At the time, his big league resume consisted of 49 games over which he hit .141 with a .523 OPS. That didn't deter Cubs executives Theo Epstein and Jed Hoyer -- who had drafted Rizzo in the sixth round in 2007 when they led the Red Sox -- from envisioning Rizzo as their first baseman of the future.
Sixteen months later, the Cubs signed Rizzo to a seven-year, $41-million extension that included two team options as well, keeping him under club control through 2021. The contract has proved to be a huge steal for the Cubs, as they locked in a team leader and eventual three-time All-Star for years to come, a move that helped fortify the foundation of a team that would win the championship in 2016. One prominent agent estimated Rizzo cost himself around $150 million in the long term by agreeing to that deal instead of hitting free agency as soon as he was eligible.
"We know how much Anthony is worth to us on the field and in this clubhouse," third baseman Kris Bryant said.
Rizzo has never complained about his contract. When he signed it, he was a cancer survivor who had not yet produced a big season in the big leagues. Rizzo quickly came to embrace the city just as the fans embraced him, and he found comfort off the field as well, raising millions of dollars for cancer research and serving as a pillar in the community.
"When I signed the deal, I knew if I panned out to be who I thought I would be, I would be underpaid," Rizzo said. "I think in a couple of years it will probably even out if I continue to play the way I know I can play. I am set for life. I have a lot of money. Financially, I am OK. Everything else will be gravy on top of it."
Rizzo has been a model of consistency, hitting the 25-homer, 100-RBI plateau in each of the past four seasons. He has only missed a combined 23 games in the past four years and 47 in the past six seasons.
The question now is whether he'll play out his contract through 2021 and hit free agency at age 32 or reach an extension with the Cubs before then.
"I love this city and everything we have done here," Rizzo said. "The fans, the people, the hospitality we get in Chicago -- I feel like Chicago is home for me. Two more years after this year is the contract. Right now, I can never visualize playing for another team. Still, you can't be that naive as to how businesses are run."
Contract extension talks haven't been seriously broached by Rizzo's agent with the Cubs.
"There has been a little bit (of conversation)," Rizzo said. "There is nothing to where we are going to put pen to paper yet. Obviously, it is no secret I want to be a Cub for my whole career. It would be very special to do that. This, however, is 2019 and we all are focusing in on this season. That is the big picture."