In 2014, the Baltimore Orioles gave pitcher Ubaldo Jimenez a 4-year, $50 Million Dollar Contract. Jimenez had played 6 seasons with the Rockies, pitching the first no-hitter in Rockies history. After a subpar season in 2011, he was traded to the Indians. After two poor seasons when his ERA was over 5.00, he had a good season in 2013. He finished at 13-9 with an ERA of 3.30.
With that one good season in mind, the Orioles committed $50 million to a pitcher who earned about $16 million in his whole career of 9 seasons. The results were every bit as bad as you might guess; during his 4 seasons, he only won 32 games, losing 42. His ERA during that time was 5.22.
The Orioles provided a nice retirement plan for Jimenez to get a sub-par Starter for 4 seasons.