Recently, Rogers Sportsnet aired a major sporting event in Toronto. The reaction lit up the Internet. Live-tweeting. Breathless podcasts. For a few glorious days, championship fever gripped the Tdot.

Any fan base worth its salt loves nostalgia, making Rogers’s decision to re-air the 1992 World Series a great call under any circumstances. On Sunday, Rogers doubled down by showing Game 1 of the ’93 World Series, and will air the other five games over the next five weeks. Still, watching Jimmy Key, Kelly Gruber, and Tom Henke jump into a dog pile — or, spoiler alert, Paul Molitor, Dave Stewart, & Co. mobbing Joe Carter a year later — takes on a different tone than seeing the ’98 Yankees or even the ’03 Marlins celebrate. The ’92 Jays made history by celebrating the first World Series in Canadian baseball history, then the ’93 club became the first team to repeat since the dynastic ’70s made back-to-backs commonplace. But rewatching that mulleted, Braves-whacking bunch, then Joe Carter’s finest moment, Jays fans can’t help but feel more than nostalgia. Because for Jays fans, and Toronto sports fans in general, the past 20 years have been a nuclear wasteland.

The year of the Jays’ second straight World Series also marked the first season of a stretch that brought 10 playoff appearances and four conference finals in 12 years for the Maple Leafs, but those seasons usually ended in heartbreak which is still better than seven years and counting without a return trip to the postseason for one of the NHL’s biggest-banking franchises. The Raptors made their debut two years after “Touch ’em all, Joe!” and have been awful most years since then, with a couple of brief, mild spurts of success mixed with 12 losing seasons. But the Jays have been the worst of the bunch only the sad-sack Royals and Pirates have gone longer than the 20 years since the Jays’ last playoff berth.

Now, thanks to a flurry of offseason moves, the Jays have inspired more confidence, more hope, more sheer giddiness in their fans than they have in two decades. The journey to this point — from repeat champion to perennial also-ran back to beacon of optimism — has featured so many mistakes and pitfalls that they deserve several distinct categories, many of them offering lessons for the AL East favorite 2013 Jays and their architect, GM Alex Anthopoulos.

The Rich and Prosperous Toronto Blue Jays

Lauded for years as a model franchise with a top-notch farm system, it took a Yankees-style spending spree to push the Jays over the top in ’92 and ’93. It seems crazy to imagine now, but two decades ago, Toronto became the first club to trot out a $50 million payroll, while paying more in revenue sharing than any other team. After winning three division titles in seven years on the strength of younger, cheaper talent, the mantra became “win now.” In August 1992, the Jays traded Jeff Kent and Ryan Thompson for David Cone; Cone was one of the league’s elite pitchers in his prime, but the then-24-year-old Kent would go on to have a Hall of Fame–caliber career, albeit one most wouldn’t have predicted back then. The Jays also splurged for an army of veteran free agents, including Jack Morris, Dave Winfield, Paul Molitor, and Dave Stewart, and picked up Rickey Henderson at the ’93 trade deadline.

In later years, an overarching sentiment would emerge, one that claimed top free agents would only come to Toronto if the Jays outbid the rest of the league by a wide margin. But back in the championship years, the Jays were a marquee attraction. Playing winning baseball and becoming the first team to draw 4 million fans in a single season thanks to SkyDome’s relative new-stadium smell, the Jays were winning, and they were loaded.

The Strike That Hammered Canadian Baseball

When the players went on strike on August 12, 1994, the Montreal Expos owned the best record in baseball. The lost revenue from the rest of that season (and postseason, assuming they’d hold on to play in October), combined with a hideous fire sale the next spring, walloped fan and corporate enthusiasm in la belle province (which had already been shaky before the Expos’ renaissance under manager Felipe Alou), dealing a crushing blow to the franchise. Ten years after the strike, the Expos were gone, bolting for Washington, D.C.

It would be a stretch to say that the strike hurt the Jays as badly as it did the Expos — after all, Toronto still has a team. But as author Jeff Blair details in his upcoming book, Full Count: Four Decades of Blue Jays Baseball, the Jays were below .500 when the strike hit, but they still led the league with more than 2.9 million fans drawn and seven weeks yet to play. Maybe the team wasn’t destined for sustained greatness, given that their average age was one of baseball’s oldest at a tick below 30 during their World Series years, and that the Yankees were assembling a juggernaut team, one that would forge the sport’s most prolific dynasty since the Big Red Machine.

Still, the strike dented the team’s World Series afterglow. When baseball decided to start spring training using replacement players, Jays management bristled at the notion, for both philosophical reasons and because Ontario labor laws threatened to make games using scabs impossible. As a result, the Jays did essentially no marketing at the start of the ’95 season. They still drew 2.8 million fans in an abbreviated season. But that dropped Toronto to third in the American League, starting a long, steady decline in attendance and overall fan interest that the Jays are only now starting to overcome.

