It’s not just buyers and sellers. Here’s the winning window every team should target

Live through enough baseball seasons, and they start to feel like family vacations from a ’90s sitcom. In the winter, plans take shape and balloon into grand, hopeful designs. In the spring, everyone piles in to hit the road and make it happen. By the time the MLB trade deadline arrives in the sweltering summer — Aug. 1 this year — the misty visions of perfection have shriveled into uncertainty for most. It’s time to get realistic, time to pull over, ask for directions and accept a less dreamy version of the trip at hand.

As Hannah Keyser argued here at Yahoo Sports, contemporary front offices are, if anything, too good at avoiding the pitfalls of exuberance. Rather than teams openly “going for it,” it’s far more common to hear about sustainability or maintaining a steady core to compete year in and year out, concepts often trotted out to explain why a more thrilling, more immediate move wasn’t made.

The logic behind that shift, unfortunately, is sound. It’s less entertaining to think of a team’s best move in an accountant-speak array of probabilities, but baseball’s postseason stokes more randomness than other sports’ and, therefore, provides less incentive for already good teams to shoot for the moon.

Like a lot of post-Moneyball baseball trends, though, the general rule has perhaps been accepted too readily and too widely. Lots of general managers are correct in believing that collecting eggs for this season’s basket would ultimately diminish their chances of winning a World Series, any World Series. And yet someone, as Keyser points out, is making their very best run at it right now. Some handful of teams would likely benefit from piling resources into the 2023 stretch run instead of holding them in reserve for a future contender that might never arrive.

But who? That’s the trick. With less than two weeks until the trade deadline, let’s go beyond buyers and sellers. The exercise here is to place every team into a tier based on its winning window — when their wins appear to matter most, where they should set their sights as they deal their way through the summer heat.

Now: Chase that 2023 glory

Tampa Bay Rays

Texas Rangers

These teams should be good in 2024, in 2025, and so on and so for — look out! That is exactly the trap we’re trying to avoid.

The Tampa Bay Rays are routinely praised for maintaining a perpetual-motion machine of a roster that is also almost perpetually good. They have reached the World Series recently, and with Wander Franco signed long-term, there’s good reason to believe they will be a threat for a long time.

Will there be many seasons with this clear a path, though? FanGraphs currently gives the Rays an 11.1% chance of winning the World Series, tops in the American League and third in MLB. The temptation is to see every first-half development — Yandy Díaz hits for power! Isaac Paredes is a star! — as an established, persisting fact. Or to take this year’s positioning and think, “Wait ‘til they have all this plus a healthier pitching staff.” But that’s just not how it works. Jeffrey Springs is hurt this year; someone else will likely be missing in 2025.

You can apply a lot of the same logic to the Rangers, who have tremendous success stories this season that can’t be counted on to sustain for very long. Both teams also have crucial positioning to fight for. The Rays just dropped out of first place in the AL East. The Rangers will have to fend off the Astros until the very end. They’ll need every edge they can find.

These are teams good enough to win the World Series. No, the specter of randomness cannot be avoided, but this year might be their very best shot.

Los Angeles Dodgers

Philadelphia Phillies

For the Dodgers and Phillies, it’s less a matter of fielding the best version of themselves this season and more about being close enough and old enough to push the pedal to the metal.

The Dodgers, in particular, are overwhelmingly powered by 30-year-old Mookie Betts, 33-year-old Freddie Freeman and outstanding catcher Will Smith, who 2.5 years from free agency. In the starting rotation, Clayton Kershaw considers retiring every offseason, and Julio Urías will hit the market this winter. L.A.’s next wave of talent hasn’t quite popped yet. It’s the Dodgers, so the young players will probably figure it out, but the lack of surefire continuity raises the stakes on 2023.

Miami Marlins

Milwaukee Brewers

Toronto Blue Jays

These teams are close enough to make a run in 2023 while being far enough from solid footing (or divisional supremacy) in 2024 and beyond to think the grass might not get any greener.

Now but also later: The hedged bets

Atlanta Braves

The Braves are sort of their own category. The best team in baseball has seven of its eight best players signed until kingdom come. Atlanta should absolutely be going for it in 2023, but its biggest concern is the bullpen, which is the cheapest in-season need to address, and any accounting of this team simply has to note that the Braves are already set up to win in every foreseeable future season. They won’t be swapping out any members of their core in the next two weeks.

Baltimore Orioles

Arizona Diamondbacks

Cincinnati Reds

San Francisco Giants

This is the rosiest, most optimal version of baseball’s most common trade-deadline stance. Bolstered by young talent, with more on the way, these teams are contending in 2023 but still playing with house money. They will make additions but not at any great expense to the group of key players likely to keep them in the conversation in 2024 and ’25. Even to the most cynical among us, Adley Rutschman, Corbin Carroll, Elly De La Cruz & Co. don’t look like one-trick ponies.

Houston Astros

Boston Red Sox

Minnesota Twins

Cleveland Guardians

In practice, these teams should exhibit the same sort of restrained ambition. It’s just going to feel a lot worse. Where the Orioles and Diamondbacks have their fans in the throes of puppy love, of gauzy, honeymoon-stage bliss, these teams are starting to show beige flags. They are good enough (or in a bad enough division) to add, but they might pause before doing so.

Currently in the postseason picture or too close to cut the engines, the Astros and Red Sox are having the sort of seasons that would feel better if their trajectories were different, if their divisions didn’t have fresher faces beaming toward October. The Red Sox, in particular, are on the periphery of this season’s race, but they have enough promise bubbling up through the farm system that they might consider a needle-threading “buy and sell” deadline in which they flip Adam Duvall or James Paxton for younger, major-league-ready pieces.

