David Price, 2015
Here is the first line from Bob Nightengale's story in December 2015.
"David Price teed off Tuesday morning at a charity golf tournament in Las Vegas believing he would be spending the next seven years pitching for the St. Louis Cardinals. By the time he left the event hosted by former major leaguer Wally Joyner, Price had agreed to become a member of the Boston Red Sox with a deal that will make him the richest pitcher in history."
Price was signed to a seven-year, $217 million contract by the Red Sox, which was reportedly at least $30 million more than what the Cardinals had offered him.
At the moment, the deal made a ton of sense for Price. He was coming off his age 29 season where he went 18-5 with a 2.45 ERA for the Detroit Tigers and the Toronto Blue Jays and was second in Cy Young voting that year. But most people would agree that the deal went poorly though.
Although he helped the Red Sox win a World Series, he went 53-26 with a 3.78 ERA in 700 innings of work. He wasn't a bad pitcher the first three years of the deal, but overall, he wasn't the kind of pitcher you give a record deal to.
That kind of contract is an issue on your books, even for a team like the Red Sox or Dodgers, but imagine if the Cardinals had that deal, even at $30 million total less than what he got in his deal. That would have hamstrung their pocketbooks for years and would have been a huge disaster.