The day after new pitching coach Jim Hickey went on the team's flagship radio station and told WSCR-AM 670 that he would recommend the free agent to Theo Epstein's front office – "I would say, ‘Go ahead, good job, yeah, I'm onboard' – Cobb appeared on MLB Network Radio and sounded ready to follow Maddon to Chicago.
"As much of an honor as it is to be given a qualifying offer," Cobb said Friday, "to hear your name floating around (in) rumors with potential teams, and the magnitude or the (reputations) that some of these teams have for success, year in and year out, even the smallest inkling or the thought that they want you is even more of a humbling experience.
"I don't hide the fact that I've got the most respect for Joe Maddon and what he did for me coming up as a player. Not so much as a pitcher on the mound, but as a professional athlete and a professional baseball player, and how to deal with the mental side of the game. And how to deal with the stresses that come with a big-league lifestyle.
"There's nobody better in the game to control (that) and deal with people."
Cobb is expected to decline the one-year, $17.4 million qualifying offer from the Rays, tipping his hand by telling MLB Network Radio: "You're talking about, hopefully, a decision that's going to impact the next five years of your life."
That framework sounds a year or two too long for a guy who underwent Tommy John surgery on his right elbow in 2015 and has never made 30 starts in a season or come close to reaching 200 innings. But Cobb just turned 30 last month, has only 700 innings on his major-league odometer and went 12-10 with a 3.66 ERA and a Gold Glove nomination this year.
Hickey can help fill in the blanks for the Cubs because he was there for Cobb's rise through the Tampa Bay system, injuries issues and recovery process.
"I can't say enough good things about him," Cobb said. "He's become – not only a pitching coach – but a real close friend of mine. Obviously, if we move down the line and we're able to have some discussions with them, I'd be very honored to be able to talk with them and hopefully come to a deal."
In the same way that Maddon may have gotten restless managing the small-market Rays, Cobb sounded eager to play for the kind of built-to-last team that won the 2016 World Series and advanced to the National League Championship Series in three consecutive seasons.
"You kind of make a ranking system of what is most important to you and your family," Cobb said. "No. 1 and foremost – and me and my wife are both onboard with this – is that we're going to go to a place that we feel is going to be winners for the length of the contract.
"I've been through both. I've been through losing seasons and I've been through winning seasons. And the amount of joy that winning brings to us – it can't be replaced by a dollar figure."