7 Pitchers Who Will Win A World Series Before They Retire, 7 Who Have A Chance, And 7 Who Won’t

Chicks dig the long ball, the famous baseball joke tells us, but home run hitters can only do so much to help a team win a World Series. After all, even the best slugger struggles to average one round-tripper per postseason game, and he is lucky if he reaches the plate a total of five times in any given day. A top-tier pitcher, meanwhile, can be on the bump for nine total innings, if he’s dominating, of a World Series game. As defense wins championships in the National Football League, World Series titles are often won and lost because of starting and relief pitching.

A handful of pitchers who have not yet been to the figurative mountaintop will eventually receive opportunities to win at least one World Series ring. Some will be part of a banner-raising ceremony, while others will fall short, maybe due to zero faults of their own. Remember that no one person will win or lose a World Series. As we saw with the 2018 New York Mets, even the best pitcher in Major League Baseball can only do so much if his lineup does not offer him any run support when he is on the hill. That poor guy should get another shot to win a World Series before he retires.

21 Will Win: Blake Snell

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Tampa Bay Rays starter Blake Snell was a revelation for his club during the 2018 campaign. The 25-year-old ended the season with a league-leading 21 wins, and his 1.89 ERA was downright jaw-dropping. As long as he remains healthy, Snell has probably not yet hit his prime and his best days as a starter. The future is very bright for the young man even if Tampa Bay is not known as an organization capable of competing with the likes of the New York Yankees and Boston Red Sox. His time to pitch in a World Series will come even if he has to make a move from the Rays.

20 Has A Chance: Trevor Bauer

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All things considered, Trevor Bauer may have become the real ace of the Cleveland Indians during the 2018 campaign. When he is at his best and not playing with devices that are capable of slicing his hand open during an October postseason run, Bauer has the kind of stuff that makes for nightmares for opposing hitters. Some may not realize that Bauer is only 27-years-old, meaning his future remains bright even if it is in question. He should have a chance to win a World Series with the Tribe as long as the Indians remain the class of the division, which seems likely up through the end of the decade.

19 Won't Win: Bartolo Colon

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There are two types of baseball fans: Those who love Bartolo Colon, and those who have wrong opinions and incorrect feelings. “Big Sexy,” as he has become affectionately known among fans over the years, apparently wants to continue pitching through 2019 even though he will be 46-years-old before the summer months. The hope is that some team, either one that needs a veteran to eat innings up or a losing club that is desperate for a pitcher, will give Colon an invite for spring training sessions. The baseball world will be worse off when Colon is no longer in the league. May he pitch forevermore.

18 Will Win: Luis Severino

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One would not have to look all that far to find hot takes that New York Yankees starter Luis Severino cannot handle the pressure of pitching in playoff games and blah blah blah. He’s 24-years-old, and he just had the best season of his young career. Maybe, just maybe, let’s let Severino approach flirting with turning 30-years-old and have a few more postseason games under his belt before we start throwing around opinions about what he can or can’t do as it pertains to a potential World Series appearance. The Yankees are going to be excellent in the 2020s, and Severino should be part of that equation.

17 Has A Chance: Miles Mikolas

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Who among you even noticed in December that the St. Louis Cardinals signed a pitcher named Miles Mikolas? Largely out of nowhere, Mikolas went from performing overseas to winning 18 games for what is largely respected as one of the top organizations in all of professional baseball. We don’t yet know what is in the future of the 30-year-old other than the fact that he is currently set to be part of the Cardinals for one more season. Will the Cardinals compete with him on the roster? Will he join a different contender before the end of the current decade? These unknowns are why he is among pitchers who have a chance to win a World Series.

16 Won't Win: David Price

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Let’s all agree to be honest and admit that none of us have any faith that David Price will be on the hill for a World Series-winning drive for the Boston Red Sox or any other team in the league. Heck, even the Red Sox apparently have serious doubts about putting Price on the hill for the start of a postseason day these days. Maybe, just maybe, the Red Sox will be able to get past one poor starter and get to the championship in October 2018, meaning this prediction will look rather silly. If that doesn’t happen, though, one has to wonder how many additional opportunities he will receive in the future.

