Illustrations: Kagan McLeod

“We’ll see about his maturity level. That’s what I would question.”
–TONY DUNGY, former coach of the Indianapolis Colts, now an analyst with NBC, June 3, 2009

They were talking about the new Bears quarterback, the rocket-armed field general-cum-savior brought here to deliver the team from passer follies past, but it sometimes seemed the football pundits were scolding a teenager who’d blown curfew again. Was Jay Cutler “mature” enough to lead the team? Was he a baby? A brat? A whiner? In addition to Tony Dungy’s eyebrow-raising comments, there was ESPN’s analyst Mark Schlereth, blistering Cutler for his demand to be traded from the Denver Broncos: “You’re looked at as the biggest spoiled baby that has ever played in the franchise.” There was the Chicago sports talker Dan McNeil, writing in the Sun-Times when it became clear Chicago was interested in Cutler: “Big body. Big arm. Big dope.” And the columnist Gene Wojciechowski: “Will someone please give Jay Cutler his pacifier, hand him his favorite blankie, and put him back in his crib for his afternoon nap?”

So did the Bears trade for a quarterback or Lindsay Lohan?

“I’ve heard comments that he’s a whiner or a crybaby,” says Jay Burch, Cutler’s high-school athletic director. “I kind of laugh when I read all that, because anybody growing up with Jay who knows his personality, knows that’s about as far from the truth as you can get. Spoiled would be the last thing I would use to describe him.”

“I don’t see him as that type of guy,” agrees Cutler’s former Vanderbilt teammate Marlon White. “I don’t think he’s overly cocky and not easy to deal with. I feel like he’s confident and he believes in what he believes in. He knows what he knows and believes in it 100 percent.”

Devin Hester, Cutler’s new target at wide receiver on the Bears, told the Chicago Tribune in June that he had wearied of the baby talk. “If you haven’t been around a person like Cutler, how could you say something like that?” Hester said, referring to Dungy’s comments. “He’s calm in the huddle. He makes us laugh, and he jokes around before the ball is snapped. That’s the kind of quarterback who is relaxed and says, ‘Let’s play ball.’”

The Denver Post columnist Woody Paige, who followed Cutler closely during the quarterback’s three years in Denver, views the “M” word as one of those sports-talk buzzwords that analysts love to bluster about but that usually have no relationship to the athlete’s performance on the field. Dumping a bucket of Gatorade on a coach’s head isn’t exactly adult behavior, but who here wouldn’t like to see that in January?

“Yes, he’s immature,” says Paige. “So what? John Elway was immature. Michael Jordan showed signs of immaturity. . . . Tony Romo goes off to Cabo San Lucas with his girlfriend during the bye week of the playoffs. What kind of message did that send? [Cutler] hasn’t been arrested for drunk driving; he hasn’t been arrested in a bar fight; he hasn’t had a domestic abuse charge against him. So he’s a little immature. I don’t think that wears so badly.”

“Santa Claus’s favorite elf has been selected to play in the Pro Bowl, and he could lead his team to an NFL division title Sunday. Ho. Ho. Ho.”
Denver Post columnist WOODY PAIGE, December 19, 2008

About six hours south of Chicago, half a world away from the North Pole, in a rural corner of Indiana where the deer you find are not of the flying variety but the kind that flash before the headlights on dark back roads, lies the improbably named hamlet of Santa Claus. Home to the Santa Claus Candy Castle, Santa Claus Museum, and Holiday World & Splashin’ Safari, the little town of 2,200 was also the place where the Bears’ Christmas gift—Jay Cutler—was first unwrapped.

“Holly Park, that’s pretty much where I honed all my skills,” Cutler told the Denver Post in 2006, describing a playground near his childhood home in Christmas Lake Village. “Baseball, basketball, football. Every day after school, I was there.”

Legend has it that the town’s fathers originally wanted to call it Santa Fe, but the name had been taken by another Indiana town. In a moment of red-cheeked whimsy, the name Santa Claus was chosen in 1852, and soon the town and its post office were flooded each year with letters from children all over the world hoping for generosity from the Jolly One.

For Cutler, hailing from Santa Claus sentenced him to a lifetime of eye-rolling puns and a wearying need to explain. By his senior year at Vanderbilt, he had grown so tired of questions about his hometown’s peculiar name that he told a Nashville newspaper, “It could be named Easter Bunny for all I care.”

