Alex Rodriguez’s second quarter-billion-dollar-plus contract in 2007 was large enough to boggle minds and reign as the industry standard for nearly a decade. But now, it’s clear the top end of baseball’s market has caught up.

Mike Trout's new record-setting deal with the Angels not only cements his status as the best player in the game today; it also significantly raises the ceiling for player contracts in North American sports. His closest competitor, Bryce Harper, held the record for less than three weeks. In fact, the three largest contracts -- and four of the top five -- were inked within the span of one month prior to the 2019 season.

With Trout now at the head of the class, here’s a rundown of the 10 largest contracts -- be it via free agency or an extension -- in baseball history:

1. Mike Trout, Angels: 10 years, $360 million (2021-30)

Originally, this was reported as a 12-year deal worth $430 million, but Trout was already under contract for 2019 and 2020 for $66.5 million in total, so it's really a 10-year extension, which is still the biggest contract the sport has ever seen. In total, he will earn $426.5 million over 12 years.

Trout's blend of youth and talent were evident as soon as he burst onto the scene full-time with Los Angeles in 2012, when he captured the American League Rookie of the Year and finished runner-up to Miguel Cabrera in the MVP vote at age 20. He’s seemingly gotten better every year since then, compiling the most WAR of any position player in history (per Baseball-Reference) through his age-26 season.

That prodigious start compelled the Angels to reward Trout with this extension, which also allowed him to eclipse Zack Greinke's record for average annual value and, notably, did not include opt-outs. Barring something extraordinary, Trout will be an Angel for the rest of his career.

2. Bryce Harper, Phillies: 13 years, $330 million (2019-31)

The question of which team Harper would eventually play for loomed over the star seemingly as soon as the Nationals selected him with the No. 1 overall Draft pick in 2010. So, it’s safe to say his free agency drew a fair amount of attention. After four full months of speculation and a rotating carousel of suitors, long-term security -- and a record haul -- ultimately won the day. Harper signed with the Phillies for a deal that included a full no-trade clause and no opt-outs, meaning the fate of he and Philadelphia’s beloved franchise are seemingly intertwined for the rest of his Major League tenure.

3. Giancarlo Stanton, Marlins: 13 years, $325 million (2015-27)

Stanton represented Miami’s first homegrown superstar since the franchise dealt away many of the pieces from its 2003 World Series championship club, and owner Jeffrey Loria attempted to keep Stanton in South Florida as long as possible with this landmark deal that blew past Rodriguez’s record for total value. It was a major commitment from Stanton’s side as well, as the Marlins had not reached the postseason since winning that title in ’03.

Stanton enjoyed some prolific seasons in Miami -- including a memorable 59-homer, NL MVP campaign in 2017 -- before the Marlins traded him to the Yankees to kickstart a rebuilding phase just weeks after he took home the MVP hardware. Stanton has an opt-out clause that he can initiate after the 2020 campaign.

4. Manny Machado, Padres: 10 years, $300 million (2019-28)

Machado and Harper’s dueling free agencies defined the 2018-19 offseason, as the two players (and their rival agents, Dan Lozano and Scott Boras) aimed for the new free-agent standard. While Harper and the Phillies tied their fortunes together, Machado’s deal with San Diego -- baseball’s first $300 million free-agent contract -- included an opt-out after Year 5. But the Padres’ bright future with the game’s top farm system in tow could ultimately build a perennial winner around their new superstar talent.

5. Alex Rodriguez, Yankees: 10 years, $275 million (2008-17)

While the Red Sox were sewing up a World Series sweep of the Rockies, their rival’s biggest star stole headlines when Boras announced that Rodriguez would be opting out of his final three years with New York. While A-Rod later expressed regret about the way the opt-out was handled, he and the Yankees were able to come up with a most amicable solution by December 2007: A new bar for MLB’s richest contract that made Rodriguez the first player to sign two separate contracts of at least $250 million. The slugger powered the Yankees to their 27th World Series championship two autumns later.

6. Nolan Arenado, Rockies: 8 years, $260 million

If the historic 2018-19 offseason had a consistent theme with its headliners, it was probably comfort. That was certainly the case with Arenado, who could have dominated the 2019-20 free-agent market but opted instead to sign an extension with his original club that (briefly) gave him the highest average annual salary for any position player in history. Colorado’s motivation was pretty simple: Arenado had averaged 40 homers and 126 RBIs over the four seasons leading up to the extension, and he was also seen by many as the sport’s best defender at third base.

7. Alex Rodriguez, Rangers: 10 years, $252 million (2001-10)

Baseball would never be the same after A-Rod signed this landmark deal at age 25. His deal with Texas more than doubled pitcher Mike Hampton’s previous-record $121 million deal with the Rockies, signed just days before Rodriguez put his pen to paper. It also doubled Kevin Garnett’s $126 million contract with the NBA’s Timberwolves in 1997 for the largest contract in North American sports.

A-Rod spent only three seasons of this deal in Arlington, of course, before the Rangers dealt him to the Yankees. But it’s easy to argue he lived up to the deal: From 2001 until Rodriguez signed his second record deal mentioned above, he averaged 47 homers, 130 RBIs and 8.1 bWAR per season and captured three AL MVP awards with Texas and New York.

8. Miguel Cabrera, Tigers: 8 years, $248 million (2016-23)

Cabrera’s first six seasons in the Motor City included three batting titles, one home run title, the 2012 AL Triple Crown and back-to-back league MVPs in ’12 and ’13. So, the Tigers saw they all they needed to see by March 2014 to give Miggy a record extension for the time, adding an eight additional years to the final two years of Cabrera’s existing deal to pay him $292 million over the next 10 seasons.

"If you're ever going to take a chance, and to get a deal done you have to take that chance, I would take the chance on him," said Tigers president and general manager Dave Dombrowski. Cabrera pocketed three more top-10 MVP finishes and another batting title in 2015 before injuries began taking their toll in '17.

9 (tie). Robinson Canó, Mariners: 10 years, $240 million (2014-23)

Cano had ascended from Derek Jeters’ precocious double-play partner to one of baseball’s very best hitters by the time he signed his landmark deal with Seattle, racking up five All-Star selections and AL Silver Slugger Awards during his time with the Yankees. Now a Met, Cano remains on a Hall of Fame-level track, though his 2018 suspension for violating MLB’s performance-enhancing drug policy could complicate his candidacy.

9 (tie). Albert Pujols, Angels: 10 years, $240 million (2012-21)

Pujols had so engrained himself in Cardinals’ lore that it was downright shocking when he inked his mega-deal with the Angels in December 2011. The three-time NL MVP and two-time World Series champ netted himself an unusual amount for a player entering his age-32 season, but the Halos saw an opportunity to sign a franchise-altering talent who would tick off many incredible achievements in Orange County.

Though injuries held Pujols from duplicating his St. Louis success with Los Angeles, he has indeed written several of his milestones with the Halos. Pujols hit his 600th home run and knocked his 3,000th hit in Angels red, and will likely drive in the 2,000th run of his career in 2019.