As the sun sets on the 2019 Winter Meetings, MLB executives will head home having seen two pitchers sign record contracts in the span of 30 hours or so. The Nationals gave Stephen Strasburg a seven-year deal worth $245 million on Monday. At the time, it was the richest pitching contract in history in terms of total dollars and average annual value ($35 million).

Strasburg's records lasted one day (and a few hours). On Tuesday, the Yankees signed Gerrit Cole to a monster nine-year contract worth $324 million. That shattered Strasburg's total guarantee record, and, at $36 million, it is a new average annual record for any player, pitcher or position player. Here are the richest pitching contracts in baseball history:

  1. Gerrit Cole, Yankees: 9 years and $324 million
  2. Stephen Strasburg, Nationals: 7 years and $245 million
  3. David Price, Red Sox: 7 years and $217 million
  4. Clayton Kershaw, Dodgers: 7 years and $215 million
  5. Max Scherzer, Nationals: 7 years and $210 million

The Dodgers made Kershaw baseball's first $200 million pitcher in January 2014. Almost one year to the day later, Scherzer became the second $200 million pitcher. Chances are Cole's reign as baseball's only $300 million pitcher will last longer than Kershaw's reign as the only $200 million pitcher.

Because pitchers like Cole are few and far between, and because so many players have signed long-term extensions in recent years, there are no obvious candidates to sign a $300 million pitching contract in the near future. Jacob deGrom, the reigning two-time NL Cy Young winner, would've been a great candidate next offseason had he not signed his $137.5 million deal in March.

Cole is poised to be baseball's only $300 million pitcher for the foreseeable future, which I'm sure agent Scott Boras loves. At some point another pitcher will sign a $300 million contract though. It is inevitable. Here are eight candidates to be the second $300 million pitcher in baseball history (listed alphabetically).

Shane Bieber
CLE • SP • #57
Free agent year2024-25 offseason
Age at free agency29
2019 WAR5.0
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Thanks to the brilliant pitcher development minds in the Indians organization, Shane Bieber has made a rapid ascent from 2016 fourth-round pick to MLB ace. He threw 214 1/3 innings with a 3.28 ERA and 259 strikeouts this past season, which earned him a fourth-place finish in the AL Cy Young voting. Bieber has the tools and smarts to continue pitching at this level too. Cleveland tends to be very aggressive locking up young players, and if the team gets Bieber to take a deal soon, it would presumably delay his free agency and end his chances at a $300 million contract.

Walker Buehler
LAD • SP • #21
Free agent year2024-25 offseason
Age at free agency30
2019 WAR2.2
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Dodgers righty Walker Buehler might be the closest thing to Cole right now. He brings huge (and effortless) velocity to the table, as well as three swing-and-miss secondary pitches and very good control. He also pitches with the same confidence that borders on arrogance. He's very good and he knows it. Buehler has a 2.98 ERA with 366 strikeouts in 319 2/3 innings in two years as a full-time starter, so he's on a $300 million track. There are two things working against him though. One, he won't hit free agency until he's 30 (Cole just turned 29), and two, he's had Tommy John surgery. An age that starts with a 3 and an elbow that's already blown out once could lead to Strasburg money rather than Cole money.

Jack Flaherty
STL • SP • #22
Free agent year2023-24 offseason
Age at free agency28
2019 WAR5.9
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Everything came together for Cardinals right-hander Jack Flaherty this past season. He allowed 10 earned runs in 15 starts after the All-Star break and established himself among the game's greats. As far as a potential $300 million contract, Flaherty has everything going for him right now. He's an elite performer, he has a squeaky clean medical history, and he will become a free agent about two weeks after his 28th birthday. Flaherty is four years away from free agency and four years is an eternity in baseball. Right now though, he stands out as prime candidate to get a $300 million contract down the line.

Lucas Giolito
CHW • SP • #27
Free agent year2023-24 offseason
Age at free agency29
2019 WAR5.6
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It only feels like Lucas Giolito has been around forever. The White Sox right-hander just completed his second full MLB season, during which he broke out as a star. He posted a 3.41 ERA with 228 strikeouts in 176 2/3 innings. That earned him a sixth-place finish in the AL Cy Young voting. Giolito had Tommy John surgery almost immediately after being drafted in 2012, so, if he stays healthy between now and free agency, it will have been 11 years since the injury. That's long enough to prove your durability to teams, right? I still think it might cause him to fall short of $300 million when the time comes.

Since we have to forecast well into the future, we have to include Padres lefty MacKenzie Gore, the best pitching prospect in baseball, on our list. He had a 1.69 ERA with 135 strikeouts in 101 minor-league innings and reached Double-A this past season, so Gore could make his MLB debut late next year. Four above-average pitches with command and aptitude equals ace upside. If we assume 2021 will be Gore's first full MLB season, he won't become a free agent until the 2026-27 offseason, when he will still be only 27. A lot can go wrong between now and then, but Gore is a special prospect, and I think he should be on the $300 million contract radar.

Luis Severino
NYY • SP • #40
Free agent year2023-24 offseason
Age at free agency29
2019 WAR.9
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The Yankees just gave out the first $300 million pitching contract. Could they give out the second too? Luis Severino battled through shoulder and lat injuries this past season, but he threw well in the postseason, and he pitched like an ace in 2017 and 2018 (3.18 ERA and 450 strikeouts in 384 2/3 innings). Even if the fifth year club option in the four-year, $40 million extension he signed earlier this year is exercised -- if he's a $300 million caliber guy, of course the option gets picked up -- Severino will still be only 29 when he becomes a free agent. Staying healthy between now and free agency will be paramount after this season.

Mike Soroka
ATL • SP • #40
Free agent year2024-25 offseason
Age at free agency27
2019 WAR5.7
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I feel like Braves righty Mike Soroka did not get enough attention for a marvelous rookie season. He threw 174 2/3 innings with a 2.68 ERA and, in the year of the juiced ball, Soroka allowed only 14 home runs. His 0.72 HR/9 led the National League. A bowling ball sinker will do that. Soroka has had some arm issues throughout his career, so he's going to have to stay healthy the next few years to have a shot at $300 million, and he'll also need help from his infield defense to keep runs off the board given his middling strikeout rate (7.3 K/9). Maybe not prototypical $300 million candidate, but a candidate nonetheless, especially because he's due to hit free agency at such a young age. The Braves have signed several core young players to long-term contracts in recent years (Ozzie Albies, Ronald Acuna, etc.) and my guess is they lock up Soroka before he has a chance at $300 million.

Noah Syndergaard
LAD • SP • #43
Free agent year2021-22 offseason
Age at free agency29
2019 WAR2.3
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Easily the best $300 million candidate scheduled to hit free agency in the next two offseasons. Mets righty Noah Syndergaard is a lot like Cole when he was two years away from free agency. Cole had undeniably great stuff but hadn't yet put it together, then the Astros helped him reach his potential after coming over from the Pirates. If things click for Syndergaard in 2020 the same way they clicked for Cole in 2018, we might be talking about him potentially breaking Cole's contract record in two years. The raw stuff is overwhelming and the upside is enormous.