By all accounts, though, he loved the place and the life provided for him by his father, Jack—an Indiana state trooper with a concrete business on the side—and his stay-at-home mother, Sandy. It was there, as the oldest of three children (he has two younger sisters, Jenna and Joy), that he learned his work ethic, rising early to help his father pour concrete and tie rebar.

And it was in nearby Lincoln City, at Heritage Hills High School, that Cutler’s athletic gifts flourished. “Jay was a good athlete from day one,” says Jay Burch, the school’s athletic director. “He was playing at a totally different speed than kids play at in high school.”

Much has been made of Cutler’s failure to lead the Broncos to the playoffs in his three years there, and his inability to secure a bowl berth during his career at Vanderbilt—the implication being that he was not a winner. His high-school accomplishments, however, contradict that bit of logic. After taking over as the starting quarterback at Heritage Hills during his sophomore year, Cutler went on to lead the Patriots to a 15-0 record and a state championship in his senior year. He also starred in baseball and basketball. (“I don’t know how many dunks he had his senior year,” says Burch, “but it was an extraordinary amount for a six-three guard.”)

His reputation as a stat-padded star who couldn’t win big games has continued to dog him, however, all the way to Chicago. “Yeah, it bothers me,” Cutler told the Denver Post after the Broncos took him with the 11th pick of the 2006 draft. “But I’m over it . . . I know how to win.” Words the Bears hope to put a bow on.

“The guys respected him. He took a beating every week, but he played every game.”
–MARLON WHITE, Cutler’s teammate at Vanderbilt, in an interview with Chicago

The good news for Jay Cutler when he arrived at Vanderbilt in 2001 was that he would have a good chance to start as a freshman. The bad news was that he’d be playing for Vanderbilt. The school—a perennial patsy in the powerhouse Southeastern Conference—had not had a winning season in more than two decades, had not played in a bowl game since 1982, and could lay claim to exactly one quarterback selected in the first round of the NFL draft, a player named Billy Wade, chosen by the Rams, in 1952 (and remembered fondly by fans in Chicago for leading the Bears to the 1963 NFL championship).

Cutler did indeed start in his first year and every game after that at Vanderbilt. In fact, he became a star, setting school records for total offense, touchdown passes, passing yards, pass completions, and pass attempts.

His arm won over the fans. His toughness won his teammates. “He took a beating, right up until his senior year,” says White, who played wide receiver. “But he played every game. I mean, the Sunday after the games, he’d be beat up bad. So when everybody tries to talk down about how he’s spoiled, he took a pounding in the toughest conference in the country, every Saturday.”

In the NFL, questions have swirled about Cutler’s character, his ability to lead. Never among his Vandy mates. “He was willing to call guys out when they did something wrong,” recalls Trey Holloway, who played center for Vanderbilt. And they didn’t resent him for it? On the contrary, says White, “we appreciated it. We felt like that was him being a good leader, not being afraid to get on people for messing up. He demanded respect and he got respect.”

“People have no idea what I’m drinking or how much I’m drinking. I might have a beer and water the rest of the night.”
–JAY CUTLER, The Indianapolis Star, April 24, 2009

It wasn’t a pretty picture. Or photograph, rather. There was Cutler, freshly anointed savior of Soldier Field, caught on camera in mid-April hoisting a beverage next to that Bears bad boy Greg Olsen, eyes half-lidded and lips pursed in a classic “Dude, I’m so wasted” pucker. Whether Cutler really was plastered, or just the victim of one of those in-between-expression shots that can make even the sober look sozzled, the image stirred a frisson of, if not alarm, then apprehension into the city’s celebratory mood.

Addressing the issue at a press conference three days after the picture surfaced, the Bears’ general manager, Jerry Angelo, seemed more concerned about Cutler’s handling the blitz than being blitzed. “We know he goes out; we know he does those things,” Angelo told reporters. “I don’t think that’s a big thing at this point. It’s what he does on Sunday is how we’re going to evaluate him.”

Still, this was a man who only a year earlier had revealed that he had type 1 diabetes, a disease that doesn’t mix with highball revels. What’s more, Cutler was holding himself up as a role model for children stricken with the malady. For some, that didn’t go down well. “He’s a 25-year-old single guy living in Chicago, he likes to get out with teammates and enjoy some adult beverages. Why not, right?” the Indianapolis Star columnist Bob Kravatz wrote in April. However, “the photos have ended up all over the Internet, leaving people asking, ‘Is a diabetes spokesman supposed to be out pounding beers?’”

