The Phillies' championship window may be bigger than we think. It's a problem.

Dave Dombrowski arrived in Philadelphia with a reputation.

First and foremost, he was a known winner. Dombrowski won a championship with Darren Daulton and the Marlins in 1997. He inherited a 43-win Tigers team in 2003 and helped put them in the World Series by 2006. And he won another title with Boston in 2018, after his Red Sox took the AL East for the third consecutive year.

Additionally, however, Dombrowski was known to go championship-or-bust, leaving organizations barren in his wake. Wrote PHLY contributor Jim Salisbury in December 2020, when the Phillies hired their new president of baseball operations: “Dombrowski is aggressive. When he smells a title, he goes for it, even if it means ripping apart a farm system and unloading prospects. Win the title and it’s worth it. Don’t win and you could be looking at some rough years down the road, as has happened in Detroit.”

It was a deal that long-frustrated Phillies fans would have happily made with Dombrowski: win now, suffer later. A decade-long postseason drought will do that to a fan base.

But something unexpected is going on.

Not only are the Phillies true World Series contenders right now, but they’re well-positioned for the future. Consider:

– The heart of the Phillies’ 2024 success is their starting pitching. Through the end of June, the rotation sports a sparkling 2.88 ERA, best in the majors.

And the pitchers responsible for that number should be together for a long time: Aaron Nola signed a seven-year deal with the Phils this past offseason, locking him up through 2030. In March, Zack Wheeler signed a contract extension through 2027. The team recently signed a deal with Cristopher Sanchez that could keep him in the fold through 2030, and they’re rumored to be working on something similar with Ranger Suarez (who won’t reach free agency until 2026 even without a new deal).

Wheeler, Suarez, Nola, Sanchez. If they’re not four aces, they’re something close. With talented starting pitching in short supply across Major League Baseball, the rotation alone should keep the Phillies in the postseason mix next year and beyond.

– Dombrowski and his team have completely revamped a Phillies bullpen that posted a staggering 7.06 ERA in the 2020 season. This year, Phillies relievers are sporting a 3.34 ERA, good for top-five in the majors.

Relievers typically do not get long-term contracts. But Jose Alvarado and Matt Strahm, two key cogs in the Phillies machine, won’t reach free agency until at least 2027. Seranthony Dominguez and Gregory Soto will be Phillies until at least 2026. Orion Kerkering and other young bullpen arms, meanwhile, will be under team control about as long as Nola.

The Phils have come a long way since the Brandon Workman/Heath Hembree era, and it’s a solid bet that the bullpen will be a strength for at least a few more years.

– The infield is anchored by two perennial MVP candidates: Bryce Harper at first base and Trea Turner at shortstop. Harper is under contract through 2031 and Turner inked a deal that takes him through 2033. Alec Bohm, currently leading the National League in All-Star voting among third basemen, won’t reach free agency until at least 2027. Same goes for super-utility man Edmundo Sosa. And Bryson Stott will be under team control until 2028.

J.T. Realmuto is the infielder that will become eligible for free agency the earliest, in 2026. But Realmuto will turn 35 before the ’26 season starts and has logged a ton of innings. The timing on his contract might be ideal from the team’s perspective.

– In the outfield, Brandon Marsh and Cristian Pache are under team control until 2028. Johan Rojas will be a Phillie into the 2030s if the organization wants him to be. Nick Castellanos is here through 2026.

– Designated hitter Kyle Schwarber is under contract through 2025.

In short- If you like your Phillies team, you can keep your Phillies team. With Dombrowski at the helm, the organization has locked in the core players currently responsible for the best record in baseball.

But the best part? The farm system has improved while the Phillies made deep playoff runs over the past couple years.

In 2021, pitcher Spencer Howard was widely regarded as the Phillies’ top prospect. Howard, now with the San Francisco Giants organization, has a 6.93 career ERA in 45 major league games.

Here in 2024, the Phillies’ top prospect is pitcher Andrew Painter. Painter was set to compete for a job in the Phils’ big-league rotation as a teenager in 2023, after being named MLB Pipeline Pitching Prospect of the Year in ’22. The 6’7″ righthander is currently recovering from Tommy John surgery, but should pick up where he left off in 2025. If he lives up to expectations, the Phillies will add a front-line starting pitcher for next to nothing in terms of payroll.

Behind Painter there’s more talent. SS/3B Aidan Miller is a highly regarded power bat that could reach the majors around the time Bohm looks for a big payday. Speedy outfielder Justin Crawford is opening eyes. RHP Mick Abel and SS Starlyn Caba round out the Phils’ top five prospects in most rankings.

Dombrowski and the Phillies now face a happy dilemma. Do they trade some prospects to bolster one of the most talented Phils squads in the 142-year history of the franchise? Or do they forego major changes and ride out a window of contention that could stretch for years?

It’s an incredible problem to have. This year’s Philies have allowed the fewest runs in baseball and scored the fourth-most. They’ve weathered injuries to Trea Turner, Brandon Marsh, and J.T. Realmuto without missing a beat. They appear to have dodged bullets on injuries to Bryce Harper and Kyle Schwarber, with each star expected to return around the all-star break. They’re on pace to win 106 regular season games, which would shatter the team record of 102.

After coming tantalizingly close to a championship in 2022 and 2023, it feels like a good time for the organization to go all-in. Maybe Dombrowski smells that title and is ready to go for it, the Aidan Millers of the world be damned.

But there’s a strong counterargument to that approach.

– First, it’s unclear whether there are players available who would meaningfully move the needle on the Phils’ championship odds. The expanded MLB playoff format keeps most of the league in some level of contention for a title. Teams looking to buy help at the July 30 trade deadline will face a true sellers’ market. It’s not crazy to think that a trade package for White Sox outfielder Louis Robert Jr. would have to include Painter, Miller, or even both.

No prospect should ever be considered truly “untouchable.” Everyone has a price. But when expectations for the Phils’ top prospects are so high, it’s dicey to move them for a player with some question marks. Robert Jr. hit 38 home runs in 2023 while slashing .264/.315/.542 (.857 OPS). But he has battled a variety of injuries and the ’23 season marks the only year he ever played in 100 games or more. Robert Jr. even missed the beginning of the ’24 season, and he’s currently hitting .206 through 29 games.

Then again, he does have 8 home runs in those 29 games. A Gold Glove winner in 2020, the 26-year-old sure would look good in the Phillies outfield. But…

– Second, even if the Phillies make moves to establish themselves as the favorites to win the World Series this year, they will still be heavy underdogs to the field. As of Sunday night, the Phils are third in Vegas odds to win it all, with implied odds of 17.2%. That’s close to the second-ranked Yankees (17.5%), and within shouting distance of the top-ranked Dodgers (25.0%).

No matter how good a team is, MLB’s 12-team postseason ensures that one squad will never be favored over the field. Luck also plays a huge part, of course. Would it make more sense for the Phillies to sit tight and take a 15-20% shot at a title each year for the next several years?

Decisions, decisions…

Making the right call could cement Dombrowski’s legacy as one of the greatest baseball executives of all time. The Phillies could win one (or more!) championships and the president of baseball operations would be forever loved in the Delaware Valley.

Making the wrong call could alter the trajectory of a franchise that finally seems to have figured out how to operate. The Phils may fall just one player short in the 2024 World Series. Or they may watch from the NL East basement as Painter and Miller lead teams to multiple championships.

No pressure, Dave. Just get it right.

Follow PHLY Phillies writer John Foley on twitter here.