Here’s Who Will Win the Next Five World Series

Pending a healthy return, Corey Seager will resume his role at the heart of the Dodgers’ roster.
(Photo: Arturo Pardavila III)

On a recent podcast episode, Eric Longenhangen and I discussed the premise for this article, which is another way of asking which organizations are healthiest in the short-to-medium term. The factor that goes furthest towards answering that question is present on-field talent, although salary, controlled years, the presence of impact minor leaguers on the horizon, and front-office quality are all relevant — as is payroll ceiling, which serves as a proxy for margin for error. With the World Series starting tonight, it seemed like the right time to look ahead at the favorites for the five World Series beyond this one.

I’ve experimented with some objective ways of measuring organizational health. I think it’s ultimately possible to produce an algorithm that would do a solid job, ranking teams objectively in a number of key categories. It would also require considerable time. Eager to arrive at some kind of answer, I’ve settled for subjective assessment for this version of the post, but I intend to work on something more systematic in the winter.

Here are the criteria I’ve considered to produce these rankings: short-term MLB talent, long-term MLB talent/upper-minors prospects, lower-minors prospects/trade capital, payroll ceiling, MLB coaching/front office, and amateur signings (draft and international). You could quibble and combine or separate a few of those groupings, or argue some of these can’t be quantified properly. You may be right, but we’ll keep tweaking things until they are.

I had originally intended to limit this list to five teams for purposes of symmetry, but the top tier looked like seven teams to me, and the sources by whom I ran this list agreed. In the same way that the I approached the Trade Value Rankings from the point of view of a medium-payroll, medium-term-focused team, I’ve undertook this exercise by asking which team would be most attractive to a prospect GM if his or her only interest is to win the most World Series possible (and not have low state income tax, run a childhood team, or live in a cool city) over the next five seasons.

Without further explanation, here are the organizations most likely to win the 2019-23 World Series.

1. Los Angeles Dodgers

The top-three teams on this list all have some reasonable claim to the top spot, but I ultimately went with the Dodgers, as they have a little more certainty in terms of on-field personnel than the Yankees possess, while both clubs feature similar built-in financial advantages. (Houston lags behind on the second count.)

Brian Dozier, David Freese, Yasmani Grandal, Manny Machado, Ryan Madson, Hyun-Jin Ryu, and possibly Clayton Kershaw are all becoming free agents after the World Series. That should worry Dodgers fans a bit. But Los Angeles also has a better farm than the Yankees, a slightly easier league, and a clearly easier division, along with reinforcements on the way. The Dodgers have two of the top three catching prospects in the game waiting in the upper levels (Keibert Ruiz and Will Smith), an MVP-candidate shortstop returning from Tommy John surgery (Corey Seager), another top hitting prospect who’s big-league ready (Alex Verdugo), plus the money to bring Kershaw back and still afford upgrades at a spot or two.

The flexibility afforded by Cody Bellinger’s defensive flexibility, plus the presence of multi-positional dynamos like Enrique Hernández and Chris Taylor — along with an established bullpen ace in Kenley Jansen and an emerging starting ace in Walker Buehler — all gives the Dodgers the short-to-medium-term personnel edge to take the top spot.

2. Houston Astros

I was prepared to put the Astros behind the Yankees, since the Bombers’ financial edge and superior scouting/development make up for the deficit in short-term talent. That said, the Yankees are forced to contend with the Red Sox, which should produce something like a 50/50 split over the next five years between division titles and Wild Card appearances. On the other hand, the Astros don’t have a clear, consistent second power in their division. A 90-something-win season is about standard for teams like this, and there’s a real chance the Yankees never get to the ALDS with that win total, while the Astros are far more likely to have home-field advantage guaranteed in a playoff series. For that reason alone, the Astros slide just ahead of the Yankees.

The pending free-agent class includes Dallas Keuchel and Charlie Morton, though the top pitching prospect in baseball (Forrest Whitley) is ready to fill in for one of those next year. Marwin Gonzalez is a pending free agent, but his corner-outfield spot is ready to be filled by another top-10 prospect in the game, RF Kyle Tucker. The core is still solid and locked up for long enough that the payroll deficit with the Yankees shouldn’t be a huge worry in the short-term, but likely will be toward the end of the five-year window I’ve defined here.

3. New York Yankees

Eric and I often talk about the Yankees in glowing terms when it comes to their process and outcomes, particularly in the amateur markets. They are generally regarded to be top-five (if not better) in terms of developing their minor leaguers and signing/drafting players in the draft and international markets. This allows them to continue to turn small investments into tradable assets — and GM Brian Cashman has been aggressive in trading multiple middle- to lower-tier prospects for short-term help, trusting that this machine will backfill the openings.

