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Breaking Through: Athletes Who Finally Won a Title

Breaking Through: Athletes Who Finally Won a Title


The glory of winning a championship is often the pinnacle of an athlete’s career. It’s the goal every athlete wants to reach and is often the crowning achievement above any other accolade. Some athletes have their fingers nicely adorned with an assortment of rings, while others could never win a championship. And then there are those athletes who shined in their sport but appeared destined to finish their careers just as legends, not as champions.

But then, with all hope to win a championship seemingly extinguished, these fortunate players triumphed to the status of champion, erasing years of doubt and frustration. Following Alex Ovechkin’s intense quest to the 2018 Stanley Cup with the Washington Capitals, let’s take a look back at some of the best athletes who persevered until they could eventually call themselves champions.

1. Alex Ovechkin

The Gr8 one came into the league as one of the most highly-touted players over the last few decades as a Russian skater from Dynamo Moscow.

Taken first overall in the 2004 NHL Draft, Ovechkin’s rookie season was put on hold due to the NHL lockout. After playing in his native Russia for one year during the lockout, Ovechkin made his long-anticipated NHL debut in the 2005 season, the same season that arch-rival Sydney Crosby skated his way into the NHL.

The 2005 season would be the start of Ovechkin’s long-standing rivalry with Crosby, who would go on to win three Stanley Cups, often eliminating Ovechkin’s Capitals in the process, before Ovi finally was able to hoist his first in 2018.

Ovechkin’s notable playoff struggles weren’t exclusively tied to bowing out to the Penguins. On more than one occasion, Ovechkin and his Caps went into the playoffs with the NHL’s best record and were regarded as favorites to capture the Cup. Throughout the course of his amazing career, Ovechkin faltered in the playoffs a staggering eight times, often in depressing, humiliating fashion. Whether it be a Game 7 defeat, a close series against his main rival Crosby, or getting swept out from the playoffs after impressive regular-season finishes, Ovechkin just couldn’t construct a winning playoff formula.

His luck, however, would finally turn in the 2017-18 season, when he and his squad would beat the Vegas Golden Knights in the Finals, ending Vegas’ magical bid for the Cup as an expansion team. After conquering the hockey world, the party really began for the 32-year-old Ovi, and rumor has it he hasn’t been sober since lifting hockey’s most-coveted trophy.

2. John Elway

An iconic quarterback who played his entire career for the Denver Broncos, John Elway’s path to greatness was far from easy, and winning the Super Bowl was even harder for this Hall of Famer.

Drafted first overall out of Stanford in 1983, Elway had an immediate impact on the Broncos, and by his third season in the league, he had the Broncos playing for a championship after leading one of the most famous drives in NFL playoff history. Known as The Drive, Elway’s 98-yard march against the Browns in Cleveland was one of Elway’s early defining moments as he passed for the tying touchdown with 37 seconds left. The Broncos would eventually win the game in overtime, only to be throttled by Phil Simms’s New York Giants in Super Bowl XXI.

Elway would shake off this Super Bowl defeat and lead his team back to the promised land the following season, only to be dismantled by the Washington Redskins by a final score of 42-10. Elway, still young, was seemingly unfazed by back-to-back defeats and would lead the Broncos to yet another Super Bowl two years later. The result would prove to be no different, as the Broncos were absolutely annihilated by Joe Montana and the San Francisco 49ers, 55-10, still the largest margin of defeat in a Super Bowl.

It would take Elway eight full seasons to get back to the Super Bowl, where he and Terrell Davis would break down the barriers that previously blocked Elway’s path into football immortality. Behind the stellar play of Davis, the Broncos emerged victorious in a seven-point victory over the defending champion Green Bay Packers in Super Bowl XXXII. What a sigh of relief.

