Harry Caray is smiling. Gazing down through outsized specs as a sign on a bar's rooftop high above Sheffield Avenue, the late, legendary baseball broadcaster looks as if he's seeing history in the making. Which he is. For on this cold and sunny October morning, Caray's beloved Wrigley Field is finally getting the face-lift it so desperately needs. If all goes well, the Chicago ballpark where Babe Ruth called his home run shot in 1932, where Ernie Banks smacked his 500th in 1970, where hope and heartbreak spring eternal, will look and play better than ever. So, even, might its famously cursed team (and Caray's longtime employer), the Chicago Cubs. The last time the Cubs clinched the World Series was in 1908. As Harry might exclaim, "Holy Cow!"

America's second-oldest major-league ballpark (after Boston's Fenway) and the Cubs' home since 1916, Wrigley took its name from chewing gum magnate and baseball maven William Wrigley Jr. Years later, Banks, who played both shortstop and first base from 1953 to 1971, dubbed Wrigley the "Friendly Confines"—a nickname that sticks today. But after field-pummeling rock concerts and a turf-torching fungus wreaked havoc on the grounds last summer, that cheery handle grew somewhat less apt. Wrigley has long been a fine place for watching games—what with ivy-covered brick walls, an old-fashioned, manually operated scoreboard and celebrities singing (or, in former Bears coach Mike Ditka's case, bleating) of peanuts and Cracker Jack during festive seventh-inning stretches. Increasingly, however, it was less swell for playing baseball—especially in right field, where the uneven surface caused ground balls to take odd, potentially error-causing hops. Sight lines from both dugouts were less than ideal too, courtesy of a pronounced "crown" that obscured the feet of infielders and made outfielders appear as floating torsos. Not to mention the field's rain drainage system, which hadn't been upgraded in decades.

Fortunately, the nation's top diamond doctor makes house calls. And he just happens to work nearby. His name is Roger Bossard and he's the head groundskeeper for the Chicago White Sox—yes, the Cubs' crosstown rivals. But his athletic affiliation matters less than his track record. In 1984, a member of the Saudi royal family hired Bossard to build the first-ever natural-turf soccer field in the desert. Accepting the challenge with typical brio, Bossard filled two jumbo jets with California sod and squired them overseas. With the help of a desalination unit to rid the grass of salty sand and a double-irrigation system to provide plenty of water, he succeeded in working a minor miracle. And while the Professional Golfers' Association, the National Football League and various American soccer clubs have also availed themselves of his services, baseball has been his true passion. No fewer than 10 of the last 16 major-league fields—several constructed from scratch, some extensively refurbished—are Bossard's handiwork. More impressively, five of the last seven World Series champs—the St. Louis Cardinals, the Arizona Diamondbacks, the Boston Red Sox (twice) and Bossard's very own White Sox—rose to glory on his state-of-the-art surfaces.

The Cubs could use some of that mojo. They know what any serious student of baseball knows: a top-notch groundskeeper is much more than a grass-cutting, dirt-digging laborer. He's a true craftsman and a crucial asset who must keep his field impeccably maintained. Above all else, the players crave consistency. "The thing that bugs them more than anything is if one day it's a brick and the next day it's soft," Bossard says.

So on this October morning, the "Sodfather" digs deep into still-soft dirt with a shovel. Nearby, bulldozers plow acres of sod into an ever-rising mound. Brontosaurus-size backhoes rumble in to clear 9,000 tons of earth. Next, Bossard begins laying out his patented drainage system: specially designed pitched and perforated pipes nestled in pea gravel topped by sand and blanketed by sod (in Wrigley's case, a heat- and humidity-resistant four-blend bluegrass from Colorado). The pure sand bed allows for proper gas and air exchange, which promotes optimal grass growth. (It also creates a desirable cushioning effect for the players.) Perhaps most important, Bossard's design prevents all but the most insistent game rainouts by quickly forcing water into a main, 12-inch "exhaust" vein feeding a large basin that empties into the city's sewer system. (In other, newer ballparks, he has installed as many as five veins, larger in diameter.) On a Bossard field, roughly 20 minutes after a downpour, it's "Play ball!"

