being. He left the team, which entered Monday at 65-66, early Sunday to attend to personal matters. Both Brown and Espada entered this season in the final year of their respective contracts.

Owner Jim Crane’s decision to move on from Brown, who was in the final year of his contract, prompts a plethora of questions for a 72-year-old who has reiterated that “while I’m here, the window will always be open.”

Nothing about the past two seasons under Brown and Espada has suggested as much. The Astros, who were 330-285 in Brown’s three-plus seasons leading the franchise, ended their eight-year streak of playoff appearances in 2025. Houston’s depth on both the 26-man roster and within the upper minor leagues has narrowed to near nonexistence, applying pressure on an aging core to keep a championship pedigree intact.

That Brown could not replenish the organization’s depth will be remembered as his downfall. A straight-shooting scout with extensive experience in player evaluation, Brown, 59, had never run a baseball operations department before Crane hired him away from the Atlanta Braves, where he spent four seasons as a special assistant to general manager Alex Anthopoulos.

All of Brown’s baseball experience came in talent evaluation during stops with the Pittsburgh Pirates, Washington Nationals, Montreal Expos and Toronto Blue Jays. That background appealed to Crane, who hoped Brown could rejuvenate a fallow farm system while still constructing a championship roster at the major-league level.

Now Crane has turned over duties to assistant GMs Charles Cook, Gavin Dickey and Connor Huff, as well as to senior adviser Jeff Bagwell, whose influence in baseball operations decisions cannot be overstated. According to a news release, Crane will oversee all baseball operations decisions “through the transition period.”

In a statement, Crane thanked Brown for leading “our baseball front office through key scouting, draft and development efforts.” Brown said in the same release that he wishes the organization well and plans to continue his 36-year career in baseball.

Upon his arrival in Houston in January 2023, Brown promised a plethora of contract extensions for young players — similar to the model Anthopoulos used with the Braves — while asking Crane and fans to “buckle up” in preparation for a bevy of moves.

Instead, Brown consummated two extensions: one for pitcher Cristian Javier in 2023 and another for franchise cornerstone Jose Altuve in 2024. Javier underwent Tommy John surgery one year after signing the five-year, $64 million pact and has spent most of the 2026 season on the injured list.

Brown’s failure to extend ace pitcher Hunter Brown — who expressed interest in a deal before the 2024 season — and All-Star shortstop Jeremy Peña are among his biggest missteps. The team’s inability to extend Kyle Tucker prompted Brown to trade the homegrown outfielder to the Chicago Cubs in 2025 in a deal that has since aged well — but nowhere near enough to overcome some of Brown’s other missteps.

How much of the dysfunction can be attributed to Brown, who took over after the departure of GM James Click following the Astros’ 2022 World Series championship, may be a matter of interpretation. Brown inherited the awful contracts Crane gave to first baseman José Abreu and reliever Rafael Montero while acting as the team’s head of baseball operations. Brown rid the roster of both players, but for a team operating with self-imposed financial restrictions, those salaries became albatrosses even in their absences.

Crane’s aversion to long-term deals, along with some of his spending habits, can’t be overlooked. Crane has still never guaranteed a player more than $151 million and, until two years ago, had never given a free-agent deal worth more than $58.5 million.

Before the 2025 season, Brown signed closer Josh Hader to shatter that precedent. The five-year, $95 million free-agent pact is the largest Crane has ever authorized, one during which Hader has accrued 5.1 wins above replacement, according to Baseball-Reference.

Some of Brown’s other major-league additions were more suspect. Japanese right-hander Tatsuya Imai was recently demoted to the bullpen amid a miserable first season after receiving a three-year, $54 million deal from Brown in the offseason. Crane had involvement in that contract, as did the team’s partnership with Daikin, the Japanese HVAC company that now has naming rights on the team’s ballpark.

Imai is one of six pitchers Brown added to the major-league roster in the offseason. Three of them — Roddery Muñoz, Ryan Weiss and Nate Pearson — have been designated for assignment. Two others, Mike Burrows and Tatsuya Imai, were yanked from Houston’s starting rotation.

Only one of them, swingman Kai-Wei Teng, has fulfilled expectations within a pitching staff that is one of the worst in baseball. Together, the six managed a 5.51 ERA — all but sealing Brown’s fate during a make-or-break season.