The following season, Elway would once again reach — and win — the Super Bowl, this time against the Atlanta Falcons. Following a thrilling performance by Elway, he decided that 16 years of memorable victories, injuries, and a handful of agonizing defeats was enough. At the top of the football world, Elway announced his retirement and walked away from the game as one of the most legendary quarterbacks to ever play. His spirit truly was unbreakable.

3. Kevin Garnett

The Big Ticket’s journey towards punching his ticket to the NBA Finals was long, arduous, and at times very frustrating.

By the time KG won his first NBA Finals, his trophy case was about as full as anyone’s in the league. One piece of hardware remained missing, however. Garnett, despite the All-Star appearances, MVP award, Defensive Player of the Year award, and All-NBA first-team selections, would never enter the upper echelon of the game’s greats without becoming a champion.

Originally drafted straight out of high school, Garnett’s impact on his team — the lackluster Minnesota Timberwolves — was immediately felt. In just his second season, the Garnett-led T-Wolves made the playoffs for the first time in franchise history, only to be promptly swept by the Rockets and Hakeem Olajuwon. The following season, Garnett and point guard Stephon Marbury would again lead the T-Wolves to the playoffs, this time bowing out in a close five-game series to Gary Payton’s Seattle SuperSonics.

This disappointment would be just the start of sour things to follow. Garnett would lead the T-Wolves to an impressive eight straight playoff appearances, including a gut-wrenching Western Conference Finals loss to the Los Angeles Lakers in six games.

Garnett’s run with the Timberwolves came to an end in 2007, due to a blockbuster trade that shook up the league and sent Garnett to the Boston Celtics. Here, Garnett would pair up with Paul Pierce and Ray Allen, forming one of the original “Big Threes.”

This trade changed the course of Garnett’s already legendary career. In his first season playing for the Celtics, Garnett and the C’s would storm their way through the regular season and into the Finals. Garnett and the Celtics would dispose of the Lakers in six games, claiming the Celtic’s 17th banner in team history.

Garnett, finally a champion, notably screamed on the court “anything is possible,” and will forever be remembered as a Celtics great following his five-year stint in Boston.

4. Marian Hossa

Heartbreak. That would appropriately describe many, but especially two, of Marian Hossa’s 19 NHL seasons.

As a member of the Ottawa Senators, Hossa led his team to six playoff appearances, losing every time. Ottawa, needing to change the direction of their franchise, decided in 2005 to ship Hossa down south to the Atlanta Thrashers, a perennial loser. As a member of the now defunct Thrashers, Hossa and his scoring abilities would turn the fate of the franchise around and lead them to their first playoff appearance in franchise history. Yet once again for Hossa, the playoffs would end without a championship.

Following another playoff disappointment, Hossa would again change teams, signing with the Pittsburgh Penguins in 2008 at the NHL trade deadline. Joining an already impressive lineup with stars such as Crosby and Malkin, the Penguins seemed destined to lift the Cup.

After skating through the Eastern Conference, Pittsburgh would meet a formidable foe, the Detroit Red Wings. In an intense series that would go six games, the three-headed scoring trio of Malkin, Crosby, and Hossa would fall just short of defeating a Red Wings team full of future Hall of Famers.

After that stinging six game defeat, Hossa pulled a surprising move and signed with the team that just defeated him, spurning the Penguins’ lucrative contract offer.

Hossa signed a one-year contract in a move clearly designed to get him his first ring.  Well, ring-less Hossa would remain.

As a matter of fate, Hossa and the Red Wings would make it to the finals in back-to-back appearances against, you guessed it, the Pittsburgh Penguins. This time the script would be flipped, and in another nail biting series that went seven games, Crosby would come out on top to hoist the first Cup of his career.

As people say, good things (or bad) come in threes. Marian Hossa proved this axiom to be true. After yet another heartbreak in the Finals, Hossa went and changed teams for the third time in three seasons, this time suiting up for the Chicago Blackhawks in 2009.

