Evan Longoria of the Tampa Bay Rays is in what would have been his final season before free agency and headed to possibly the largest contract in baseball history.
However, Longoria signed an unprecedented 9-year contract just six days after making his Major League debut and then followed that up with another 7-year extension1 that will keep him with the Rays for at least 16 seasons through 2023.
By the time the deal is over, Longoria will be 38 and will have made a nice sum of $151.5 million in his career.
That's not bad. But it could have been a lot better.
By signing two contracts well in advance of hitting free agency, Longoria received financial security. But that safety blanket also cost him more than $100 million.
Longoria stands above his peers
In his first six seasons in the big leagues, Longoria has been worth 36.5 Wins Above Replacement for the Rays. That compares quite well to other position players who have signed long-term contracts in recent years, either as free agents or as they were nearing free agency2.
The high cost of security
Despite being one of the top players in an era when 21 players will make at least $20 million this season, Longoria will not make $20 million in any of his first 16 seasons in the big leagues, topping out at $19.5 million in 2022, his 15th season.
As a result, despite having competitive salaries early in his career, the other four players will zoom past Longoria in career earnings as they advance in age.
Those four players will have earned an average of $202.2 million through their age-37 season, $50.7 million more than Longoria will have made by the same point in his career.
Longoria may have missed out on the biggest contract in baseball history
Tim Dierkes of MLBTradeRumors.com believes that if Longoria were a free agent after this season, he would probably seek a 10-year contract larger than Alex Rodriguez's record $275 million deal. Dierkes points out that Cano was two years older than Longoria, who at age 29 would be a relatively young free agent, and if his 2014 season looks like 2011 and 2013 he will have six "elite" seasons on his resume.
"I think the Cano and [Albert] Pujols deals set a precedent for 10 years, which is easier to stomach with Longoria than it was with them3," Dierkes told Business Insider. "If I'm Longoria's agent, I'm seeking $300 million ... I think the Cano deal (10-years, $240 million) is probably the floor. I don't see a good reason why Longoria would accept less."
Longoria's career earnings start to look a lot different if he were heading toward a $240 million contract this winter.
In other words, even if we assume Longoria signs at the lower end of the projections by Dierkes, he still lost out on more than $100 million in career earnings by not becoming a free agent.
This is not to say Longoria necessarily made a mistake or that anybody should feel sorry for him. Longoria did attain some security early in his career.
But that security came with a hefty price tag.
1 This assumes that all team options are exercised.
2 Like Longoria, Robinson Cano and David Wright had their first full season at age 22 while Joey Votto and Jacoby Ellsbury did not have a full season in the big leagues until age 24.
3 Cano was 31 when he signed his deal and Pujols was 32.
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