Rising to Cutler’s defense was a woman who had Twittered about Cutler’s visit to Hub 51 the night the offending photo was snapped. Julia Allison, a gossip girl columnist for Time Out New York, told that she had hung out with Cutler that night and that he’d downed a couple beers. “He was actually quite witty,” she told the blog. “Impressive given that he throws a ball for a living.”

Marlon White, a former teammate of Cutler’s at Vanderbilt University, laughed when I asked about Cutler’s nightcrawler rep. “Um, yeah. That’s legit. Flat out,” White told me. “He’s been like that since I’ve known him.” Wait—so Cutler is a big drinker? “No, no, I’m not saying he drinks a lot,” White says. “He just likes to go out, be on the scene. I’m just surprised that it’s just now becoming known.”

“The question is . . . whether he has a couple of beers, then drinks water or whether he drinks to excess,” says Woody Paige, the Denver Post columnist. “I haven’t followed him around, but I can tell you truthfully, based on people I know who went to places he went to, he didn’t get drunk or surly or out of hand.

“There’s not one mark against Cutler the whole time he was in Denver in terms of a police officer or somebody writing on the Internet that he was a drunk and knocking people around. He doesn’t have any [DUIs]—any of the old Charles Barkley stuff. The guy’s from Santa Claus, Indiana. That doesn’t make him an elf, but he’s not a bad actor.”

“I think it’s kind of funny now at this point, that I’m back here and now he’s here. Things happen for a reason, and I’m lucky to be here, and I’m excited to get to work with Ron.”
–JAY CUTLER, in a press conference introducing him as the Bears’ new quarterback, April 3, 2009

It was all set. Cutler, three-sport star and football god at the tiny Heritage Hills High School in southern Indiana, believed he had an offer to play for the University of Illinois, coached at the time by Ron Turner. “Jay had told us [about his decision] in early November while we were still in the playoffs,” recalls Heritage Hills’ athletic director, Jay Burch. “He hadn’t paid his official visit to Illinois yet, because you weren’t allowed to” until the season was over.

When Cutler finally did make his visit, he wasn’t expecting a red carpet—but he never imagined the reception he would receive. “All of a sudden there was no scholarship,” Burch says. Turner had rescinded the offer. The coach was going with a highly touted recruit from California named Mike Dlugolecki (who eventually transferred to San Diego State and is now out of football).

Cutler was crushed—and his father was angry. “It’s not right,” Jack Cutler told’s Pat Forde in April 2006. “I still have a bitter taste in my mouth over that.” By then, most schools had locked in their prospects. “Doors were closing,” recalls Burch. “Which happens when it’s December and you’re trying to open recruiting back up and February is signing day.” With the help of Cutler’s father, Burch assembled a highlight reel and sent it around the country. A couple of schools nibbled, but nothing materialized.

Down to his last option, Burch contacted Vanderbilt. “When I called, I couldn’t believe it. They hadn’t even seen the tape. I said to the guy, ‘You’ve got to be kidding. This guy’s a great player!’” The next day Vanderbilt offered Cutler a scholarship. “I think they watched the tape,” Burch says.

It was the best thing that could have happened, Burch says. After his Vanderbilt career, Cutler would become so coveted that Denver would draft him in the first round in 2006. And earlier this year, the Bears gave up a jaw-dropping two first-round draft picks to pry him loose from the Broncos. The twist, of course, is that the offensive coordinator Cutler will be playing for is the very same Turner who jilted him at Illinois.

“I have a stronger arm than John, hands down. I’ll bet on it against anybody’s in the league. Brett Favre’s got a cannon. But on game days, there’s nobody in the league who’s going to throw it harder than I am at all.”
–JAY CUTLER, quoted in Sporting News, October 9, 2008

Denver fans seemed to embrace Cutler’s cockiness—until he tugged on the wrong cape. To say John Elway, the big-toothed Hall of Fame quarterback who bazooka-armed his way to two Super Bowl titles, is adored in Denver is like saying a bronco likes to kick up its heels. Elway is the city’s patron saint. A demigod. Yet there was Cutler committing football blasphemy, claiming he had a stronger arm than The Duke.