There are some questions surrounding the big-league team, however. There isn’t a clear long-term answer at first base; it isn’t obvious that Gary Sanchez will be a catcher for as long as some Yankee fans originally hoped; they’re now short an infielder for at least the first half of 2019 after Didi Gregorius’s elbow surgery; Miguel Andujar’s defense was historically bad this year; and the rotation needs to be bolstered. The farm system isn’t positioned to address those holes, but the Yankees have a good recent track record of solving such problems and also won’t have the constraints of the luxury tax about which to worry this offseason.

The club has a number of pending free agents, but not many current impact-type guys, with David Robertson representing possibly the best. Others include Zach Britton, J.A. Happ, Lance Lynn, Andrew McCutchen. Much of the departures come from the bullpen, the strength of the team.

The Astros and Red Sox will remain in direct competition with the Yankees for at least the next few years, while Cleveland and Tampa Bay aren’t going away, either. They also don’t have George Steinbrenner in charge of the checkbook, so the spending likely won’t go out of control anytime soon, but the Yankees are still set up for a good run over the next five years due to a core with tons of controllable years.

4. Cleveland Indians

The Indians are the clear heavyweight in the weakest division in baseball, and they employ the top two players from our recent Trade Value Rankings in Francisco Lindor and Jose Ramirez, with Corey Kluber just behind them at 12th on the list. They’re losing Cody Allen, Michael Brantley, Josh Donaldson, and Andrew Miller to free agency this year, and their middle-third payroll dictates that not all those players will be returning. The club had holes in the outfield even before losing Brantley.

This puts Cleveland in the tough middle phase of a mid-market club’s playoff run, where they’re forced to maintain some quality at the major-league level even as they slowly lose the advantages created by their most valuable contracts. Luckily, they’ve continued to improve their rotation with Trevor Bauer, Shane Bieber, and Mike Clevinger all emerging and Triston McKenzie on the way. Factoring in Kluber and Carlos Carrasco makes the rotation the strength of the team, aside from the two dynamic infielders.

There is prospect capital in the lower minors, particularly the fruit from one of the better international programs in the game, but the trade value for those sorts of players will be much better in a year or two, as they establish some track record. If the Indians can remain a 90-ish-win team for 2019 without sacrificing value from future years, they are positioned for a key decision. After the 2019 season, they could to push their chips in again and extend the window for this group (followed by a full rebuild, a la the Royals right now), or do the more prudent long-term things and have a much shorter and less painful reload to reopen a new window (like the Yankees a few years ago).

5. Atlanta Braves

If I wrote this list a year ago, the Braves would be the sleeper organization sitting outside the top tier — likely outside of the top 10 — that I’d say has the potential to jump into this tier if everything comes together and ahead of schedule. That’s precisely what happened this year. At the same time, the Marlins continued to rebuild, the Mets continued to Mets, the Nationals took a step back, and the Phillies failed to leap as far ahead as their early-season results suggested they might. As a result, Atlanta emerged from the NL East as champions.

No team in this division appears poised to roll out a top-five payroll over the next few years, as industry chatter has the Nationals looking to reduce spending this winter. In lieu of a financial advantage, the Braves’ embarrassment of young MLB-ready or MLB-proven talent gives them an edge in terms of quality of players and depth. This effectively gives them something approximating a financial advantage against the division, whenever they choose to fully use it; industry chatter suggests the Braves won’t be cashing in all of their chips this offseason.

The Braves have the best farm system of the clubs in this top tier and arguably have the best controllable MLB talent, as well, with Nick Markakis and Kurt Suzuki headlining the pending free agents. The farm system has lost some depth, and international sanctions will limit the opportunity to add to it in coming years, but it will take years before that will be felt in any real way. If this group of young players develops as expected, there will be little effect at all.

I should mention, as most of you know, that I worked for the Braves recently and betting on a young core continuing at a certain trajectory can be shaky (the Mets being a recent example), but everyone with whom I spoke said the Braves clearly belong in this top tier, in part due to their core and in part to the presence of more young depth than most upstart clubs have possessed in past years.

6. Boston Red Sox

One on hand, this team has a roughly 60% chance (according to the oddsmakers) to win the World Series this year and had the best record in baseball this season (plus the marquee players to suggest it wasn’t a fluke).

On the other hand, Nathan Eovaldi, Craig Kimbrel, and Ian Kinsler are all expected to enter free agency after the World Series, while Xander Bogaerts, J.D. Martinez, and Chris Sale can walk after 2019, and Mookie Betts and Jackie Bradley Jr. after 2020. Boston has the money to probably sign sign four of these to long-term deals. Betts would seem to be the most likely to get an extension to keep him from hitting the open market.

