25 Best Rickey Henderson Baseball Cards — One for Each Year!

Rickey Henderson baseball cards have been lighting up the hobby almost from the day he first stepped cleat on the Oakland Coliseum dirt and began blazing the base paths.

Even so, in those early days, Rickey was more of a curiosity — a phenomenon, maybe — than a true superstar, as he went about breaking necks and pitcher-catcher spirits with his otherworldly speed and baserunning canny.

It didn’t take too many years, though, for fans and collectors to realize that Henderson was much more than a speed demon.

Here we had a guy who could get on base seemingly at will — via hit, walk, or taking a pitch off his body.

Here we had a guy who could steal any base he wanted, take any risk he wanted on the paths and come out ahead most of the time, and turn even the calmest of opposing managers into a Nervous Nellie Sparky Anderson doppelganger.

And, here we had a guy who developed amazing power for a top-of-the-order batter and someone who was speed-first.

In short, here we had a guy who became the greatest leadoff hitter the game has ever seen, and a top-tier Hall of Famer.

Along the way, Henderson’s cards rose in hobby status right along with the man’s own star, and collectors today relish (!) the sight of cardboard featuring one of the game’s great hot dogs.

And there are plenty of them — Rickey played in the major leagues for 25 years!

Indeed … it would be nearly impossible to detail each of his thousands of individual cards in a space like this one, so we’ll instead focus on the best of the best.

What follows then, are the 25 greatest Rickey Henderson baseball cards of all time, one for each season he played, as chosen by yours truly.

My criteria?

Card value to some small extent, but mostly historical significance in the context of Henderson’s career and the hobby, and, especially, aesthetic appeal.

You won’t agree with some (most? any?) of my choices, but you can’t argue the fact they’re all great.

They are, after all, Rickey Henderson baseball cards.

(Note: The following sections contain affiliate links to eBay and Amazon listings for the cards being discussed. Prices culled from the PSA Auction Prices Realized Tool for the most populous condition of each card, according to the PSA Population Report.)

1980 Topps Rickey Henderson (#482)

Even if Rickey did have another rookie card to compete with this one, I’d lay dollars to bat donuts the 1980 Topps Henderson would take top billing here.

This card just “works” visually, with the card accents perfectly complementing Henderson’s uniform, and with the sunshine and impending game action just daring you to try and stay away from the ballpark.

And, of course, this card’s legend grew right along with Henderson’s own, spiking to new heights every time Rickey pulled off his next amazing feat or toppled the next “unbreakable” record.

Today, this beauty stands as maybe the most important and beloved baseball card of the entire decade, which is saying quite a lot considering how the hobby exploded in the nine years that followed.

Condition: PSA 8

Value: $280-310

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1981 Kellogg’s Rickey Henderson (#33)

So, this is a purely aesthetic play.

See …

Rickey had cards in all three major sets in 1981, including two in the 1981 Fleer set, plus an entry in the 1981 Fleer Star Stickers issue. Any of them could have landed here, and most are probably more “valuable” than this one in most situations.

But all of those cards (save maybe the Star Stickers entry) are pretty drab, and there is plenty of blurry photography involved.

This Kellogg’s card, on the other hand, is bright and shiny and, of course, three-dimensional. And it’s also very evocative of the time, when food issues offered up some much needed and much prized variety to the blossoming card market.

Condition: PSA 8

Value: $25-35

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1982 Topps Rickey Henderson (#610)

This entry gives us our first real cardboard-borne glimpse of Henderson doing what first made him famous — wreaking havoc on the basepaths.

And, though pink may not be the first color you think of when pondering the Oakland A’s or their Man of Steal, the accent works well with Oakland Green, and the card pops with electricity overall.

Like other cards on this list, this Rickey is one of the most important in the set it inhabits, and it’s a collector favorite.

Condition: PSA 9

Value: $65-75

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1983 Topps Rickey Henderson (#180)

Yes, there are plenty of Topps cards on this list, but when you’re the best, you’re the best. Or in the vernacular, when you’re The Real One, you’re the real one (and the best).

