It is normal for general managers to drop the ball when it comes to investing in talent. Nobody is perfect. Two years after signing with the Chicago Cubs, Theo Epstein made a bold decision by signing right-hander Edwin Jackson to a four-year, $52 million contract.
Keep in mind, he had already gone out and acquired first baseman Anthony Rizzo from the San Diego Padres in 2012. Of course, that amounted to a trade that cemented a blueprint designed for success following his remarkable and historic tenure with the Boston Red Sox.
When the deal was finalized, Jackson was inserted into a starting rotation that included Jeff Samardzija, Travis Wood, Carlos Villaneuva and Matt Garza.