Reactions ranged from incredulity to kudos for Cutler’s bravado to blunt outrage. “Oh Jay nooo. . . .” wrote one commenter to the Sporting News website. “You may even be right, but you just don’t say that in Denver. We will crucify you.”

“In my opinion, these guys should all have their mouths duct-taped shut until they actually win something other than their high school homecoming game,” added another.

 “It was hit or miss,” Cutler told the Rocky Mountain News after the comments ricocheted around the blogosphere. “Some people agreed, some people didn’t agree, and some people were upset with it. It caused a little stir.” But Cutler did not back down.

Some, like the Chicago sports pundit Dan McNeil, gave Cutler the benefit of the doubt. “Maybe Cutler’s cockiness can be passed off on youthful exuberance,” he wrote in the Sun-Times. “He didn’t say he was better than Elway. He suggested he had a stronger arm than Elway.”

Whatever the case, Bears fans may have to get used to such eyebrow-raising verbal fumbles. Fine. As long as the blunders are committed behind a microphone and not under center. If the team wins, its followers can be very forgiving of brashness in the quarterback. See Jim McMahon.

“This goes everywhere with me,” Cutler said, referring to a small pouch in front of him. “The first thing I do in the morning is test myself to see where I am, and it’s the last thing I do before I go to bed. This whole thing is a little scary sometimes, but it’s not like you have a choice. It’s part of your life, you know?”
–JAY CUTLER discussing his diabetes in an interview with Yahoo! Sports, May 16, 2008

He began to notice something wrong around October 2007. He’d been feeling tired, cranky, and irritable. Then he dropped eight pounds in a week. With each passing Sunday, he seemed to shed more weight. His passes lost their zip. He felt weak. By the last game of the season, Cutler “was down to about 202, 203 [pounds]” from 238, he recalled in an interview with the NFL Network. “It was tough. I lost a lot of muscle, a lot of strength throughout the season, and we didn’t really know what it was.”

In April 2008, a couple of weeks before his 25th birthday, the mystery was solved: Cutler was diagnosed with type 1 diabetes, the rarest and most serious form of the disease. Henceforth he would have to carry a finger-stick kit with him to monitor his blood sugar levels and would need daily insulin injections.

Hard as it was to hear, finding out “was a huge relief,” Cutler told the sportscaster Jim Rome early in 2009. “I went through a whole six-month stretch of not knowing what’s going on, losing all the weight.”

Cutler discussed the diagnosis on a Denver television sports talk show in early May 2008, and was asked the obvious question: Could he still play? The answer was, absolutely. The doctors “encouraged me that I could still play football and I could still be successful,” he said.

Soon after the diagnosis, Cutler announced that his Jay Cutler Foundation would help children with diabetes in addition to lending support to underprivileged kids.

Cutler isn’t the first professional athlete with the malady to play. Jackie Robinson had the disease, as did Bobby Clarke, the hockey Hall of Famer. A number of other football players have enjoyed long careers despite the same diagnosis, including the former Vikings Wade Wilson, a quarterback, and Jay Leeuwenburg, who played center.

That doesn’t mean it will be easy for Cutler. He will have to be hypervigilant about monitoring his blood sugar level. Even when carefully managed, the disease can cause long-term problems, such as kidney failure, blindness, and amputation. Ron Santo, the former Cubs great, has had both legs amputated in his long battle with type 1 diabetes.

“There’s certain days that you feel sorry for yourself,” Cutler told Rome. “Why did I get this? It’s tough to deal with it, but you’ve got to have a positive attitude about it. I’m put in a position; I have diabetes, and there’s a lot of kids out there that have diabetes. And hopefully I can be a good role model for them.”

“We’re not the best of friends. . . . I don’t like how he carries himself. I don’t like some of the stuff he does on the field.”
–JAY CUTLER, commenting on the San Diego quarterback Philip Rivers, on Best Damn Sports Show Period, October 2008

Cutler may have had the reputation for too much swagger, but it was another quarterback doing the smack-talking on Christmas Eve 2007. Cutler’s final fourth-quarter pass had barely fluttered to the turf in the 23-3 drubbing of the Broncos when the San Diego quarterback Philip Rivers stepped from the sideline—a teammate waving “Bye-bye” over his shoulder—and began taunting his counterpart. “Not exactly holiday cheer in the air,” the announcer, Mike Tirico, observed. “No, absolutely not,” the sideline reporter Michele Tafoya answered. “Grinches down here.”