And it’s pretty much impossible to leave this sunny, action-packed Henderson card off any list of great Rickey memorabilia, especially when you consider there’s a decent chance this shot captures the moment just after the man with the sneaky power teed off on one of his record 81 leadoff home runs.

A stone-cold hobby classic.

Condition: PSA 9

Value: $50-70

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1984 Topps Rickey Henderson (#230)

Sometimes, you blast your way to success.

Sometimes, you streak, driven by blinding speed and brute power, toward your goal.

And, sometimes, when the situation calls for it, you tiptoe up on your prey.

Here on this 1984 Topps card, we get a peek at Rickey in apparent stealth mode, skulking toward another stolen base, or at least toward another hunk of pitcher disruption.

It’s an unusual shot that makes the card one of Rickey’s — and 1984’s — best.

Condition: PSA 9

Value: $20-30

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1985 Fleer Rickey Henderson (#425)

You want to know what long-distance intimidation looks like from the catcher’s point of view?

Well, then, you probably won’t ever find a more perfect embodiment of what must be a mostly helpless feeling than the 1985 Fleer Rickey Henderson unleashed on the hobby.

Here you have Rickey, dead-centered in the frame, crouched and ready to run, eyes searching the pitcher for any sign of weakness. It was doom personified if you were the guy behind the plate.

Fleer topped it all off with an underrated design featuring classy gray borders and a fetching team-colored inner border that made the whole thing pop. As an added bonus, this would be Rickey’s last base Fleer card as a member of the A’s for awhile.

Condition: PSA 9

Value: $35-40

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1986 Fleer All-Stars Rickey Henderson (#7)

This is not the most beautiful Rickey Henderson card ever issued, and it’s not the most action-packed, either.

Heck, the photo is at best a stop-where-you-are practice-field candid, and at worst, a posed moment.

But this just might be the flashiest Henderson card, or at least certainly right up there among his 1986 entries.

It’s also one of the first to show Rickey as a member of the New York Yankees, and it also has a built-in scarcity factor — the 12-card All-Stars inserts were included only in wax and cello packs, and then only “randomly” so.

Heck, it even exists in a “Ricky” error version … talk about 80s-appropriate!

As of this writing, in late April 2022, only about 50 of the two Henderson varieties (combined) have been graded by PSA, leaving it decidedly on the low side, supply-wise, of Junk Wax consideration.

Condition: PSA 9

Value: $15-20

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1987 Topps Rickey Henderson (#735)

Rickey, in pinstripes, in the sunshine, in front of a crowd, with the classic Yankees top-hat logo, all wrapped in wood borders?

Yeah, this card is elecric, iconic, fantastic, and any other “ic” adjective you want to throw at it.

The other 87s can’t hold a candle.

Condition: PSA 10

Value: $60-70

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1988 Score Rickey Henderson (#13)

By 1988, we were firmly in Junk Wax territory, so any latent big-dollar values have developed through late-discovered errors and variations, or condition scarcities.

None of that really applies to Rickey’s 88 cards, though, so we’re left with pure aesthetics.

From that standpoint, the 1988 Topps design is the winner, and Henderson’s Real One card is not bad.

Also worth a look is Rickey’s entry in the 1988 Fleer set, which has a fairly ridiculous design but a front-on Yankees version of the stealthy Henderson sneak we saw on his 1984 Topps card.

The winner here, though, is the 1988 Score Rickey Henderson, his base card in Score’s very first set.

Sure, Score cards didn’t have much character in general, but they did give us full-color photos on front and back of the card, as well as some of the innovations that Upper Deck supposedly “introduced” the next year.

Beyond my soap box, though, this Henderson card is quite striking — here we have a closeup of Rickey’s crouched strike zone, with a sunset tailwind that splashes nostalgia off the backside of his Yankees helmet and Pinstripes.

The purple border only adds to the evening shade effect, leaving the card with a statuesque, almost majestic overall feel.

