Lester: Trade to Oakland made it easier to leave Boston

When the Boston Red Sox gambled by trading Jon Lester to the Oakland Athletics at the deadline, they took a calculated risk. 

Dealing his expiring contract to a team that wouldn't be able to re-sign him, the Red Sox firmly believed they could retain the three-time All-Star due to his desire for familiarity over money. 

That idea appears to have backfired as Lester addressed the media Monday in his new Chicago Cubs jersey - emblazoned with a new No. 34 - and said that the trade to Oakland opened his eyes and showed him that moving to a different organization wasn't all that bad. 

"I think so," Lester said of whether being traded impacted his approach to free agency, via Rob Bradford of WEEI. "We were traded. That was the unknown of going to a whole different coast, a whole different organization, a whole different philosophy. I think going there prepared us for this time. 

"I think if we finished out the year in Boston and you get down to this decision, I think it would be a lot harder. Not to say it wasn’t hard as it was, but that broke that barrier of, 'I wonder if I can play for another team.' I think we answered those questions."

Lester still acknowledged that it wasn't an easy decision to leave Boston - a place where he was part of two World Series championships - and the final choice came down to the wire. 

"We made it literally hours before it was announced." Lester said regarding his choice to accept the Cubs' five-year, $155-million offer. 

Lester spoke of his excitement to be reunited with former Red Sox general manager and current Cubs president Theo Epstein. He also said that he signed with Chicago because he believes the team is ready to win now. 

"I wouldn't be here if I didn't think we could win in 2015," Lester said. "I don't like to lose."