Though Rivers initially caught most of the flak for the incident, evidence later suggested that Cutler hadn’t exactly acted with honor during the game.

The ESPN analyst Eric Allen said that Cutler had grabbed his crotch at one point in the game, and other sports talkers suggested that Cutler had done his share of jawing. “He is a punk,” declared the Chargers linebacker Matt Wilhelm. “Jay Cutler—he and Tony Gonzalez are the biggest crybabies in the league.”

Whatever the circumstances, the moment stuck to Cutler, yet another example of his supposed petulance. “Go away mad, Jay-C,” Mike Kiszla, a Denver Post columnist, wrote after Cutler was traded to the Bears. “It’s what you do best, whether feuding with San Diego Chargers rival Philip Rivers or feeling dissed by [the Broncos coach Josh] McDaniels.”

“I’m not pleased with it at all. . . .We had zero inkling this was going to happen. I hope it all works out. But I know I’m disappointed; I’m not happy."
–JAY CUTLER, commenting on the firing of Mike Shanahan, the Broncos’ head coach, in the Rocky Mountain News, December 31, 2008

Cutler was shocked. Then angry. Then concerned. Mike Shanahan, the winningest coach in Denver Broncos history, the man who had helped develop the quarterback John Elway into a legend and was perhaps Cutler’s biggest ally in town, had been fired.

Less than two weeks later came the next jolt. Shanahan’s replacement, Cutler learned in a voicemail from the Broncos’ owner, Pat Bowlen, was Josh McDaniels, a 32-year-old offensive coordinator from the New England Patriots, a man who had no head coaching experience.

The good news was that McDaniels was an offensive specialist, and the Broncos’ biggest needs seemed to be on defense. Therefore, whatever big changes lay in store would involve the defense, not Cutler.

Bothered as he was, the young quarterback seemed willing to give McDaniels a chance. “He’s very energetic,” Cutler told the Rocky Mountain News in late January after chatting with McDaniels. “When I got off the phone, I was excited. Just talked to him about the importance of our relationship.”

But then the bomb exploded: McDaniels, it turned out, was discussing a three-team trade that would ship Cutler elsewhere and replace him with New England’s Matt Cassel, who had flourished under McDaniels’ tutelage as a replacement for the injured superstar Tom Brady.

“McJaygate,” as the Denver media called it, was born. By now, the general plot of the soap opera is known: Cutler and McDaniels meet. Cutler doesn’t like what he hears. Cutler’s agent, Bus Cook, demands a trade. Cutler doesn’t show up for McDaniels’ first team meeting. McDaniels insists the team is “committed” to Cutler. Cutler stops answering McDaniels’ calls. Bowlen unloads Cutler to the Bears. Cutler and McDaniels never speak again.

Denver seemed divided on who was to blame. Some faulted Bowlen and McDaniels, saying they deeply disrespected one of their most valuable players for no good reason. Others pointed at Cutler, calling him everything from oversensitive to a spoiled brat.

Left behind in the aftermath was a question: Why would a team get rid of a quarterback like Cutler if there wasn’t something wrong? Why would the Broncos even entertain the notion of another quarterback if Cutler was so great?

The Denver Post’s Woody Paige tells me that he thinks it was a classic grass-is-greener blunder. McDaniels, he says, loved Cassel. When someone from New England told him Cassel might be available, he was intrigued. “It’s a bad analogy but it’s all I can come up with,” Paige says. “You’re in love with your wife and all of a sudden you meet Miss America and you go, ‘Well, at least I’ll talk to Miss America; I might leave my wife for Miss America.’ But then you find out that Miss America already has a boyfriend and your wife finds out that you’ve been hustling Miss America.”

McDaniels, as often happens to those engaged in such monkey business, wound up with neither. Cutler, whose wounded feelings forced Denver’s hand, wound up with the Bears. Cassel is now wed to the Kansas City Chiefs. Denver's new beau is Kyle Orton—the Bears’ signal caller last year and, though competent, few teams' idea of Miss America.

How the soap opera will ultimately play out—whether Chicago falls for Cutler, whether Cutler makes Denver regret the breakup—will be determined on the field.

Meanwhile, Cutler has adopted a tone apropos of a messy divorce. “I’m sure I would do things different, they would do things different,” he told the Chicago media at his first press conference here. “The bottom line is, I'm a Chicago Bear. . . . Hopefully over time I can win everybody over.”