Now in his 42nd season with the White Sox, Bossard, 59, has toiled in sod and soil since his teens. He studied agronomy at Purdue University but walked away from a college degree when he was offered a groundskeeping job at old Comiskey Park on Chicago's South Side. Over the years his calling has become his self-admitted obsession—one that rousts him from bed to plot and fret and keeps him road-bound for months on end. "I'm not a control freak at all," he says, "except for in my industry." While he's also a proud father and devoted husband, his go-go schedule leaves little time to spend with his wife of 19 years, Geri Lynn, and their two children, 17-year-old Brittany and 10-year-old Brandon. Consequently, he misses occasional birthdays, some Thanksgivings and more Little League games than he'd like. "That does bother me," Bossard says. "But I am from that old school. Certainly, I love what I do, but I also have to provide for the family, and that's what I do."

Roger Bossard is the inheritor of a groundskeeper dynasty. From 1936 to 1961, his Swiss-born grandfather Emil groomed League Park and Cleveland Municipal Stadium for the Cleveland Indians. Roger's father, Gene, was, at 22, the youngest head groundskeeper in the Major Leagues when he joined the White Sox at Comiskey in 1940. (Nearly 50 years later, Comiskey would be torn down and rebuilt across the street before assuming a new name, U.S. Cellular Field.) Gene turned the job over to his son in 1983.

Since then, the family legacy has rested on Roger's slight, strong shoulders. "There is an awful lot of pressure when you strive for perfection," he said in a 2002 interview. After a rock concert and other non-baseball events at the Cell (as it's commonly called) in 2006, White Sox Chairman Jerry Reinsdorf says, Roger came up to him wringing his hands. "He says, ‘It's really bad for my grass,'" Reinsdorf recalls. "He said to me, ‘How would you feel if a herd of elephants were to run over you?' I says, ‘I wouldn't like it very much.' He says, 'Well, that's how my grass feels.' The grass is a living thing to him."

Bringing the living carpet at the Cell to its striped and verdant apotheosis in 1990 led, Bossard says, to two anxiety attacks that felt like coronaries. Accordingly, he coddles the field like a nervous father. "We were playing the Yankees and Roger Clemens was warming up in right field and he wasn't pitching," former White Sox pitcher and current sports announcer Ed Farmer remembers. "And Roger went out there and said to [Clemens], ‘I'd like you to stop throwing here because you're digging up my outfield.'" Clemens left.

Such fierce turf territoriality notwithstanding, Bossard is actually more partial to his dirt than his grass. After all, he says, it's where 70 percent of the action takes place. So fond was he of old Comiskey's infield clay dirt that, before the crumbling stadium was razed, he filled trucks with 550 tons of it (which included the scattered ashes of several die-hard Sox fans) to build his field of dreams at the Cell.

There, assisted by a small crew, Bossard does much of the mowing, fertilizing, watering, sodding, rolling, raking and edging himself. During an hours-long process that precedes every home game, each position on the infield is repeatedly wet to suit each player's preferences (hard, soft or in between). Wielding an inch-and-a-quarter hose like an artist, Bossard adds brush strokes of water to a diamond-shaped canvas. For the third and final application, he screws on a misshapen brass nozzle that once belonged to his father. Hammer-pounded at the opening to produce a fine mist, its functionality is surpassed only by its sentimental value.

Among baseball insiders and fans, it's commonly believed that Bossard (like other groundskeepers) puts his talents to devious uses. "If the visitor's bullpen mound is not the same as the main mound, say it's just an inch off as far as the drop, it literally might take the opposing pitcher three batters, four batters, maybe an inning to adjust to the drop," he told Chicago Public Radio last year. "Now, once again, I would never do anything like this. These are things that I've heard of."

