Dream Sports Matchups We Wish We Could See

As we try to escape the nightmare that was the COVID-impacted 2020 sports year, let’s turn instead to dreams of a happier nature. What would be the most incredible sports matchups we could imagine? What athlete or team would we love to see take on another? Sure, we can probably plug in a video game and simulate it, but what fun is that? Well, it actually sounds like a LOT of fun, but I’m 50 years old and have long forgotten how to play cool video games, so let’s just do this instead, ok? Here’s the 5 “DREAM” sports matchups I’d like to see.

Honorable Mention

Of course there are dozens of great hypothetical matchups. There’s the best NFL offense (maybe the 1989 49ers, maybe the 2019 KC Chiefs) against the best NFL defense (the 1985 Chicago Bears).

Maybe the best Duke college basketball team (1992, starring Christian Laettner, Grant Hill and Bobby Hurley) against the best UNC team (1982, featuring James Worthy, Sam Perkins, and some Freshman named Mike Jordan).

Baseball has some incredible potential personal matchups, like watching Peak Pedro Martinez (1999-2000) face the best hitter of all-time (Ted Williams). Or something REALLY interesting, how about watching Rickey Henderson try to steal second base against an Andy Pettitte/Johnny Bench battery, with Javier Baez, the quick-tag artist, covering second?

But those are all prelude. Let’s get to the real thing.

Muhammad Ali (1967) vs Mike Tyson (1988)

The Greatest versus The Baddest Man on the Planet. Tyson was an amazing physical specimen, one of the most powerful punchers in boxing history, and almost certainly the most intimidating heavyweight of all-time. Ali was the most charismatic athlete of the 20th century, and oh yeah, he could box a little. He had amazingly fast hands and feet, was a master of psychological warfare, had a ton of heart and incredible endurance. They say styles make fights, and this would have been a fascinating contrast. You think they could have sold some Pay Per View tickets for this one?

So who wins? Ali wasn’t intimidated by George Foreman and he wouldn’t have been scared off by Iron Mike. Tyson would hope to overwhelm him from the opening bell and score one of his patented early round knockouts, but I say Ali weathers the storm and eventually he wears his opponent down. Tyson is exhausted by the 12th round and Ali finishes him off in the 13th. The Champ is Here!

Martina Navratilova (1984) vs Serena Williams (2002), Wimbledon Finals

The match has to take place at Centre Court (where nobody knows every bounce as well as Martina) for it to be a match. Navratilova won Wimbledon 9 times and was simply the greatest serve-and-volleyer in the history of women’s tennis. Serena has won Wimbledon 7 times and hits harder groundstrokes than any female player ever. Generally speaking, trying to pit a 1980’s tennis player against a modern one is a fool’s errand, as the players hit the ball with SO much more pace today, thanks in part to better technology and training, and the fact that for the most part, bigger and stronger athletes play tennis today than they did in the 1980’s. But Martina was a full generation ahead of her time in terms of physical fitness, and the fact that she served and volleyed, and that NOBODY on the women’s side does it today, would make for an uncomfortable day at the office for Williams.

So who wins? Martina wins the first set, as Serena is slow to adapt to her aggressive, net-charging style, and she makes too many errors as she tries to overwhelm Navratilova with her power. Eventually, however, she finds her groove, and the discrepancy in pace starts to take it’s toll. Serena wins a 2nd set tiebreaker and rolls in the third set. Which is annoying because I was rooting for Martina.

Tiger Woods (2000) vs Jack Nicklaus (1975), Back 9 at the Masters

They say the tournament doesn’t start until the back 9 on Sunday. “They” are wrong on any number of levels, but let’s go with it and assume these two legends are tied as they make the turn and head towards Amen Corner. The argument for who is the greatest golfer of all time contains these two and nobody else, and with good reason. 18 major titles for Nicklaus, 15 for Woods (so far). Jack has 6 Green Jackets, Tiger has 5. Jack’s most iconic win was his 6th and final Masters title at the age of 46 in 1986. Tiger’s was arguably his first Masters win in 1997, when he won by a ridiculous 12 strokes and basically broke the course, forcing the powers that be to lengthen the course so he wouldn’t keep hitting pitching wedges into unprotected greens. Each had the biggest galleries in the sport, and both knew every inch of Augusta National, including every break of every green.