As a Blackhawk, Hossa would go to his third consecutive finals, with his third different team. Hossa, this time, would finally crack the curse that had kept from being a champion. After a strange six-game series, Patrick Kane would hit the game-winning goal in overtime that gave Chicago, and Hossa, the Cup. Hossa’s move to Chicago panned out exceedingly well for him, and after capturing his first title, he would win two more over the course of the next five seasons.

5. Ray Bourque

After 20 Cup-less seasons playing for the Boston Bruins, time was running out on legendary Ray Bourque in 2000. He was arguably the league’s most iconic defenseman. He collected every trophy seemingly possible — except for one. Bourque was an NHL living legend. But for Bourque, one of the league’s most prolific scoring defenseman in history, winning the Stanley Cup seemed all but impossible. It looked like an almost inevitable conclusion that this skater would hang them up — after two decades in the league — without winning a title.

During the 1999-00 season, the Boston Bruins began to spiral out of control. Making the playoffs was out of reach and Bourque’s patience was wearing thin. Before the deadline, Bourque requested a trade to a contending team in a last-ditch effort to win.

His career with Boston would finish after 20 years and his career with the Colorado Avalanche would begin with a blank canvas. In his first half-season with the Avalanche, Bourque’s impact on and off the ice was immediately felt, but disappointment would rear its ugly head once more as the Avs would lose in the Western Conference Finals to the Dallas Stars.

Now, Bourque’s gas tank was officially running near empty. The light was on. He had one final season left in his legs. For Bourque, it really was do or die, and for the Avalanche there was no greater time than now to win the Stanley Cup. After an impressive regular season, the Avs would make it all the way to the Cup Finals, where they squared up against the New Jersey Devils.

Despite all odds and finding themselves trailing the series going into a potentially decisive Game 6 in New Jersey, the Avs staved off elimination and brought the series back to Denver, where Bourque would finally lift Lord Stanley’s cup after a thrilling Game 7 victory.

That memorable Game 7 would be the last game of Bourque’s career. In a kind gesture to the Bruins fans who rooted for him for 20 years, Bourque brought the cup to Boston’s city plaza to celebrate his success and recognize the greatness he achieved in Boston. It was a fitting end for a player who looked destined to miss out on glory after years of defeat and close calls.

6. Pedro Martinez

One of the Boston Red Sox’s most notable pitchers in their illustrious history, Pedro Martinez was no stranger to the spotlight. The spotlight for Pedro wasn’t necessarily restricted to throwing gems on the mound. Pedro could often be found at the center of a baseball fight throwing punches. Batters it seemed, weren’t too fond of this high-heat throwing, cocky right-hander from Dominican Republic.

Originally drafted by the Los Angeles Dodgers in 1988, Martinez’s MLB debut came in 1992, one of only two seasons Martinez would end up playing for the Dodgers. Although Martinez proved to be effective as a relief pitcher, he was utilized in a trade that sent him to the Montreal Expos. Here, Martinez’s career really took off and he became known as one of baseball’s most dominant pitchers. Despite his small stature, Martinez threw with huge velocity and exercised master command over his pitches. As an Expo, he would win the franchise’s only Cy Young Award but would fail to make it to the postseason.

During the fall of 1998, Pedro was traded from the Expos to the Boston Red Sox. Martinez became a fan favorite in Boston and continued to dominate baseball from the mound. But his success didn’t initially didn’t translate into World Series victories.

During his first two seasons in Boston, the Red Sox made it as far as the 1999 American League Championship Series, but were bounced out by the eventual champions and bitter rival, the New York Yankees. From that season until 2002, Pedro and the Red Sox failed to reach the postseason. In 2003 the Red Sox suffered one of the most catastrophic baseball collapses in recent memory. In Game 7 of a thrilling series against the Yankees, Red Sox manager Grady Little made the incredibly controversial call to keep a wilting Pedro in the game for the eighth inning with the Red Sox clinging to a three-run lead.

