When Gerrit Cole inked a nine-year, $324 million deal -- the richest ever signed by a pitcher -- with the Yankees in December, it made New York home to arguably the top two pitchers in the game, as Cole joined Mets ace and reigning two-time National League Cy Young Award winner Jacob deGrom in the Big Apple.

Although they’ll be pitching for crosstown rivals, the two aces will take aim at history together in 2020.

Two players have won an MVP Award in the same season while representing the same city on a handful of occasions, including 2019 with Mike Trout and Cody Bellinger, but it’s never happened with the Cy Young Award.

Cole and deGrom will try to become the first duo to accomplish the feat in 2020, a year after deGrom won his second straight NL Cy Young and Cole finished second to former Astros teammate Justin Verlander in the American League race.

It was a narrow loss for Cole, who received 13 first-place votes and garnered 159 vote points to Verlander’s 171. Cole had a strong case, as he topped Verlander in two of the three pitching Triple Crown categories (ERA, strikeouts) and posted a FIP that was 0.63 runs lower than Verlander's while throwing only 10 2/3 fewer innings.

Of course, Cole and deGrom aren’t the first pair of elite arms to pitch in the same city concurrently. In fact, we’ve come close to having two Cy Young Award winners from the same city on multiple occasions.

Here are the six times in which a pitcher won his league’s Cy Young Award the same year a hurler from the same city finished among the top three in the other league.

2011: Los Angeles
After breaking out in 2010, Dodgers ace Clayton Kershaw took his game to an even higher level the following season, earning his first career Cy Young Award. While Phillies teammates Roy Halladay and Cliff Lee both finished with more Wins Above Replacement, per Baseball-Reference, Kershaw was an easy choice for the voters, as he won his first and only pitching Triple Crown with an MLB-best 2.28 ERA and an NL-leading 21 wins and 248 strikeouts.

In the AL, Angels right-hander Jered Weaver enjoyed what would prove to be the best season of his career, setting personal bests in ERA (2.41), WHIP (1.01), innings (235 2/3) and WAR (6.9) while recording the second-highest strikeout total (198) of his big league tenure.

However, he came up short in the Cy Young race, as Verlander pulled off the MVP-Cy Young double dip with a 24-5 record, 2.40 ERA, 0.92 WHIP and 250 strikeouts over 251 innings for the Tigers. Weaver placed second, preventing the city of Los Angeles from taking the Cy Young hardware in both leagues.

1992: Chicago
While Greg Maddux showed flashes of greatness over his first six seasons, 1992 was the year he officially arrived as a top-tier ace. In his final season with the Cubs, the right-hander went 20-11 with a 2.18 ERA and 199 strikeouts in 268 innings. His overall WAR total of 9.4 led the Majors.

Maddux edged out the Braves’ Tom Glavine for his first Cy Young Award, then joined Glavine in Atlanta as a free agent and won three more Cy Youngs from 1993-95.

The White Sox, meanwhile, had a Cy Young candidate of their own in Jack McDowell, who went 20-10 with a big league-leading 13 complete games and a 3.18 ERA over 260 2/3 innings. McDowell finished second behind A’s closer Dennis Eckersley, who also won the AL MVP Award. Maddux and McDowell were the two Cy Young Award winners the next season, but Maddux was no longer in Chicago.

1985: New York
New York City made a strong bid for dual Cy Young Awards in 1985, with Mets right-hander Dwight Gooden following up a remarkable rookie season at age 19 by turning in one of the greatest pitching campaigns in baseball history. Gooden led MLB in wins (24), ERA (1.53), strikeouts (268) and WAR (13.3), and the NL in innings (276 2/3) and complete games (16), earning unanimous Cy Young honors.

Yankees left-hander Ron Guidry, who won the AL Cy Young Award in 1978, wasn’t nearly as dominant as Gooden in ’85, but voters were dazzled by his glitzy 22-6 record. Guidry also had a 3.27 ERA over 259 innings and placed second in the Cy Young race behind the Royals’ Bret Saberhagen.

1975: New York
A decade before Gooden burst onto the scene in New York, Mets right-hander Tom Seaver won the last of his three Cy Young Awards, earning 98 vote points to 80 for the Padres’ Randy Jones after leading the NL in wins (22) and strikeouts (243) and finishing third in ERA (2.38). Seaver also had the second-most WAR (8.2) in the Majors behind Reds second baseman Joe Morgan.

The AL race was close, too, as the Orioles’ Jim Palmer edged out the Yankees’ Catfish Hunter, 98 points to 74. Hunter, who won the Cy Young with the A’s the previous season, became a free agent after arbitrator Peter Seitz ruled in his favor in a contract dispute against Oakland.

Hunter subsequently signed with the Yankees for $3.35 million, becoming baseball’s highest-paid player at the time. He went 23-14 with a 2.58 ERA over 328 innings in his first year with New York, but Palmer was 23-11 with a 2.09 ERA over 323 frames for Baltimore.

1974: Los Angeles
Dodgers reliever Mike Marshall earned the 1974 NL Cy Young Award after recording a 2.42 ERA with 21 saves over 208 1/3 innings spanning 106 games. Marshall is the only pitcher in big league history to reach the 200-inning mark in a season without making a single start.

While Marshall took home NL honors, Angels fireballer Nolan Ryan placed third in the AL race behind Hunter and the Rangers’ Fergie Jenkins. Ryan, a 324-game winner and MLB’s all-time leader in strikeouts with 5,714, famously never won a Cy Young Award, coming as close as second in 1973.

1971: Chicago
After finishing second in 1967 and third in ’70, Jenkins finally broke through in ’71, topping Seaver in the NL vote after going 24-13 with a 2.77 ERA for the Cubs. Jenkins also led the Majors in both complete games (30) and K/BB ratio (7.1).

Meanwhile, White Sox righty Wilbur Wood led all MLB players in WAR (11.0), but nobody knew it at the time because the stat hadn’t been invented yet. Wood also had an impressive season by traditional metrics, winning 22 games and recording a 1.91 ERA over 334 innings, but he came in third in the AL race behind the A’s Vida Blue (also the AL MVP) and the Tigers’ Mickey Lolich.