The Exodus

One by one, key figures from the Jays’ World Series years disappeared. The team’s architect, Pat Gillick, left in ’94, only to reemerge in 1996 with Baltimore, right before the O’s reeled off two straight playoff berths. John Olerud went from an impossible .363/.473/.599 line in ’93 to posting merely good numbers three years later, fueling a trade to the Mets for the immortal Robert Person. Roberto Alomar left to go play for the Orioles. That same offseason, Devon White, starter of the second triple play in World Series history and overall defensive wizard, ditched Toronto to sign with the Marlins.

Departures happen all the time, especially on championship teams. The only danger, actually, is that management gets complacent and doesn’t try to bring in new blood. But in Olerud and Alomar, the Jays lost two stars in their prime, with nothing but draft-pick compensation to cushion the blow. They were starting to develop a new wave of talent, with Shawn Green and Alex Gonzalez earning starting roles in their age-22 seasons, and Carlos Delgado also emerging. But the ’95 Jays still finished tied for the worst record in baseball, with the young hitters still a few years from developing into quality major leaguers and the farm system failing to produce front-line pitchers (other than Pat Hentgen), a problem that would eat at the team until the emergence of Roy Halladay a few years later.

The Rocket and the War Veteran

To make up for that pitching shortfall, the Jays signed Roger Clemens to a four-year, $40 million contract. In terms of straight bang for the buck on a player, the deal still ranks as one of the greatest free-agent scores in history. In 1997, his first year in Toronto, the Rocket led the AL in wins, ERA, complete games, shutouts, innings pitched, strikeouts, and Wins Above Replacement (11.6!), winning Cy Young honors in a rout. The next season, he led the circuit in wins, ERA, strikeouts, hit rate, and home run rate, pulling down a second straight Cy Young trophy. The ’97 team couldn’t do anything with Clemens’s near-historic season, with the Jays handing far too many at-bats to last-legs veterans like Otis Nixon and Joe Carter. Toronto fared much better in ’98, though: Delgado became a star, swatting 38 homers and hitting .292/.385/.592, Green launched 35 bombs of his own, and a fully Hulked-out Jose Canseco blasted 46.

The team’s homer barrage aside, many observers credited new manager Tim Johnson’s inspirational style for the team’s improvement in ’98. His favorite motivational tactic was to tell stories of his time in Vietnam. Too bad none of it was true. Johnson served in the Marine Corps Reserve during the war, but never made it to the battlefield. One can debate how much a manager influences any team one way or another. But the revelation of Johnson’s lies certainly created a sideshow, with several players distancing themselves from the manager and ultimately going elsewhere the winter after the ’98 season. One of those players was Clemens, who earned a trade to the Yankees for David Wells, Homer Bush, and Graeme Lloyd, a deal that would eventually lead to Suzyn Waldman’s finest moment.

The Division of Death

In winning 88 games in 1998, the Jays finished a stupefying 26 games behind the Yankees, who rolled to a 114-win season. Toronto also finished four games behind the Red Sox in the wild-card chase, meaning they had nothing to show for their best season in five years. This would become a common occurrence on Blue Jay Way. The Yankees have now made the playoffs in every year but one since the ’94 strike; the Red Sox famously broke their 86-year drought by winning a World Series in 2004 and then another in 2007. Even the sad-sack Rays would eventually lap the Jays, going worst to first in 2008 and making the postseason twice more since. Playing in a brutal division and dealing with a cruel, unbalanced schedule, Toronto won 84 games in 1999, 83 in 2000, 86 in 2003, 87 in 2006, 83 again in 2007, 86 again in 2008, and 85 in 2010, and got nothing to show for it save for a bunch of third-place finishes and a city full of increasingly indifferent fans.

In a weaker division, maybe a couple of those seasons would’ve netted playoff berths and some organizational stability. Instead, the Jays blazed through four managers in seven years following Cito Gaston’s firing in 1997. And when Gord Ash’s six-year tenure failed to move the needle, the Jays began a far-reaching search for a new GM, with a list that included names such as Terry Ryan, Billy Beane, and Paul DePodesta. The man who would eventually land the job, J.P. Ricciardi, would learn some hard truths about the value of timing.

Scouts? Who Needs ‘Em?!

One of the enduring images of Moneyball (both book and movie) is Michael Lewis’s caricature of the old, incompetent scouts sitting across the table from Beane and DePodesta, lusting after players with “the good face.” Ricciardi, then the director of player personnel for the A’s, didn’t speak critically of scouts in the book the way Beane, DePodesta, and Lewis did, and with good reason: He was a scout himself. Still, Ricciardi certainly benefited from the low-budget A’s success in earning the GM job in Toronto. And his mandate became clear pretty quickly: Find a way to win on the cheap here the way you did in Oakland, only this time do it with the filthy-rich Yankees and Red Sox in your division. Despite Ricciardi’s own scouting background, he took his marching orders to heart, slashing personnel within the first few months of being hired, including a passel of veteran scouts.