But the lead would disappear and the game went to extra innings, where the Yankees would win 6-5 in 11 innings on Aaron Boone’s solo shot. The move to keep Martinez in the game baffled fans and spectators around the world and cost the Red Sox the game and chance to play in the World Series.

Following that epic collapse, Little was fired and the Red Sox hired Terry Francona. This move turned out to be an incredible turn of fate for the crestfallen franchise. The Red Sox would come back from a 3-0  series deficit against the Yankees in the 2004 ALCS and win their first World Series in 86 years by sweeping the St. Louis Cardinals.

Pedro, who threw a gem in Game 3 in St. Louis, would win, in his 13th season, his only ring of his career. Although he never won again, he is fondly remembered in Boston for his critical role in breaking the Curse of the Bambino.

7. Dan Jansen

The Olympics come around every four years. Countless hours of training, blood, sweat, and tears go into making the Olympic team. For American speed skater Dan Jansen, the Olympics proved to be very unforgiving, at least the first three that he participated in.

In 1984, at just 19, Jansen participated in his first Olympic Games in Sarajevo. Although he did not medal, he produced a good showing and came in fourth in the 500m.

Four years later at the 1988 Calgary Olympics, Jansen, coming off a World Cup championship in 500m and 1000m, had a shot at redemption and was considered a favorite to capture gold. However, tragedy struck Jansen at the most inopportune of times.

Hours before his race, Jansen spoke to his dying sister for the final time. As Jansen stepped to the starting line, his sister having just passed away from her battle with cancer, something wasn’t right. During his 500-meter race, he slipped and tragically crashed his way out of medal contention. During the 1000m, four days later, Jansen fell again.

Getty Images/ Mike Powell

1992. Albertville, France. Jansen’s third Olympics. Jansen again proved to be an excellent skater on the world circuit and arrived at the Olympics as one of the favorites to medal. Again, the podium would remain elusive. Jansen, not falling this Olympics, missed out in the 500m by .20 seconds and placed 26th in the 1000m. Gutting. He was .20 seconds away from putting his demons behind him.

As many of you are thinking, weren’t the 1996 Olympics held in Atlanta a Summer Olympics? Where was the Winter Olympics? Well, the Olympic committee had earlier decided to change up the Olympic schedule and have alternating Olympics. Thus, two years after the 1992 Games in Albertville, the 1994 Winter Olympics were held.

Jansen would go to Lillehammer, Norway, again as a potential favorite after having yet another successful World Cup tour. During the 500m, Jansen once again failed to medal, finishing his event in eighth place.

Now it all came down to the 1000m, realistically his final shot at capturing Olympic glory. And what happens? Jansen has the best race of his Olympic career, and in his fourth and final games, captures the gold in the 1000m in record setting fashion.

8. Charles Woodson

Quarterbacks were warned: passing to Charles Woodson’s side of the field was a death trap. With his impressive athletic ability and field awareness, Woodson was a cornerback-safety combo who could change the game at any moment. He is currently tied at first for most defensive touchdowns in NFL history at 13 and is fifth all-time for career interceptions.

Woodson could control receivers and dictate the game’s flow from a defensive standpoint. What Woodson couldn’t control was his lack of playoff success. Prior to winning the Super Bowl, Woodson fell short in five different playoff appearances playing for both the Oakland Raiders and the Green Bay Packers.

The most notable loss would come at the hands of the virtually unknown Tom Brady in a frigid game at Foxboro Stadium in 2002. Woodson, coming off a corner blitz late in regulation, appeared to have strip-sacked Brady in a momentous play that most likely would have sent Oakland to the AFC Championship game. The call was overturned and ruled an incomplete pass in what is today known as the infamous Tuck Rule, and, as you all know, the rest is history. Oakland would lose the game by three points in overtime and New England would launch a dynasty that few sports teams in history could match.

The following season wasn’t much sweeter either. Woodson and the Raiders would make it to the Super Bowl, only to get demolished by Tampa Bay.