Beyond that group, the core players are Andrew Benintendi, then some guys who are talented but somewhat unpredictable in Rafael Devers, David Price, and Eduardo Rodriguez. As for reinforcements, you’ve got the 29th-best farm system with no impact on the horizon, and some issues that sound familiar to Tigers fans after Dave Dombrowski left for Boston.

The payroll is here to keep at least half of the core, but I would imagine the Yankees will become the favorites in that race to avoid the elimination Wild Card game once a few pieces leave Boston. That is why I said earlier that, over the balance of this five-year window, starting next season, it’s close to a 50/50 proposition which of Boston and New York will avoid that Wild Card game and have the much easier road to a title. Anything can happen, but a core built around Andujar, Sanchez, Chad Green, Aaron JudgeLuis Severino, Giancarlo Stanton, and Gleyber Torres is a better bet for this kind of exercise, with all of those tied up for at least four of the five years we’re considering and all but Stanton at well-below-market rates.

7. Chicago Cubs

The Cubs looked to be on the verge of becoming a dynasty, but things have gone a bit sideways in the last year or so. It’s unclear what Addison Russell’s future is with the club (which is the least important part of his situation); Kris Bryant, Ian Happ and Jose Quintana had down years; basically the entire pitching staff was worse in 2018 than expected, Willson Contreras has some questions about his defense that would greatly impact his long-term value; there are questions about Joe Maddon’s future with the club; and Jason Heyward is making $106 million over the next five seasons.

Now, some good things have happened, like the emergence of Javier Baez and bounce-back years from Kyle Schwarber and Ben Zobrist. There’s still a lot of veteran talent and a big payroll to support such a club. That said, there’s less talent here than on the Red Sox — who I showed above need to be thinking about who to lock up and when — and this situation has some similarities with the Giants, who have been slapping a new coat of paint on the same aging core a little too long and it’s caught up with them.

The Cubs farm system is better than the Red Sox’, but there isn’t a impact type guy here who will prop things up. It’s more depth types and lower-minors types who need to prove themselves. Like the Red Sox, there’s plenty of talent and payroll here to supplement a playoff club and extend its life a bit longer, but it’s going to take more magic that it appeared was necessary a year ago.

Some argued for a couple more teams in this top tier, and a number of organizations are lingering if a few things fall their way:

  • The Angels have a high payroll ceiling and the best player in baseball, along with Shohei Ohtani at the minimum salary and an improving farm system. They also have a tough division, Albert Pujols’ contract, and an uneven recent track record.
  • The Phillies have a high payroll ceiling and you could argue they’re just a year or two behind the Braves in the same process. That said, they’ve indicated they won’t spend wildly this offseason, and all but two players in the whole organization are reportedly available in the right deal, so most would like to have a little more certainty about the specific direction.
  • The Brewers were one game from the World Series, have a nice core, and possess arguably the most well-regarded front office in baseball. That said, it’s hard to crack this top group as a perennial contender at this kind of payroll disadvantage and without a top-tier farm system.
  • The same goes to the Rays and A’s, who often carry the two lowest payrolls in the game but who both assembled playoff-caliber clubs this year. The Rays also have a clear top-five farm system. The margin for error here is so small, I can’t imagine either organization being in the top tier of this sort of ranking, even if they are able to pull of consecutive playoff appearances. The exception would be multiple pre-arb perennial All-Stars popping up at once; Matt Chapman qualifies as such and Wander Franco is on the road to becoming one, so it’s not impossible.
  • A number of others could move into the top 10 with some breaks. The Nationals are at a crossroads this offseason. The Cardinals are solid each year and across departments. The Jays have a high payroll ceiling and two top-10-overall prospects. The Twins are moving in a good direction across the board. Colorado just made the playoffs. There are also a number of rebuilding/reloading teams could accelerate their plan with a breakthrough in the next year or two.

We hoped you liked reading Here’s Who Will Win the Next Five World Series by Kiley McDaniel!

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Kiley McDaniel has worked as an executive and scout, most recently for the Atlanta Braves, also for the New York Yankees, Baltimore Orioles and Pittsburgh Pirates. He's written for ESPN, Fox Sports and Baseball Prospectus. Follow him on twitter.

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Original Greaser Bob
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Original Greaser Bob

Can’t wait to read the comment section in about 24 hours.

420Smash
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420Smash

Thumbs down on John M i d d l e t o n and Matt Klentak in Philly.

Rebuilds are not automatic success stories.

numb and number
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numb and number

Lol…looks like the F E L O N Y F R A U D guy is transitioning……