Condition: PSA 10

Value: $20-30

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1989 Topps Traded Rickey Henderson (#48T)

Henderson spent four glorious seasons in the Bronx after the A’s traded him to the Yankees in December of 1984, but with NYY going nowhere fast and Oakland trying to win another division title, the teams unswapped in June 1989 — Henderson back to the A’s, Eric Plunk back to the Yankees (with other dudes filling out both sides).

Rickey fit right in with the Bash Brothers and turned in a superstar second half to help the A’s win the American League West before nabbing ALCS MVP honors for his two home runs, five RBI, eight stolen bases (and zero caught-stealings), eight runs scored, and ridiculous 1.609 OPS in five games against the Toronto Blue Jays.

It was more of the same in the World Series as Oakland swept to victory over the Giants.

Then Henderson set his sights on the all-time marks in front of him … but not before a cardboard homecoming that fall.

Though Rickey appeared with the Yankees on his base ’89 sets, he was back in the Oakland sunshine on this 1989 Topps Traded card, a blazing entry that even features the Athletics elephant on Henderson’s left sleeve. If this card doesn’t warm your hobby cockles, it might be time for you to take up raisin collecting or tuna can art.

Condition: PSA 9

Value: $90-100

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1990 Leaf Rickey Henderson (#160)

Taken as a whole, 1990 baseball cards are more like a hole — a black hole of overproduction, blah (or hideous designs), uninspired photography … yuck.

Against this backdrop, Henderson did show up on several cards that were at least OK — Upper Deck always looked good in those days. His Score photo was pretty good, even bordering on exciting.

But, absent a truly compelling entry elsewhere, we’re crowning the 1990 Leaf Henderson here, by virtue of a classic batting pose, an understated by classy card design, and an issue — 1990 Leaf — that helped propel us into the era of “super premium” baseball cards … for better or for worse.

Condition: PSA 10

Value: $40-50

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1991 Topps Rickey Henderson (#670)

Pretty much the same stuff I said about the 1990 card market applies to the 1991 scene, too, but Topps did sort of step up their game to celebrate the 40th anniversary of their first baseball card issue.

Gone were the gaudy colored borders (that I’ve grown to appreciate), replaced by a simple, uncluttered, Upper Deck-esque design that emphasized improved photography.

And, on some cards, as on this Rickey, we got landscape baseball cards for the first time since 1974. In this particular case, we got the impending all-time stolen base leader sliding head-first into home plate.

The easy winner.

Condition: PSA 10

Value: $40-60

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1992 Upper Deck Rickey Henderson Grand Theft (#782)

Truth be told, baseball cards were getting pretty sophisticated by 1992.

Fleer and Donruss both made dramatic improvemetns to their base brands and, even though those changes may seem dated today, they raised the entire market 30 years ago.

And, really, pretty much everything that came out that year, and in the years that followed, looked pretty good.

All of which is to say that there are like, a ton, of solid Rickey Henderson cards to choose from in this slot, so … take your pick.

As for my pick, I’m going with something slightly out of the ordinary — the Upper Deck “Grand Theft” card that both celebrates Henderson’s 1000th stolen base (nabbed on May 1, 1992) and gives us a shot of Vernon Wells‘ stellar artwork.

That’s Vernon Wells, Sr. — in case you were wondering — whose son turned out to be a pretty darn good ballplayer in his own right.

Condition: PSA 10

Value: $20-30

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1993 Fleer Flair Rickey Henderson (#260)

By 1993, there were more baseball card brands than you could shake a (streetball) stick at, and, if you couldn’t find something to your liking, you just weren’t trying very hard.

Even among the onslaught of cardboard overwelm, though, 1993 Fleer Flair looked different. It was almost all photo, for one, and it was almost all two photos, for two.

For Henderson, that manifests in a dramatic bat follow-through in the foreground, with a pensive, larger-than-life Rickey looming over the scene from the basepaths in the background.

Not a super valuable card, by any means, but still a visual stunner.

