The saga of Bryce Harper and Manny Machado’s search for a new home has finally come to an end which means it’s time to start obsessing over the next big free agent contracts.

While we’ll certainly miss the Bryce-Manny Tracker, the wave of superstars following them to pick out their own Brinks truck will provide just as much excitement in their hunt for a new contract.

Among the top five free agents who should cash in are three MVPs, three World Series champions and arguably the greatest player in baseball in generations.





BOSTON, MA - JUNE 26: Mike Trout #27 of the Los Angeles Angels walks toward the on-deck circle before a game against the Boston Red Sox at Fenway Park on June 26, 2018 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images) More





1) Mike Trout, OF

Free Agent: 2021

If you thought the courtship of Bryce and Manny was a circus, just wait until Trout hits the open market in 2021— assuming the Angels don’t lock him up before then. Trout will be coming off his 10th MLB season and just a few months removed from his 28th birthday. Could he become the first North American pro athlete to sign a $400 million deal? Possibly, but a lot needs to go right before then. The current collective bargaining agreement between the MLB and MLBPA expires in 2021 and both sides have already begun digging in for what’s expected to be intense negotiations.

Assuming baseball doesn’t suffer a catastrophic failure and wind up with a strike or lockout, Trout could enter the 2021 season not only as the best player in baseball but the highest-paid one, too.

You’d have a tough time finding anyone who doesn’t think Trout is the most gifted two-way star in the game. Finding out how much teams are willing to pay for that kind of talent will be one of the more fascinating storylines of the next few seasons, especially if he keeps up his average of 9.11 Wins Above Replacement per year since 2012.





2) Mookie Betts, OF

Free Agent: 2021

It was hardly a year ago when comparisons between Betts and Trout seemed farfetched at best. Oh, how quickly the things change. The fully formed version of Mookie Betts dominated the American League in 2018 en route to a World Series title and MVP award. For his contributions in Boston last year, Betts won a 2019 salary of $20 million in arbitration. He has one more year left of arbitration eligibility in 2020 before hitting free agency.

Betts will be just 27 years old then with at least three All-Star appearances, three gold gloves and two silver sluggers. It’s hard to imagine he won’t add to his trophy case between now and then.

He likely won’t get the money Trout is after, but second place in that contest will hardly be viewed as a consolation prize.

Whether or not the Red Sox will fork over that kind of cash is another issue altogether. Despite having MLB’s highest payroll over the last two years, the club has been reluctant to empty out its bank account on big-name free agents in the past few years. That was certainly the case when the Red Sox low-balled Jon Lester in 2015 before losing him to the Cubs for $155 million. Last season, when 29-year-old J.D. Martinez went searching for a top-tier contract, it was Boston that got him at a relative discount of $110 million over five years. That’s to say nothing of the Red Sox walking away from closer Craig Kimbrel this offseason despite a need for a premier closer in their bullpen. It’s also doesn’t take into account the expiring contract of the next person on this list.





3) Chris Sale, SP

Free Agent: 2020

The biggest threat to Betts’ ability to remain in Boston without sacrificing potential earnings is sitting just across the clubhouse from him. Chris Sale’s impending free agency after the 2019 season has been a long time coming. Sale is on a notoriously club-friendly deal — $32.5 million/five years —and while he’s already indicated he’d sign an extension before hitting the open market, the 30-year-old could ask for an extra zero on his check for each batter he strikes out and still be considered undervalued.