Perhaps at the dinner table. Grandfather Emil, who became known as the "evil genius of groundskeepers," was a whiz at what is euphemistically called maximizing the home field advantage. Over time he honed several techniques, including tilting base lines in or out so balls rolled fair or foul, digging up or tamping down base paths to prevent or abet stealing, leaving grass long or clipping it short to slow or speed grounders. He also moved the outfield fences back 12 to 15 feet to stymie the home-run-slugging Yankees. By and large, his tricks were employed selectively to bolster home team strengths and take advantage of opponent teams' weaknesses. And just about everyone, even superstars, fell victim. Years after his 56-game hitting streak ended in 1941, Joe DiMaggio remarked that Emil and his sons had helped ruin the run. "The Yankees hated to come [to Cleveland]," DiMaggio said, "because our every defensive flaw was exploited by the Bossards the way they prepared the playing field."

Emil's contributions were so critical that Indians manager Lou Boudreau called him "the tenth man in our lineup." The stellar condition of Emil's field, combined with his surreptitious diamond doctoring, facilitated more than a few Tribe victories. "I wouldn't be surprised if [Emil] helped us win as many as ten games a year," Boudreau told Baseball Digest in 1955. During Emil's tenure, the team won the World Series in 1948 and a pennant in 1954.

By the time Emil died, in 1980, Gene had presided over Comiskey Park for 40 years without witnessing a World Series trophy in White Sox hands—the result, some said, of a curse the team suffered following the "Black Sox" gambling scandal of 1919. But it wasn't for lack of trying. More than a few players were grateful for Gene's efforts. All-star Sox second baseman Nellie Fox was a better bunter thanks to raised base lines. Those who needed speed, such as Sox sprinters Luis Aparicio and Minnie Miñoso, found a bit more pep in their steps on Gene's extra-firm base paths.

And, like his father, Gene was a master at tweaking the terrain. Opponents lost their footing on tractionless mud, grounders fizzled on shaggy grass and bunts went foul when they should have gone fair. Among Gene's most cunning inventions was an infamous bog near home plate that came to be known as "Bossard's Swamp." The quicksand-like patch of dirt slowed ground balls that were hit off the Sox's low-slung, sinkerball pitches.

Roger's initiation into the family business began early. "Every Christmas, every Thanksgiving, when all the family [got] together, all the kids—we're always hearing my two uncles and Grandpa and my dad talking about players, different teams, different soils, different grasses, different fertilizers, what new technique can we come up with," he recalls. "At the time, you don't realize it's embedded in your mind. Then all of a sudden, at 14 or 15, Dad says, ‘Can you come down Sunday, the team's out of town, and give me a hand?'"

Roger officially came on board (part time, at first) during the 1967 pennant season. After waiting nearly four decades for a World Series title, he came down with the flu after the White Sox finally won in 2005 and couldn't attend his team's victory parade in downtown Chicago. He was, however, the first to get a diamond-encrusted championship ring (even before the players) when fans packed the Cell to celebrate. Except for the birth of his two children, he says, the post-series honor was "the greatest thing that ever happened to me."

On a cloudy and cool morning in late November, Wrigley's face-lift is complete. But is the team worthy of its new field? "I can't say I want the Cubs to [win a World Series]...obviously being a Sox person," Bossard confessed to Chicago Tribune reporter Paul Sullivan. "Let's just say I hope the Cubs are in it next year, playing us."

Meanwhile, Bossard has begun to think of hanging up his hose—or at least cutting back, in eight or nine years. "There's no way I could hit a light switch and just shut it off," he says. And if Brandon, his 10-year-old son, wants to continue the family business, that would be just fine. Bossard pére has already seen early signs of interest. "This past year I take him out [to the Cell] and we play catch, I hit him fly balls and then I do some of the work I need to do," Roger says. "And doggone if he doesn't grab the hose and I don't tell him a thing. I gotta tell you, it almost brought a tear to my eye because it brought me back to when I was a kid."

Mike Thomas, a staff writer for the Chicago Sun-Times, has written for Esquire and Salon.com.
Chicago-based photographer Tim Klein specializes in documentary and portrait photography.