Reggie Jackson's $1,000 check to Rickey Henderson features intriguing backstory

All-Star tickets or a card-game debt? Purpose for check raises plenty of questions

Cover Image for Reggie Jackson's $1,000 check to Rickey Henderson features intriguing backstory
Rickey Henderson wrote "I am the best card player" on the back of the 1991 check from Reggie Jackson. (Credit: Goldin/Getty Images)

Rickey Henderson was involved in the most famous card-playing incident in baseball history.

Rickey Henderson also was involved in the most famous check story in baseball history.

Darren Rovell and Will Stern talk about the $1,000 check Reggie Jackson paid to Rickey Henderson.

On Saturday night, a 1991 check made out to and endorsed by Henderson — with a signature that boasts of the Hall of Fame outfielder's card-playing prowess — will sell at Goldin Auctions, and the bidding is already turning heads.

The check is from Reggie Jackson, which alone is not remarkable. Autographs of Jackson and Henderson aren't that rare or expensive.

Jackson checks aren't rare either. In 2014, Goldin sold 100 Jackson-signed checks for a total of $1,853.

The current bid, as of 3 p.m. ET on Friday, for the Jackson/Henderson check, including buyer's premium? $14,640!

The reason? The story behind the check.

Jackson wrote "All-Star tix" in the memo on the front side of the check. (Credit: Goldin)
Jackson wrote "All-Star tix" in the memo on the front side of the check. (Credit: Goldin)

You see, the $1,000 check made out to Henderson from Jackson features a notation in the memo area that says it was for "All-Star Tix."

Jackson was a television analyst at the time for the A's, while Henderson played for the team.

There are a few things suspect about the assertion Jackson was paying Henderson for All-Star Game tickets.

Henderson was an All-Star Game starter in Toronto in '91, and Jackson was at the game, too, playing in the Old Timers Game the day before.

But why would Henderson have access to tickets that Reggie Jackson of all people wouldn't? Plus, it's 1991, the Loonie is 87 cents and good seats to the All-Star Game are $50 face value. Reggie Jackson needs 20 tickets to the first All-Star Game on Canadian soil?

Well, perhaps the "All-Star Tix" memo was a cover.

Henderson wrote "I am the best card player" on the back of the check. (Credit: Goldin)
Henderson wrote "I am the best card player" on the back of the check. (Credit: Goldin)

The All-Star game took place July 8. Jackson gave Henderson the check July 19, and Henderson cashed it a few days later. At some point, Henderson wrote "I am the best card player" on the back and signed it again.

As physical checks do, Jackson wound up with the item, kept it for 34 years and consigned to Goldin Auctions.

In the auction description, Goldin offers up Reggie's comment about the check: "I could never beat Rickey in a game of cards."

Henderson certainly loved his cards. He was involved in the most infamous card game in MLB history, when he and Bobby Bonilla were caught playing cards in extra innings of Game 6 of the 1999 NLCS against the Braves. The Mets were so enraged, the team paid off Bonilla — who is still reaping the rewards from his contract — to not play for them in 2000.

Henderson is also the subject of the most famous check story in MLB history.

In the early 1980s, the Oakland A's accounting department was doing a line-item check and realized the team had $1 million more than it should have. Knowing Henderson had been given a check for $1 million flat, they asked him if it was he who didn't cash the check.

Sure enough, Henderson said he was proud of his earnings, so he framed the check and hung it on the wall in his house instead of cashing it.

Perhaps the check from Jackson to Henderson will also end up framed up a wall soon as well.

Darren Rovell is the founder of cllct.com and one of the country's leading reporters on the collectibles market. He previously worked for ESPN, CNBC and The Action Network.