Another deflating loss Woodson had to deal with was the legendary 2007 NFC Championship game played in Green Bay. Woodson’s Packers entered the game as favorites against a New York Giants team who, in all reality, shouldn’t have been at the game. But they were, and they took their lucky streak all the way to the Super Bowl, where they upset the heavily-favored, undefeated New England Patriots.

Before that epic upset, the Giants also upset the Packers. At Lambeau Field. In sub-zero temperatures. This was a Packers team many thought had the best chance to go to the Super Bowl and defeat New England. But a myriad of strange calls, bounces, and unlucky plays and it was Woodson and the Packers packing up their bags as their season concluded.

Three years after that freezing defeat, at the ripe age of 34, Woodson would finally hoist the Lombardi trophy — albeit with one arm after breaking his collarbone in the first half.

9. Wade Boggs

Twelve-time All-Star. Eight-time Silver Slugger. Two Gold Gloves, 3,000 hits. And his number retired by three different teams. Wade Boggs left his mark on the game of baseball. Wade Boggs also needed eight postseasons to finally win a World Series.

Boggs entered the league in 1982 and provided the Red Sox with a quality third basemen who could reliably get on base. The 1983 season was when Boggs really marked his arrival to the league as one of the most capable hitters and fielders. In just his second season, Boggs would win the AL batting title and Silver Slugger Award.

When 1986 came around, Boggs was established as one of the league’s most dominant hitters, and the Red Sox were poised to reach baseball’s pinnacle for the first time since 1918. Enter Bill Buckner. Quite possibly the most hated man in Boston sports (ok, Eli Manning, Ray Allen, David Tyree may have since supplanted him), Buckner is best known for letting a routine ground ball squeak through his legs as the Mets rallied to force Game 7. After that crushing defeat, the Mets looked destined to win the World Series, which they did.

Exactly 10 years following this heartbreaking World Series collapse, Boggs was playing for the Red Sox’s arch-rival New York Yankees in the World Series. As a Yankee, Boggs continued his stellar offensive prowess and vastly improved his defensive ability en route to the Yankees six-game victory over the Atlanta Braves. Boggs, despite claiming to be afraid of horses, promptly jumped on the back of a NYPD horse and strolled around the field for a victory lap that kick started the celebration.

10. Gary Payton

The Glove. The best defensive point guard to play the game, Payton had an unreal 17-year career and appeared in the playoffs 13 times before winning a title on his 14th attempt.

Drafted by the Seattle SuperSonics out of Oregon State, Payton played in the Pacific Northwest for 13 seasons. In 1996, Payton and high-flying dunker Shawn Kemp met up with Michael Jordan’s Chicago Bulls in the NBA Finals. The Sonics put up a valiant effort but proved to be no match for Jordan and friends, as the Bulls disposed of Seattle in six games.

Despite being a fan favorite, Payton’s time in Seattle came to a close in the middle of the 2002-03 season, as he was traded to the Milwaukee Bucks. Payton performed well in the half-season he played for the Bucks before signing with the LA Lakers in the offseason.

This signing created a super team as Payton joined the likes of Karl Malone, Shaquille O’Neal, and Kobe Bryant. The Lakers, with their All-NBA like team, failed at winning the championship after losing to the Detroit Pistons in the 2004 Finals. Kind of like a Globo Gym-Average Joe’s style upset. But real. This loss would be Payton’s second Finals defeat of his career and was the final game for legend Karl Malone, who never did win a ring.

Payton would depart L.A. and move to Boston for one uneventful year.  Payton, still searching for a championship to add to his legacy, would sign another one-year deal with his third team in as many seasons: the Miami Heat. He would team up in South Beach with old friend Shaquille O’Neal and emerging superstar Dwyane Wade.