Condition: PSA 10

Value: $40-50

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1994 Fleer Ultra Rickey Henderson (#408)

The market didn’t slow down at all in terms of introducing and proliferating more brands in 1994, even as The Strike loomed on the horizon.

One of those many titles was Fleer Flair, and it’s as good a choice here as any, and better than most.

Featuring mostly photo, this one gives us the blazing Henderson speeed in a blazing white A’s uniform against the eternal green of the baseball diamond.

Perfect, or a decent approximation.

Condition: PSA 10

Value: $10-20

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1995 Upper Deck Rickey Henderson (#30)

By the time the first 1995 baseball cards found their way to market, the diamond world was still mired in that dratted player strike.

The hobby was starting to feel the crunch, too, as apathy toward the messy business side of the game trickled over to our cardboard coffers, at least to some degree.

Against that background, the many, many issues being foisted upon collectors found the demand harder than ever to generate, and some sets hardly got any attention at all. There was also a sameness developing among all the excellence — funny how that works, huh?

The 1995 Upper Deck Henderson card was a bit different, though, showing a high-flying Rickey leapfrogging a (maybe?) Tigers catcher — Chad Kreuter, perhaps? — on the way to the plate.

Nothing special from a value standpoint, but still an interesting and worthy visual.

Condition: PSA 10

Value: $5-10

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1996 Fleer Ultra Call to the Hall Rickey Henderson (#4)

Henderson became a free agent after the 1995 season, and he took his still considerable talents to San Diego.

At 37, Rickey wasn’t quite what he had been ten years earlier, but he still played a full season, stole 37 bases, and scored 110 runs to help the Padres win the National League West in 1996.

Like most other big names of the day, Henderson was featured in about a thousand sets that summer, but not all that many of them showed him with the Padres.

This nifty card, one of ten celebrating Fleer’s designated future Hall of Famers, does. Featuring the artwork of J. Forman, these cards were inserted one per hobby or retail box, and Rickey’s card is appropriately regal.

Condition: PSA 10

Value: $5-10

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1997 Topps Rickey Henderson (#96)

Henderson played 148 games with the Padres in 1996 (and 88 in 1997) before a trade sent him to the Angels.

Among those 1996 contests, he appeared six times in Wrigley Field against the Cubs, including two to open the season. Considering that the April weather in Chicago is, uh, not balmy, generally speaking, and that Rickey is wearing short sleeves (and so are the fans behind him) in this shot, you gotta think a four-game set in June 1996 is the more likely matchup here.

Either way, this card represents one of just 19 total games Henderson played at Wrigley (he came back to the National League a couple times before all was said and done), and the old ballpark is showing some of its finest brick-encrusted ambiance.

Condition: PSA 10

Value: $50-55

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1998 Fleer Sports Illustrated Road to Cooperstown Rickey Henderson (#5)

Rickey’s stay with the Angels lasted all of 32 games in 1997, so there aren’t all that many different Halo Henderson cards running around out there.

But Fleer teamed up with Sports Illustrated to produce three SI-branded sets in 1998, the second of those dubbed “Then and Now.”

Released in April, “Then and Now” came six cards per pack, 24 packs per box, with an MSRP of $1.99 per pack. And, seeded one per box, was a special ten-card insert set celebrating players that Fleer/SI thought were headed to the Hall of Fame — “Road to Cooperstown” was the insert set.

At #5 in that run?

Yeah, it was Rickey Henderson … in his Angels uniform.

Like most other cards of the era, these don’t exactly break the bank today, but they still provide a striking look at some all-time greats, 80% of whom actually have made the Hall of Fame cut — Henderson, Ken Griffey Jr., Tony Gwynn, Greg Maddux, Paul Molitor, Mike Piazza, Cal Ripken Jr., and Frank Thomas.

The outsiders? Their names rhyme with “Barry Bonds” and “Roger Clemens.”

Condition: PSA 9

Value: $15-20

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1999 Topps Rickey Henderson (#277)

Given how noisy both of them are, it’s actually pretty surprising that Henderson and the Mets didn’t find each other until 1999.

