He did such a good job that they figured they'd make him a more consistent contributor.
On Thursday, Schilling -- or "Curt In the Car," as they identified him when he randomly called in -- made his first in-studio appearance on the four-hour show, which starts daily at 2 p.m. ET. The 42-year-old recently signed a contract with WEEI in which he will be a regular contributor to the Web site and make in-studio appearances like Thursday's.
Schilling will appear on "The Big Show" one Thursday each month. On other Thursdays, he'll call into either "The Big Show" or "The Dennis & Callahan Morning Show" for a 20-to-30-minute segment.
The first thing host Glenn Ordway wanted to get out of the way during Schilling's debut was the constant gushing by callers over what he did through his four playing years with the Red Sox because, while Schilling values the kudos, he's there to talk sports.
With that out of the way, Schilling did just that.
Coming as no surprise to anyone, the first issue regarded the gaping hole the Red Sox currently have behind the plate -- one Jason Varitek has been filling for the past 12 years. Schilling was asked why he thinks the former captain hasn't re-signed with Boston yet.
"There's a lot of reasons," Schilling said. "I think [the Red Sox] went into this winter very intent on trying to find that catcher of the future. I think the plan was to offer 'Tek arbitration and have a trade made for a kid ... somebody to bring in for the next year or two, because I think that the initial plan was to offer [Varitek] arbitration. [They thought,] 'Of course he's going to accept it,' and then next year, they might be in this spot.
"I think they were going to start to wane the staff off of a Jason Varitek and onto the catcher of the future."
The market for the switch-hitting catcher, who turns 37 in April, has been down because teams would have to give up a first-round Draft pick to sign him, and he's coming off batting a career-low .220 in 2008.
But Schilling said Varitek's impact isn't measured through stats.
"I think you're looking at about $45 million invested in this pitching staff next year, and if your catcher doesn't work with your pitching staff, it's not one player that has a down year, an off season, it's potentially the entire staff," Schilling continued. "That might be overstating how many guys would have good or bad seasons based on Jason being back there, but I'm very comfortable with saying that there is very little chance that every guy on that staff won't be better if he's back this year. He's the kind of guy that makes you as good as you can be each start.
"Jason knows us as good, if not better, than some of us know ourselves."
Schilling also added that the Red Sox could face some danger if they rely on a young catcher to take the reins behind the plate and it doesn't initially work out -- especially if they trade away prospects like Clay Buchholz or Michael Bowden.
"They're going to know in Spring Training if it's not syncing up [with a young catcher]," Schilling said. "But it's too late at that point to do anything, because you've already signed this kid to be your catcher of the future. Now what happens if this catcher of the future comes on, takes on the No. 1 job, and he can't cut it the first month?
"My point is it's an irreversible mistake if you take that path."
Schilling also got into what happened with Manny Ramirez during the slugger's last season with the Red Sox. Schilling said Ramirez came into Spring Training last year in great shape and expecting an extension, but he got really frustrated when it didn't end up happening.
"People talk about the fact that he was here for eight years and everybody put up with it, [but] it wasn't like the things that happened, happened untouched," Schilling said.
"There were multiple teammates that had issues with Manny and confronted Manny. And the hard part was that, on Monday, Manny could be the kindest human being you've ever met in your life, and on Tuesday, it could be, 'I want out tomorrow or I'm not coming to the ballpark.'"
Schilling is currently a free agent and has expressed interest in wanting to pitch the second half of the season for a club. If he doesn't, he'll end his 20-year career with 216 wins, a 3.46 ERA, six All-Star appearances and three World Series rings.
Still, he doesn't believe that's good enough to put him in the Hall of Fame.
"I feel very good about what I was able to do, I'm very proud of my career," Schilling said when posed the question by a caller. "I did  years -- far more than I ever expected. But I played with Randy Johnson, I played with Pedro Martinez, I played with Dale Murphy. I played with guys that have [Cy Young Award] plaques. I'd like to think I did well. I'd like to think that, if I had a must-win game, the guys I played with would want me to have the ball. But no, I don't think I deserve to be in the Hall of Fame."
Alden Gonzalez is an associate reporter for MLB.com. MLB.com reporter Ian Browne contributed to this report. This story was not subject to the approval of Major League Baseball or its clubs.