In the 2006 NBA Finals, an aging Payton proved his worth by hitting a few clutch shots throughout the series, including the game winner in Game 3. The Heat would end up winning the championship in six games over the Dallas Mavericks, providing Payton with the only title of his career.

11. Carlos Beltran

Carlos Beltran has durability on his side. He didn’t, for the longest time, have luck on it. Beltran entered the league in 1998 at age 21 and retired in 2017 at the age of 40 after 20 years of solid production in the Majors. Of his 20 seasons, Beltran made it to the postseason on seven separate occasions, faltering in the NLCS three times and the World Series one time before reaching baseball’s highest peak.

Before reaching the pantheon of baseball greats, Beltran had to endure baseball’s notoriously long 162 game season 20 times. Throughout these 20 seasons, Beltran amassed an impressive collection of hardware that includes the AL Rookie of the Year Award, three Gold Gloves, two Silver Sluggers, and nine All-Star appearances.

He was also the victim of a 2013 World Series loss to the Boston Red Sox and, in 2006, was the final out in the NLCS matchup between Beltran’s Mets and the St. Louis Cardinals. Beltran, a feared hitter, struck out looking on a hellacious 0-2 curve by Adam Wainwright. Not a good way to end the season.

Redemption would come for Beltran, however, during his final season. After rejoining the Astros for the 2017 season, Beltran would see some of his power and hitting numbers decline while still playing a crucial role — specifically as a clubhouse leader — for the eventual champion Astros, who beat the LA Dodgers in seven games. Tears of joy were shed for the 40-year-old Beltran who, after years of disappointment, finally accomplished what he set out do when he joined the league 19 years ago.

12. Paul Pierce

The Truth. Celtics legend Paul Pierce will forever be revered by the Boston faithful. Drafted out of Kansas, Paul Pierce took the Celtics by storm.

After surviving a stabbing attack in Boston early in his career, Pierce remained loyal to the city that drafted him and played lights out basketball for the Green for 15 seasons, but calling himself an NBA champion wasn’t so easy.

Pierce constantly had to deal with changing lineups and under-performing rosters. Much to his credit, he stayed patient and believed in the front office (trust the process!). Eventually, Pierce’s patience paid off and the Celtics won the lottery in the massive blockbuster summer of 2007.

They Celtics didn’t get the first pick, but they parlayed their selection in trades that landed them perennial All-Stars Kevin Garnett and Ray Allen, establishing Boston’s Big Three. This unit, in Pierce’s 10th season, would go on to dominate the regular season before facing the Lakers in the NBA Finals. Six games later, the Larry O’Brien trophy was back in a familiar spot: Boston.

Pierce would stay in Boston for another five seasons, albeit without the success he and the Big Three found during that magical 2008 NBA Finals run. Following his departure from Boston, Pierce made stops in Brooklyn, Washington, and Los Angeles (Clippers) before hanging up his signature Nike shoes. Pierce, however, remained true to the franchise that drafted him and retired a Celtic. During the 2017-18 season, Boston held a special night for Pierce when they retired his signature No. 34. Paul’s presence will forever loom over the parquet floor with the other Celtic greats who helped build one of the NBA’s most iconic franchises.

13. Dominik Hasek

The Dominator. Dominik Hasek was pure gold in net. Seriously, he won a Gold medal as the starting goalie for his native Czech Republic during the 1998 Winter Olympics in what was just one of his many notable achievements. For reference, The Dom is one of only seven goalies to win the NHL MVP award (the Hart Memorial Trophy), and the only goalie to win it twice.

Considered one of the greatest and most-flexible goalies of all-time, Hasek rose to prominence while playing for the Buffalo Sabres. As the Buffalo netminder, Hasek guided the Sabres to eight consecutive playoff appearances, each time falling short of the Stanley Cup. Following yet another season of disappointment in upstate New York, Hasek subliminally voiced his displeasure with losing and asked to be traded to a contender.

