Top 100 Jose Canseco Baseball Cards – 2004 Fleer EX Check Mates /25

In 2004, Fleer EX released an incredibly special card — Check Mates.

The name was a clever play on words, pairing two players together while embracing a money theme inspired by U.S. currency. Each player’s autograph appeared on a faux check that was then embedded into the card, perfectly tying together the “check” and “mates” concepts.

Limited to just 25 copies, this booklet stands out not only for its design but also for an unintentional bit of brilliance: both Rickey Henderson and José Canseco were, at one time or another, the highest-paid players in baseball. That makes the money motif even more fitting.

In 1989, Kirby Puckett inked a three-year, $3 million-per-year deal, only for Rickey to raise the bar with a four-year contract at the same annual rate. The following year, José made history as baseball’s first true $5 million man, signing a five-year, $23.5 million contract that paid him $5.1 million in its final season.

While some might wonder why Fleer didn’t pair Canseco with McGwire — a duo that wouldn’t appear together on a booklet for another decade — there’s still plenty of shared history between José and Rickey. Both suited up for the A’s, Yankees, Blue Jays, and Red Sox, albeit at different times.

In the end, Fleer was truly on the money pairing these two former teammates — and former highest-paid players — for their first-ever booklet card: the 2004 Fleer EX Check Mates.

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