Ricciardi brought more changes during his first draft with the Jays, in 2002. Though the general manager is never the one who actually makes the picks during the draft — with some not even in the room after the first few rounds — Ricciardi told his rebuilt scouting staff what he wanted: college players, and lots of ’em. The idea made sense in theory. The A’s had started to find success going that route, as they sought players with better odds of making it to The Show. Problem was, Oakland was going all out with that strategy, and other teams were starting to take notice. The 2002 draft became known as the Moneyball draft, with the A’s taking a total of seven college players in the first round and sandwich round, and an incredible 23 college players in a row before their first high school pick. So when the Jays took just five high school players in the first 20 rounds of the 2002 draft, just two in the first 20 rounds in 2003, then just one each with their first 20 picks in 2004 and 2005, they were deploying a practice that left them behind the curve, chasing other teams who’d done it for longer, and more effectively. There simply was no market inefficiency to exploit anymore.

Outside factors conspired to make things worse. Then-Jays president Paul Godfrey lobbied commissioner Bud Selig for league assistance in defraying the exchange rate between the U.S. and Canadian dollars, one that was making it increasingly difficult to pay players’ salaries in American currency while bringing in weaker Canadian bucks for local revenue. Sure, said Selig. Just promise not to pay over slot for draft picks and we’ll throw you a few million dollars a year. Throw in Ricciardi’s aversion to paying big bucks for 16- and 17-year-old prospects on the international market, and the end result was a bunch of low-upside players coming up through the system that set back the big league team several years. Meanwhile, SkyDome’s honeymoon period evaporated: A group of investors bought the stadium in late 1998 for $85 million, only to have one of the main partners die and another become ill, casting the building into a state of neglect. Built at a cost of $570 million (Canadian), it was sold to Rogers Communications, the Jays’ parent company, for just $25 million in 2004. That year, the Jays won 67 games, posting their worst record in nine seasons.

On the field and off the field, the Jays were a mess.

Mo Money Mo Problems

After averaging just over $50 million in payroll in 2003 and 2004 while Ricciardi attempted to build Moneyball North, Rogers Communications president and CEO Ted Rogers gave the Jays new marching orders: Spend $210 million over the next three years whatever doesn’t get spent one year carries over to the next. The call came too late for Ricciardi to do much for the ’05 season, with the team’s payroll coming in under $46 million and the Jays finishing below .500 for the fourth time in five seasons.

The next offseason, the floodgates opened. Making perhaps the least Moneyballish move possible, Ricciardi chucked a five-year, $47 million deal at closer B.J. Ryan. The lefty closer would appear in just 155 games over that ensuing half-decade, making the question of whether even giving $47 million to an elite, healthy ninth-inning guy is a good idea. In December 2006, the Jays signed center fielder Vernon Wells to a seven-year, $126 million contract extension, handing him the sixth-largest contract in baseball history at the time; when Ricciardi’s replacement unloaded Wells’s contract four years later, it was considered one of the greatest trades baseball had seen in years, regardless of who the Jays got back. In April 2008, Ricciardi gave outfielder Alex Rios a seven-year contract worth just under $70 million; Rios’s performance fell apart so quickly that the Jays placed him on waivers just 16 months later, then let the White Sox claim him with no compensation, just to get rid of that gigantic financial burden. Smaller moves backfired, such as the three-year, $17 million contract the Jays gave Corey Koskie, which resulted in just 97 games played for Toronto before a trade to Milwaukee for someone named Brian Wolfe. Even some of the moves Ricciardi failed to make looked horrible after the fact, headed by a near-miss on Matt Clement, a right-handed starter who became a three-year, $25 million bust for the Red Sox.

It wasn’t all bad. With Halladay developing into an ace, a five-year deal for A.J. Burnett actually working out not too badly, and a blend of homegrown players and imported veterans chipping in, the Jays compiled their best three-year run since the World Series years. Still, the Yankees and Red Sox were better. Efforts over the years to upgrade the team’s young pitching — from trading David Wells for a young lefty named Mike Sirotka only to have Sirotka’s arm give out almost immediately, to Chris Carpenter’s failure to develop into a front-line starter until he’d left for St. Louis — repeatedly fell short. And the spending misfires would hamstring the team’s ability to make further upgrades in later years.