15 Will Win: Aaron Nola

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Some out there, most of whom are fans of the Philadelphia Phillies, would say that Aaron Nola was the best pitcher in the National League this season. Nola finished his age-25 season with a career-high 17 wins, and his 2.37 ERA and 0.97 WHIP would be even more impressive if not for the numbers posted by a certain division rival who has already pitched in a World Series. Nola should have plenty of opportunities to perform in an October Classic, either with his current club or with a different team if/when he moves on from the Phillies. We have no reason to believe we have yet seen the best from Nola.

14 Has A Chance: Carlos Carrasco

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Much of what was written about Trevor Bauer is also accurate regarding Carlos Carrasco, Bauer’s teammate with the Cleveland Indians. Carrasco left no doubt in 2018 that he has the goods to compete for a Cy Young in the future as long as he is able to remain healthy for at least a few more seasons. The 31-year-old should see a couple of more chances to pitch in and win meaningful October games with the Tribe. Any team that wins its division and makes it to the postseason could win the World Series, which is why Carrasco should have a chance to earn a ring during his career.

13 Won't Win: Rich Hill

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Here’s another person who could prove this prediction wrong if his club goes on to win the World Series in October 2018. If the Los Angeles Dodgers are not the last team standing at the end of the season, though, then Rich Hill is running out of chances to get his ring. Hill will be 39-years-old by the start of the 2019 season. While he is no longer an MLB castoff, Father Time and age are going to catch up with him sooner rather than later. Hill could be part of another playoff team a year from now since the Dodgers should be able to spend and compete again. 2019 could be it for him, though.

12 Will Win: Masahiro Tanaka

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The New York Yankees were not supposed to get to the point of competing for a World Series berth so soon, but their young talent is already championship-ready even if the Yanks are not quite where the Houston Astros and Boston Red Sox are today. Assuming that we are on the cusp of witnessing the next Yankees dynasty, Masahiro Tanaka should be part of that process. Tanaka turns 30 years old in November, and there is no indication that the Yankees will look to move on from him even if the team adds an ace via free agency or a trade before the start of the 2019 season.

11 Has A Chance: Max Scherzer

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We’re not quite sure what to think about what is going on with the Washington Nationals as of the fall of October 2018. For starters, it appears as if the club is about to lose its biggest star. Max Scherzer, on the other hand, probably isn’t going anywhere for the foreseeable future because of the contract that ties him to the club up through the 2021 season. While Scherzer may not retire as a member of the Nationals — a lot can and will happen over the next three years — Washington could struggle to return to the postseason in 2019, especially if the New York Mets are able to stop embarrassing themselves for longer than a month or two.

10 Won't Win: Wade LeBlanc

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Southpaw Wade LeBlanc is not your ordinary journeyman. While some merely travel to and from clubs located in North America, Wade LeBlanc has pitched both in MLB and in Japan. Most recently, the 34-year-old southpaw enjoyed a second stint with the Seattle Mariners, one that could continue up through 2022 depending on how well or how poorly he performs in the team’s colors. The veteran is probably not the first or last name that comes to mind for such a piece, but his 2018 season could be considered a “breakout year.” Maybe a contender would take a flier on grabbing him in 2019. Still, we’re predicting LeBlanc won’t win a World Series.

9 Will Win: Chris Sale

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Fans of the New York Yankees had to feel absolutely helpless watching Chris Sale pitch a scoreless inning out of the bullpen for the Boston Red Sox during the final game of the ALDS. The 29-year-old lefty can be the best in the business when he is on his game, and it’s possible he could win the World Series as soon as the month that this piece is published. The Red Sox should be back in contention a year from now regardless of what happens in the 2018 ALCS/World Series, and Sale should be part of that process for another campaign. Boston may be the team to pay him, and in a big way, come 2020.