So who wins? Jack made every putt he had to make throughout his career. EVERY ONE. Except of course no, he didn’t, nobody did. But it seemed that way. Of course, you could say the same thing about Tiger at the height of his powers. Jack was probably a bit more consistent (he had 19 second place finishes to go with the 18 wins at Majors), and nobody could think their way around a golf course better than he could. But Tiger at his best was basically Jack 2.0 – way longer, a better ball striker and purer putter than any of his contemporaries, and I don’t think anyone has ever played better golf than Eldrick Woods did in the year 2000. I say Tiger eagles 13 and 15 and wins by a stroke.

1998 Yankees vs 2018 Red Sox

The 1998 New York Yankees are often called the greatest team of the modern baseball era (however you choose to define that). They won 114 games in the regular season and lost only twice in the playoffs en route to the franchise’s 368th World Series title (actually their 24th but whatever). They were not one of New York’s more star-filled teams (currently only two players on the roster, Derek Jeter and Mariano Rivera are in the Hall of Fame) and a starting rotation of Orlando Hernandez, David Wells, David Cone, Andy Pettitte and Hideki Irabu doesn’t exactly remind anyone of the 1970’s Orioles rotations or anything. But they just won and won and won. The 2018 Red Sox were the best Sox team ever (and that’s certainly saying something), and they were far more top-heavy than the ’98 Yankees, being led by super-duper stars Mookie Betts (MVP), JD Martinez (led all of baseball in RBI’s and total bases, and had a ridiculous slash line of .330/.402/.629) and Chris Sale (certainly in the discussion for the best modern pitcher never to have won the Cy Young Award). The Sox blitzed through the regular season, winning a franchise record 108 games, and then navigated the most difficult postseason path ever, beating three 100-win teams (including those pesky Yankees) and only losing three games in the process.

So who wins? It’s impossible to predict how a 7-game baseball series would go, but as a life-long Red Sox fan (and sports pessimist), if forced to guess I would say the shaky relief pitching of Craig Kimbrel would be Boston’s Achilles heel, and of course the great Mariano Rivera would not be New York’s (unless its’s 2004 of course). Yankees in 7.

1986 Celtics vs 1996 Bulls

I grew up watching my favorite athlete, Magic Johnson, and my then-beloved Lakers take on the evil Boston Celtics and Larry Bird. Now I think of myself as a fan of those great Celtics teams, and especially of Bird, but let’s just attribute that to old age and the likely onset of dementia and move on, shall we? Anyway, the best team of that era was the 1986 Celtics, who still had Bird, Kevin McHale, Robert Parrish and Dennis Johnson (mostly) in their primes, and added a rejuvenated Bill Walton, who seemed born to play on that team. They passed the ball like no other team in NBA history, and were more unselfish and smarter than any team I ever saw. They lost only one home game that year and their only disappointment was not getting to beat the Lakers in the Finals (they had to settle for abusing the Houston Rockets). The 1996 Chicago Bulls just absolutely destroyed the league, winning 72 games in the regular season and steamrolling everyone in the playoffs on their way to their 4th title in the Jordan era. Michael Jordan was Michael Jordan, Scottie Pippen had gone from side-kick to NBA super-star, and Dennis Rodman gave them defense, rebounding and toughness.

So who wins? That Celtics team seemed utterly unbeatable, but they would have had no athletic answer for Jordan and Pippen, and while Pippen and Rodman wouldn’t have been able to lock up Bird and McHale (nobody could), they would have slowed them down, and the Bulls overall team defense would have been a nightmare for a Boston team that never had to face defenders as talented as Chicago’s. And as for Jordan, the 1986 version of him scored 63 against those Celtics in the playoffs, and the 1996 version was better. Bulls in 6.