The Anthopoulos Experience

There really is no clever name to describe the 2013 Jays. It’s not Moneyball or Scoutball or anything that dogmatic, with Alex Anthopoulos taking the best practices from his own organization and others, and striving to avoid the mistake of Jays teams past. Fearing the curse of Wells and Rios, he won’t sign a player for more than five years, nor trade for a player with more than five left on his deal. His approach to collecting young talent is pragmatic, targeting the best talent regardless of whether they’re from the international, college, or high school pools. He trusts his scouts to make the best decisions on all those fronts, making one of his first moves as GM the expansion of the amateur scouting ranks, from 28 to 54. He routinely goes over slot for premium talent in the draft. He’ll re-sign some veteran stars (Jose Bautista for five years, $65 million) and trade others (Halladay for Travis D’Arnaud, Kyle Drabek, and Michael Taylor). Any chance he gets, he tacks on club option years to long-term deals, giving the Jays potential bargain seasons for players who retain their effectiveness all the way through. None of these moves are revolutionary in and of themselves. But by adjusting to circumstances and taking calculated risks, he’s made moves that look good on paper anyway.

Unfortunately, the Jays’ record has moved backward since Anthopoulos took over — 85 wins in 2010, 81 in 2011, and a ghastly 73-win season last year. Blame some of it on players Anthopoulos signed to long-term deals. The goal with Ricky Romero and Adam Lind was to lock them up through arbitration years and early free-agency years, then reap the benefits as they developed into top-tier players; instead, they were replacement-level wonders in 2012, Lind’s bat going limp and Romero unable to find the plate even if he had a compass, Garmin’s entire staff of engineers, and an army of cartographers. Injuries took care of the rest. Newly acquired Sergio Santos lasted five innings before shoulder surgery ended his season. In a span of five days in June, three-fifths of the starting rotation went down with injuries: Brandon Morrow strained an oblique, Kyle Drabek hurt his elbow, and rookie Drew Hutchison did the same, the latter two requiring Tommy John surgery that’ll keep them out for much of this season, too. Meanwhile, lineup linchpin Jose Bautista missed several games, dealing a severe blow to the offense even with Edwin Encarnacion doing a reasonable impression of a poor man’s Joey Bats.

Heading into this offseason, Anthopoulos realized he had one of baseball’s best farm systems at his disposal, but also a timetable that might need two, three, four years before the best of those prospects became legitimate big league contributors. He saw something else, too: The AL East had changed. You’d have gone broke many times writing the Yankees off as too old over the past 18 years, given the many thirtysomething stars who continued to perform and usher New York back to the playoffs again and again. But this winter felt different. Derek Jeter’s ankle was acting up, Mark Teixeira wasn’t the player he once was, and who the hell knew when A-Rod might return. Meanwhile, the Red Sox were trying to claw back from a 93-loss season, the Orioles appeared headed for some regression after compiling the best record ever in one-run games, and the Rays, while still young and talented, projected a pullback of their own with a couple more key veterans leaving.

So Anthopoulos did what Ricciardi had tried to do multiple times: He went all-in. Where Ricciardi tried to make moves while his AL East rivals were at their strongest, Anthopoulos waited until the division was as weak as it had been in years, then pounced. And where Ricciardi took half measures, signing Corey Koskies and B.J. Ryans and A.J. Burnetts, Anthopoulos raised the stakes. First came the mega-blockbuster with the Marlins, acquiring Josh Johnson, Jose Reyes, Mark Buehrle, and more in a trade that rocked the baseball world and made clear that Toronto would start acting like the big-market team it is, with Rogers’s blessing. A few days later Anthopoulos signed Melky Cabrera, cheap, to be the team’s new left fielder. Four weeks after that, he polished off his rotation rebuild, landing defending NL Cy Young winner R.A. Dickey. For Jays fans frustrated by the mismanaging of Rogers’s largesse under Ricciardi, then pissed off that Anthopoulos’s Jays had failed to land Yu Darvish and other coveted free agents, these moves signaled the kind of financial commitment that could finally match Anthopoulos’s zeal for deals.

Will it work? Well, not necessarily. Johnson, Reyes, Brandon Morrow, and others have checkered health histories. Buehrle is past his prime and might top out as a league-average pitcher in the AL East, if that. Will the Jays get 150-plus games from Bautista? Will Encarnacion repeat last year’s barrage? Are Lind and Romero salvageable? And when are we going to get that Brett Lawrie breakout, anyway? And while the farm system still has some talent left, there are few prime prospects left to cash in if the Jays need reinforcements at the deadline.

You go for it anyway. You go for it because Toronto finished 25th in starters’ ERA (4.82) and 28th in FIP (4.91), and no aspiring contender can live with that. You go for it because the window’s open, with the Yankees suddenly becoming misers obsessed with the luxury tax, and the rest of the division facing even more questions than the Jays will. You go for it because the Leafs are still the Leafs, the Raptors are still the Raptors, and the city is practically screaming for a winner. You do it because now that the Jays have achieved Internet glory, it’s time for some real-life glory.

You do it because Joe Carter’s been playing golf for a while now, and 20 years is a hell of a long time.