8 Has A Chance: Mike Clevinger

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Two things one should realize about Cleveland Indians pitcher Mike Clevinger: He is still only 27-years-old, and he should probably think twice about entering into Twitter feuds with MLB Network personalities. Like the two previously mentioned Cleveland pitchers and the man mentioned later in this piece, Clevinger should have more chances to pitch in October as long as the team remains the best in the AL Central. From there, it’s anybody’s guess what the Indians will or won’t be able to do against the best teams in the AL. For the now, Clevinger remains a young gun who has a chance to win a World Series.

7 Won't Win: Stephen Strasburg

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There is still so much time left in the career of Stephen Strasburg that it admittedly seems a little silly to begin predicting that he will never win a World Series. Even if the Washington Nationals fall off a cliff and dip down the division standings, Strasburg, who turns 31-years-old next summer, probably wouldn’t have to search far to find a contender that would want to utilize him for a postseason run. Even still, there is the perception that he might be a little snakebitten as it pertains to his overall legacy and his future. Maybe some guys just are destined to never win a World Series.

6 Will Win: Noah Syndergaard

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At just 26-years-old, Noah Syndergaard is too good to not win a World Series before he retires, right? One would think, even if the New York Mets are never able to make the most out of having Thor, among others, in the rotation. There will come a day when Syndergaard is one of the hottest commodities on the market. Perhaps he will remain with a Mets team that stops being allergic to spending big money on the top players available, or maybe he will journey to a different contender that makes him a very rich man. Either way, Syndergaard is going to have more than one chance to win a World Series.

5 Has A Chance: Zack Wheeler

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The New York Mets shutting Zack Wheeler down early was the right business decision for player and club alike. Those who watched Wheeler during the second half of the 2018 season had to like what they witnessed, so much so that he has to be viewed as a contender to potentially win a World Series over the next decade. There are still plenty of questions to be asked regarding what Wheeler will be following the best season of his career. How much better will he get? What is his ceiling? Is he part of the long-term solution for the Mets, or will he be a piece of a future trade that brings an All-Star to the Amazins?

4 Won't Win: Zack Greinke

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Money isn’t everything, or so the saying goes, but odds are Zack Greinke wouldn’t know anything about that. According to Spotrac, Greinke could make over $300 million off of MLB contracts alone before the 2026 regular season comes to an end. At 34 years old, Greinke’s window to win a championship isn’t shut, but the Arizona Diamondbacks are not just a piece or two away from becoming the best team in the NL, let alone the top side in MLB. Greinke could afford to buy his own ring in the future if such things matter to him, but it is not a stretch to suggest he won’t win a World Series.

3 Will Win: Jacob deGrom

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It will be downright criminal if Jacob deGrom does not win a World Series before he retires. The best pitcher in all of MLB for 2018 was repeatedly hung out to dry by New York lineups who couldn’t score runs when he was on the bump, otherwise, he would have easily notched 25 victories on the season. Optimistic fans may honestly believe that the Mets are not as far off as others imagine heading into the offseason, and it’s possible deGrom could still be the ace for the club when it returns to the playoffs. Some other World Series contender could offer a boatload of assets to the Mets to grab him as soon as 2019.

2 Has A Chance: Corey Kluber

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Only a couple of years ago, Cleveland Indians ace Corey Kluber would have been a favorite to make the list as a pitcher who will definitely win a World Series. Kluber’s struggles during October games coupled with some real health concerns have dropped him into the “have a chance” portion of the list. The 32-year-old can still be the best pitcher in baseball, but Cleveland’s window to win a World Series isn’t as open as it was in October 2016. There are even some within the Cleveland fan base who believe that now is the time to sell Kluber to the highest bidder while he’d still be worth something in a trade.

1 Won’t Win: Matt Harvey

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One could feel a little sorry for Matt Harvey, a pitcher once capable of winning a Cy Young and earning a $300 million payday but now one who may have to settle for a contract from whatever team will tolerate him in 2019. Harvey was unable to close the Kansas City Royals out in his last World Series appearance, and nobody has a reason to believe that he will get back to the October Classic with any club. At just 29-years-old, Harvey’s prime and his best days are but a memory, as injury woes stripped what should have been a stellar career from him.

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