They could start with the anemic offense that just couldn't deliver in the clutch. The Rays led the Majors with 1,193 runners left on base and scored just 612 runs, fewest in the American League. Their .247 team batting average was the lowest in club history. The Rays were shut out 18 times.
To put it bluntly, ever since this regime took over in the mid-2000s, the Rays have been the model for a small-market, low-revenue franchise.
But as Maddon, one of Major League Baseball's most respected managers, said, "It was such a weird season to describe. We were 18 under .500, then got even -- that's 18 games over .500. You have a winning record on the road, a losing record at home. How did that happen? I have no idea.
"And look at the records the pitching staff set this year."
Then, he used football terms: "We just had to score more points. A lot of that had to do with being bad in the red zone. We got inside the 20 a lot [runners on base], but we couldn't score.
"It was just a weird, awkward season. You had to be there on a nightly basis to witness it. It was a strange year, people on base we couldn't drive in -- all kinds of awkward things that occurred; we have to figure out why in Spring Training."
This was supposed to be a banner year for Tampa Bay. The Rays were expected to go deep into the postseason, maybe make it to their second World Series.
And even when they were 18 games under .500 at 24-42 on June 10 with MLB's worst record after a 1-14 stretch, Maddon predicted they'd turn the season around.
He looked like a genius on Aug. 15 when they climbed to .500 at 61-61. From June 11-Aug. 15, they were 37-19, best record over that span in the Majors.
But the wheels soon fell off.
"We've gone through rough stretches over the last five-six years," said Friedman. "For the most part we just kept doing what we did -- win more games and be in the position we expected to be in.
"There was some sense things were going to work out this year, that we'd win more games just by virtue of the talent we had. All of us expected, 'Hey, we're just going to start winning games. We're too talented not to.'"
It just didn't happen.
Third baseman Evan Longoria, the team leader, told reporters he felt the players began the season with a mindset that "things are going to be easier than they really are.
"We all need to take a look in the mirror this offseason and understand what kind of players we are and be able to come back next year and try and fill those obligations -- what we're expected to do offensively, individually."
Now, Friedman, Maddon and Co. must sit down, dissect the debacle that was 2014 and convince themselves that the group of core players presently on board has the talent and motivation to return the Rays to contender status.
Friedman said tweaking the roster, probably through trades, is the early plan.
Maybe the envious model the Rays have built that propelled them to the postseason four of six seasons prior to 2014 has played itself out.
And maybe it's unrealistic to believe a franchise with such a low payroll can continue to compete with the big spenders -- no matter how astute those who run the franchise are. Their Opening Day payroll of $77.062 million ranked 28th among the 30 teams.
"It's kind of a cliche, but it's us against the world," offered Friedman, who added everyone in the organization shoulders the blame. "We're going into Spring Training next year with what I would imagine would be much lower expectations than this year.
"We love that. We'll go in and talk about how everyone is picking other teams ahead of us. This is all about what we can learn from this season that will help us go forward. That's where all our focus will be."
Even when the Rays won 17 of 23 games for the AL's best record in July, I felt the offense was a glaring weakness, certainly not potent enough for slug it out with the Orioles, Blue Jays and Yankees.
The Rays had always turned Tropicana Field into a devil's den for opponents, but in 2014 they were 36-45 at home, compared to 41-40 on the road.
Despite his uncanny positive outlook, in Maddon's most private moments he had to wonder if this team could turn the season around.
I asked him just that on Tuesday.
"I thought once we got back to .500 we had a legitimate chance, at least for the Wild Card," he said. "Early on, it was tough. We have never really gone on a 1-and-14 gig before. And to look up and see you're 18 games under .500, that's a really bad feeling.
"I had my one team meeting about a month before the All-Star Game and stated our No. 1 goal was getting back to .500. The night we got there it was pretty festive and I felt good about the whole thing. I thought there was a good shot, but we used so much emotional energy.
"Retrospectively, I thought we could do it, but realistically it's hard to maintain that kind of emotion to dig out of that kind of a hole and then get 15 games over .500."
And several weeks after reaching .500 (the Rays lost eight of their next 12 games), Maddon realized "this is going to be much more difficult than I thought."
Friedman put it this way: "We're obviously disappointed with the way this season turned out. We have the core talent in place for next year to be really, really good. Now we have to spend time tweaking the roster and focusing on different aspects of it to break camp next year with a realistic chance to be playing competitive games in September."
Friedman used the analogy of spending a lot of offseason time "looking under the hood."
If an overhaul isn't needed, a tuneup is obviously a necessity.