After playing high school baseball in the Bronx, Bobby Bonilla would play briefly at the New York Institute of Technology before being signed by the Pittsburgh Pirates as an undrafted free agent in 1981. In December of 1985, he was drafted by the Chicago White Sox in the Rule 5 Draft, as he was not protected in the Pirates' organization. In April of 1986, he made his MLB debut with the White Sox, but in July of 1986, traded back to the Pirates for pitcher Jose DeLeon. He would play six seasons with the Pirates alongside Barry Bonds. In four of those seasons, he was an All-Star, and in 1990, he finished second only to his teammate Barry Bonds for National League MVP. None of this explains why Bobby Bonilla Day is celebrated on July 1st of every year. In 1999, the Mets traded for Bobby Bonilla from the Los Angeles Dodgers for relief pitcher Mel Rojas to add a veteran right-handed hitter to their lineup. After an atrocious season with the Mets, they decided to release Bonilla, but instead of buying out his contract, which had one year left at $5.9 million, they deferred the payments until 2011 at an 8% annual interest rate. The Mets had investments tied to Bernie Madoff's funds and felt they would put the money there instead and outpace the 8%. The payments to Bonilla would last from 2011 to 2035, and every July 1st, he would be paid $1.19 million. Deferred contracts are a big deal today. The Los Angeles Dodgers have put together an incredible team by deferring payments to superstars like Shohei Ohtani, but Bonilla's agent wasn't the first to come up with the idea. In the 1950s, Ted Williams deferred $50,000. In the 1980s, Darryl Strawberry and Bruce Sutter took deferred payments. Bonilla had a very successful career with a WAR of 30.2 and hitting 287 home runs, but his legacy will always be remembered for his contract negotiations with the New York Mets. Here is a look at some of his best cards to collect in the hobby today. 1998 Metal Universe Precious Metal Gems PMG /50 PSA 7PSAPrecious Metal Gems (PMG) are highly sought after in the hobby and can go for thousands of dollars. In 2024, a Bobby Bonilla PMG card, graded a seven by PSA, sold for $1,680. Bonilla would play for two seasons with the Marlins and help them win the World Series in 1997 with a crucial home run in Game 7. That would be his one championship in his 16-year career. 1999 Metal Universe Precious Metal Gems PMG /50 PSA 8PSAAnother PMG from the following year, with Bonilla in a Dodgers uniform. He played half a season with the Dodgers in 1998. He played for eight teams total in his career. The Pirates were where he had his longest tenure, with six seasons. Topps Desert Shield PSA 10CardladderBonilla's career highlights were playing with the Pirates. Four of his six All-Star selections were with the Pirates, and he finished in the top three in the MVP voting in back-to-back years with the Pirates. 1993 Finest Refractor PSA 10CardladderRefractors are not new to the hobby, and the ones from the 90s, graded a ten by PSA, can be worth a lot. The 1993 Finest Refractor sold for $430 in 2020. 1986 Topps Traded Tiffany PSA 10CardladderBonilla would play part of his rookie season with the White Sox, but his Topps Tiffany rookie card is of him in a White Sox jersey. He would only play 75 games with the White Sox before going back to the Pirates, where he signed as an undrafted free agent. Add us as a preferred source on GoogleFollow