But, even though Henderson didn’t appear in a Mets uniform until Spring Training that year, Topps had reduced their turnaround time enough by that point to catch him shagging balls in his NYM warm-ups in their base set.

A good, solid card of a baseball legend, focusing on an aspect of his game (defense) that wasn’t his forte and didn’t garner much attention.

Condition: PSA 10

Value: $50-60

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2000 Fleer Tradition Rickey Henderson (#390)

This card may scream “1954 Topps,” but it was Fleer who dusted off the classic design, tweaked it a bit, and usurped it for their own gain in their 2000 Tradition line.

Heck, the 450-card set even features brown card stock (and backs) like Topps issues of the past.

Copycat concerns aside, this was a fun and striking set, and Henderson looks right at home with the classic intertwined NY on his cap against a bright yellow background.

Condition: PSA 10

Value: $50-60

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2001 Donruss Rickey Henderson (#21)

Henderson only lasted through part of May with the 2000 Mets before they released him.

The Mariners signed him six days later, though, and he stayed in Seattle the rest of the season.

But Rickey became a free agent again at the end of the season, and he lingered on the shelf until the Padres brought him back to San Diego in March.

Later that spring, this 2001 Donruss card captured most of that journey, doing it with typical old-school Donruss flair — dark borders accented with stars, a hinky font or two, art deco shapes (including around the Donruss logo).

It’s also one of the last Big D issues to show team names and logos before their MLB license evaporated.

All in all, a nice-looking, if loud card that fits Henderson well.

Condition: PSA 10

Value: $5-10

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2002 Donruss Originals Rickey Henderson (#379)

Henderson appeared in a Yankees uniform in the original 1988 Donruss set.

Fast forward 14 years, and he had made his way all the way back around to the American League East, this time with the archrival Boston Red Sox (he also dropped in on the East long enough to win a World Series with the 1993 Blue Jays).

At the same time, Donruss was experimenting with the retro game, rolling out several of their 1980s designs as part of a 425-card “Originals” issue. Henderson had cards all up and down the lineup, and in insert sets, but this one gives us a striking look at the late-career speedster swinging in BoSox home whites … in that 1988 Donruss design.

And, while there are enough original (not “Originals”) 1988 Donruss roaming around out there in the wild today for every tree on earth to own one (or a few thousand) of its own, there’s something nostalgic about this Rickey … and it just dares you not to think of the Ellis Burks rookie card.

Condition: PSA 10

Value: $20-40

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2003 Topps Traded Rickey Henderson (#T73)

Henderson became a free agent after the 2002 season, and, when no team came calling by Opening Day of 2003, it looked as if the Kryptonite of time had finally caught up to our Man of Steal.

But no!

The Dodgers signed Rickey in July 2003, and Henderson made it in to 30 games through September 19. In that contest against the San Francisco Giants, Henderson would come on as a pinch hitter in the seventh inning … and was promptly plunked by Jason Christiansen. Rickey advanced to second on a sacrifice bunt from Dave Roberts (yes, him) and then scored on a Shawn Green single with two outs (after Paul Lo Duca had grounded out).

Paul Quantrill came in to pitch the eighth for the Dodgers, replacing Henderson in the lineup.

And … that was it for Rickey Henderson on a big league diamond.

A couple months later, Topps captured Rickey in blue, and wrapped heavily in more blue, in their 2003 Traded issue. It’s a great looking card that took on even more significance when Henderson finally announced his retirement in December … of 2005.

Condition: PSA 8

Value: $15-20

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2004 Upper Deck Rickey Henderson (#188)

Henderson’s continued dalliance with a return in 2004 — or later — introduced enough uncertainty that he landed on some cards in 2004, the year after his last game.

This Upper Deck entry shows Rickey once again using his baserunning skills to taunt some poor pitcher and catcher combo, and the back gives us his full career stats.

This may not be a super valuable card, but it’s hard to sneeze at an action-packed career-capper of a top-tier all-time great.

Condition: PSA 10

Value: $25-50

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