The Twins and Guardians could feasibly be placed a tier up, alongside the Brewers, but you can’t watch them and envision success against any real contenders who have to test their mettle against better divisions.

New York Yankees

Firing hitting coach Dillon Lawson, getting Carlos Rodón back and demolishing fans hasn’t worked. The only thing the Yankees seem capable of doing right now is waiting for Aaron Judge to return from his toe injury. In the meantime, they are swooning toward needing to prioritize 2024. Even at 50-47, their playoff odds in the bombastic AL East (28%) are virtually even with those of the 46-51 San Diego Padres. GM Brian Cashman’s roster is stuffed with the aged and the injured, sprinkled with burgeoning talents not yet ready to carry the load. Any club with Judge and Gerrit Cole could muscle its way to the promised land, but this increasingly looks like a team in need of a page-turning transition, not mere reinforcements.

2024: Actually wait ‘til next year

New York Mets

San Diego Padres

St. Louis Cardinals

Expensive teams that fall flat lead to baseball’s favorite form of catastrophizing. Do the Mets and Padres need to blow it up? Should San Diego trade Juan Soto? No, these teams are having a rough time in 2023, but they have enough talent (and eager ownership cash) on hand to pursue brighter days in 2024. What they can do now is flip players on expiring contracts — of which all these clubs have several — to bolster a more urgent run next season, when Soto, Max Scherzer, Justin Verlander, Pete Alonso and Paul Goldschmidt will or could be in the final guaranteed years of their contracts.

Seattle Mariners

The Mariners are here not because they need to retool for 2024 specifically but because they have very few apparent options other than to run it back. Their tremendous pitching staff boasts a bunch of guys locked in for the long-term — Luis Castillo, Logan Gilbert and George Kirby, plus several intriguing rookies — while their lineup is punchless, suffering from a lack of depth, veterans who dropped off a cliff and Julio Rodríguez’s sophomore slump. The Mariners aren’t likely to move Castillo, Gilbert or Kirby, and they definitely aren’t moving Rodríguez, so it might be a matter of flipping a relief pitcher or two and perhaps impending free agent Teoscar Hernández to find some new potential offensive contributors.

2025: The approaching future

Los Angeles Angels

Chicago Cubs

This is probably a darker view of these two fringe contenders and deadline pivot points than their front offices or fan bases would put forth. The Angels have a well-documented, Shohei Ohtani-shaped quandary on their hands. Their chances of achieving the impossible dream (making the playoffs with Ohtani and Mike Trout) are better than they were a week ago, thanks to the Yankees, but still vanishingly slim. They might make a go at it anyway, but Ohtani trade or not, this organization will likely need to regroup around Logan O’Hoppe, Zach Neto and a round of future-focused swaps to try to deliver something before Trout tips into steeper decline.

The Cubs are a more complicated case. They could squint and see themselves in the NL Central catbird’s seat, but if it didn’t happen this year with Marcus Stroman and Cody Bellinger — two of the trade deadline’s best potential rentals — what exactly portends success in 2024? Dansby Swanson has played well, and late-blooming starter Justin Steele looks like he might actually be a No. 1 or No. 2 type, but once the Cubs trade Stroman and Bellinger, their second-best starting pitcher is Kyle Hendricks (33 and throwing 87), and their second-best position player is Nico Hoerner, who is valuable on defense and the bases but nonetheless runs a below-average batting line. The Cubs have an opportunity to boost their future standing at this deadline. The question is whether they need to push their expectations back a bit to raise their ceiling.

Pittsburgh Pirates

Washington Nationals

These teams are rebuilding but can begin to put target dates on the prospects they fetch for veterans. The Pirates showed flashes this year and might even envision themselves as 2024 contenders, but 2025 would not be a failure for a team that just summoned No. 1 overall draft pick Henry Davis and continues to give a bounty of other prospects MLB playing time to figure out their games.

The Nationals, on the other hand, might find 2025 a bit aggressive. Still, many of the players who came back when they sold off their 2019 core are already contributing in the majors — CJ Abrams, in particular, has made serious strides, batting .352 over the past month. The biggest young piece, literally and figuratively, is outfielder James Wood. The 6-foot-6 outfield prospect who joined in the Juan Soto trade is tracking toward a 2024 debut, and No. 2 overall pick Dylan Crews might not be far behind, which means 2025 should be viewed as go time in Washington.

2026 or beyond: The indeterminate future

Chicago White Sox

Detroit Tigers

Colorado Rockies

Kansas City Royals

Oakland Athletics

The White Sox do not seem inclined to blow it up this summer or even this winter, but things are looking bleak on the South Side. Injuries, ineffectiveness and generally jumbled roster construction have torpedoed a once-exciting core. Building around Yoán Moncada, Eloy Jiménez, Andrew Vaughn and Tim Anderson doesn’t look like a worthwhile plan anymore, unless the plan is to slug your way out of being the worst defensive team in baseball … for the 60 games a season in which the core is mostly healthy.

That leaves Luis Robert Jr. — having a phenomenal, career year in one of his first healthy seasons — and Dylan Cease — one year removed from his career year. They are both signed through 2025 (plus two club options, in Robert’s case), and it is getting harder to foresee a contender springing up around them, even in the AL Central. Unless the White Sox plan to blow the doors off their longstanding spending habits, they might be better off taking the plunge while Robert and Cease are at their most appealing.

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