Baseball's Five Highest Paid Players in 2019

By Jeff Weisinger

The game of baseball suffered a bit of a crisis during this year’s free agent period. To put it simply, teams weren’t willing to pay anything for players who wouldn’t completely change the course of their franchise, and when they did find one of those players, agreements wouldn’t be reached until after days and weeks of negotiation.

Some of the best players available went all the way to the draft without getting signed. Still, that doesn’t mean there wasn’t some big money thrown around at the end of the day.

Both Bryce Harper and Manny Machado stretched out their free agency until signing deals worth $300 million and more, and Mike Trout, the game’s best player, stayed patient and got his record-breaking deal north of $400 million.

Here are some of baseball’s highest-paid players in the 2019 season:

5. Albert Pujols, Los Angeles Angels – $28 million

Pujols has two years left on his 10 years, $240 million deal he signed back in 2012. The future Hall of Famer’s numbers have declined in his late 30’s, but he’s still one of the most feared hitters in the game. He’s played over 100 games and recorded double-digit home run totals in every year of his career; however, last year was the first since 2013 where he didn’t hit more than 20 homers. A lot of money for a star on his last legs.

4. Yoenis Cespedes, New York Mets – $29 million

Yoenis Cespedes might be a signing that Mets fans want to forget about already. After a stellar 2015 season where he helped guide the Mets to its first World Series appearance since 2000, he’s been injured more than he’s played. He’s only played in a combined 119 games over the last two seasons and has yet to play this year as well. However, when healthy, Cespedes is one of the better, more powerful outfielders in the game. But those moments have been few and far between.

3a. Bryce Harper, Philadelphia Phillies – 2019 Total: $30 million

Harper was the biggest catch of the winter and while the track record on players who sign long term, mega-million deals aren’t all that great, the Phillies decided to do it anyway and signed Harper to a 13-year, $330 million deal. At just 26, the deal seems appropriate since the Phillies would like to keep him for the rest of his career. His front-loaded contract gives more of his money up front, as he’s expected to get $26 million from the Phillies from 2020-28, then $22 million per year for the final three years of his deal.

Plus, when you toss in his $20 million signing bonus his endorsements from partners like Under Armour, Rawlings, Sony, and Gatorade, he’s bringing home a total of $39 million this year. All in all, Harper got what he was looking for in free agency.

3b. Manny Machado 3B, San Diego Padres – 2019 Total: $30 million

Like Harper, Machado also got a $20 million signing bonus when he signed a 10-year, $300 million with the Padres over the winter. He’ll make nearly as much this year alone as he did in his first seven years in the league ($34 million).

A four-time All-Star and a two-time Gold Glover, Machado is proving his worth to San Diego this season, hitting .278 with 16 home runs and 47 RBI. It’s a hefty premium to pay for any player, but San Diego needed a superstar to complement the prospects they have coming up the pipeline. Machado provides that, and brings baseball excitement to San Diego for the first time in a long time.

3c. Miguel Cabrera, 1B, Detroit Tigers – 2019 Total: $30 million

Although the now 36-year-old Cabrera was sidelined with injuries for a majority of last season, he’s still one of the best active home run hitters in the game, second behind Albert Pujols in career home runs and runners batted in. He’s still on the books with the Tigers through 2023, with two team options for 2024 and 2025 after signing his 8-year, $248 million deal back in 2016.

Cabrera did great things for Detroit in the early years of this decade, but his injuries and the team’s rapid decline has made for a slow march to the finish. A lot of money to be paying, but the Tigers probably don’t mind paying homage to one of the best hitters in history and giving him his money.

2a. David Price, SP, Boston Red Sox – 2019 Total: $31 million

Price played a big role in guiding the Red Sox to the World Series last year, finally proving he was worth his big $216 million deal he signed back in 2016. He went 16-7 with a 3.58 ERA, but posted his best WAR total (4.4) since his 2010 season in Tampa (4.7).

His back-loaded deal has him making $31 million from the Sox this year and $32 million in his next three seasons with Boston. Price helped bring the city a World Series, but faces an important season for his legacy; if he can prove last year’s performance in big spots wasn’t a fluke, he’ll earn his money and then some.

2b. Clayton Kershaw, SP, Los Angeles Dodgers – 2019 Total: $31 million

Kershaw gambled on himself last offseason. He opted out of a player option with Los Angeles that would’ve paid him $64 million in the next two seasons, and instead signed a three-year, $93 million deal with the Dodgers. The contract also has a lot of monetary incentives built into it; Kershaw can count on $31 million annually, and an additional $1 million bonus for his 24th, 26th, 28th, and 30th starts, respectively.

Should he reach those milestones, he could earn up to $35 million from the Dodgers this year. He’s averaged about 25 starts the last three seasons and has made 30+ starts three times in his career, so it seems like he could reach at least a few of those incentives. He’ll also earn an extra $1.5 million if he wins the Cy Young and just $500,000 if he finishes either second or third in the race.

After an 18-7 season in 2017, he struggled to just nine wins last season. He’s currently 7-1 with a 2.85 ERA this year in 12 starts. Kershaw still can make a case for best pitcher in the league, but paltry playoff performances in the last two seasons have raised questions about his ability to perform under pressure.

1. Mike Trout, Los Angeles Angels – $36 million

Mike Trout didn’t just get paid with the Angels over the winter.

He got P-A-I-D.

Trout signed a 12-year, $426.5 million deal over the winter, breaking the hearts of every baseball fan who wanted him playing for their team in 2020 and breaking the record for the biggest total payout in team sports. His deal was about $4 million shy of Floyd Mayweather’s record individual total of a  $430 million payout during his 30-month deal with Showtime.

Trout will earn a total of $39 million this year with $3 million coming from endorsements. But, more importantly, Trout is worth every penny and has proven it. He’s hit over .300 in each of the past three seasons (and is hitting over .300 this year), has become a perennial All-Star and a perennial Silver Slugger outfielder, taking home the award in six of the last seven seasons.

All he really has to do now is win a World Series or two to lock himself in for a place in Cooperstown.