Access granted. Hasek wound up on a powerful Detroit Red Wings team in 2002 loaded with future Hall of Famers that was favored to win the Stanley Cup. In his first season playing for Hockey Town, Hasek did not disappoint. En route to winning the title in five games, Hasek helped Detroit secure the NHL’s best regular season record.

Hasek, freshly off his first title win, would win another Cup as a member of the Red Wings and secure a bronze medal at the 2006 Winter Olympics at Turin, Italy.

Few goalies in NHL history have done more than Hasek, and it was only fitting that he would retire an NHL and Olympic champion.

14. Jerome Bettis

Notable for his massive figure, Jerome Bettis, often referred to as The Bus, made frequent stops in the end zone over the course of his 13 year career.

Drafted out of Notre Dame by the Los Angeles Rams, this bruising back deemed himself worthy of the first-round pick the Rams spent on him. In his first two seasons in the league, Bettis was selected for Pro Bowls and was the AP Offensive Rookie of the Year winner.

During the 1995 season, the Bus’s route was relocated as the team moved from L.A. to St. Louis. This move, along with a coaching change, severely limited Bettis’s offensive production.

That disappointing 1995 season would be his last in a Rams uniform. Following the season, Bettis was shipped off to Pittsburgh, the city where he would make his biggest mark. Here in the Steel City, Bettis became one of the NFL’s most-feared running backs, running people over and finding the end zone with ease. Reaching the Super Bowl, however, was much tougher for Bettis than reaching pay dirt.

Bettis and the Steelers, despite talented rosters and a future Hall of Fame quarterback in Ben Roethlisberger, faltered in the playoffs on five separate occasions, losing on three occasions in the AFC championship game, just one stop before the Super Bowl.

During Bettis’ last season, Ben Roethlisberger convinced the aging Bettis to return for one final push towards championship glory. The Super Bowl, coincidentally, was to be played in Bettis’ home town of Detroit.

Bettis’ last ride was a magical one. After finally reaching the Super Bowl, Bettis and the Steelers would not be turned away. In a less than thrilling game, the Steelers beat the Seattle Seahawks by a score of 21-10. After the game, the Bus officially changed its sign to out of service and Jerome rode off into the sunset a champion at last.

15. Michael Strahan

Warning: Patriots fans may want to look away here. Feared pass rusher and defensive menace, Michael Strahan played his entire 15-year career for the Big Blue. As a Giant, Strahan put up star numbers from his defensive end position and was a nightmare for quarterbacks and offensive lines. There was no blocking scheme that Strahan couldn’t solve. No quarterback he couldn’t demolish. But there was the Super Bowl. The elusive game that Strahan couldn’t bully or finesse his way into.

During the 2000 season, Strahan would have his first taste of the Super Bowl as the Giants made it all the way to the big game. The big game, however, played itself out more like a nightmare than a dream. Strahan’s Giants would be defeated by a final score of 34-7 in one of the most lopsided games in Super Bowl history. Following this disappointment, Strahan’s game continued to improve. In 2001, a still ring-less Strahan broke the NFL single season sack record by recording an astounding 22.5 sacks, the final one coming at the expense of legendary quarterback Brett Favre.

After Strahan’s Super Bowl embarrassment, he and the Giants would enter the playoffs two more times, exiting early each time. Then, Strahan’s fate would drastically change. During the 2007 season, Strahan and the stout Giants defense fought their way into the playoffs and had one of the most memorable NFC Championship game victories in recent memory by upsetting Green Bay at Lambeau Field in a frozen affair.

The Giants, fresh of this upset, went into Super Bowl XLII as overwhelming underdogs against the high-powered, undefeated New England Patriots. Spoiler alert. The Giants would torment Tom Brady all game and were the beneficiaries of arguably the luckiest catch in sports history. The end result was a massive upset that crowned Strahan, 36, a Super Bowl champion. That insane victory would be his last, as there really was nothing else for Strahan to tackle.

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