{"id":343698,"date":"2026-07-17T18:28:29","date_gmt":"2026-07-17T18:28:29","guid":{"rendered":"https:\/\/www.newsbeep.com\/us-fl\/343698\/"},"modified":"2026-07-17T18:28:29","modified_gmt":"2026-07-17T18:28:29","slug":"richard-jefferson-just-reopened-the-orlando-magics-biggest-regret","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/us-fl\/343698\/","title":{"rendered":"Richard Jefferson just reopened the Orlando Magic’s biggest regret"},"content":{"rendered":"

Before the Miami Heat scooped up LeBron James and Chris Bosh to join Dwyane Wade, or the Golden State Warriors nabbed Kevin Durant on the open market, the biggest free agent scheme that had the NBA worried about its rules resided in Orlando.<\/p>\n

The Orlando Magic’s gambit that began in the summer of 1999, after the lockout-shortened season, to cut salary cap room and make enough space to chase the three premium free agents entering the market in the summer of 2000 is still the stuff of legend.<\/p>\n

Orlando tanked and cleared cap room long before it was fashionable — and still managed a 41-41 season in the memorable Heart & Hustle season.<\/p>\n

That Orlando got two of those major free agents in Tracy McGrady and Grant Hill, two now-Hall of Famers, was a victory in itself. If not for Hill’s injury issues, that era could have seen the Magic atop a very weakened Eastern Conference.<\/p>\n

Still, much of that story is about who the Magic did not get.<\/p>\n

Yes, Hill’s ankle injury prevented him from ever truly taking the floor alongside McGrady, making for an exciting but empty four years without much playoff success.<\/p>\n

The story of how the Magic were unable to get Tim Duncan<\/a> remains one of the Magic’s biggest regrets.<\/p>\n

There are several stories on why Duncan ultimately decided to stay with the San Antonio Spurs. Richard Jefferson added a new reason to the list on a recent episode of Road Trippin’:<\/p>\n

“Tim Duncan is like my big brother,” Richard Jefferson said on Road Trippin’<\/a>. “I love him to death. I remember asking him and he goes: Doc Rivers literally said we’re going to get it done with or without you. And Tim was like, ‘Excuse me?'”<\/p>\n

No one should ever poke the bear with a great player like Duncan. While Duncan is usually seen as a quiet, stone-faced player, he was intensely competitive. Not the kind of player you want to make angry or challenge in that way.<\/p>\n

Rivers has taken the majority of the blame<\/a> for the Magic not getting Duncan. That is at least how it goes in the retelling. But this is a new one.<\/p>\n

And only adds to the pile of one of the biggest what-ifs in Magic history.<\/p>\n

The Magic’s free agent misfire<\/p>\n

It is still hard to call the summer of 2000 a free agent misfire considering the Orlando Magic signed Grant Hill (in a sign-and-trade deal that cost them Ben Wallace) and Tracy McGrady. Hill was already an All-NBA player and McGrady would quickly become one as he became his own star with Hill injured.<\/p>\n

But the Magic really ran a full-court press in one of the first free agent blitzes in league history. They were ready to bring in all three of Grant Hill, Tim Duncan and Tracy McGrady.<\/p>\n

They supposedly pulled out all the stops, making posters with the three players in Magic uniforms, bringing in Tiger Woods to join them<\/a> on the golf course at Isleworth and setting themselves up for a free agency bonanza.<\/p>\n

The original story of how the Orlando Magic lost Duncan was that the San Antonio Spurs simply got the last word.<\/p>\n

Hearing that Tim Duncan was close to picking the Magic, David Robinson cut his Hawaiian vacation short to join Gregg Popovich to go to the Virgin Islands and make one final plea for Duncan to rejoin the Spurs. That appeared to do the trick, and the Magic were left with only two of the three prizes.<\/p>\n

Stories have continued to be told about what happened.<\/p>\n

Grant Hill, along with Bruce Bowen and others, would later claim that the real hang-up came when Tim Duncan asked coach Doc Rivers if family could occasionally travel on the team plane. Rivers, entering his second year as a head coach, said that would not be allowed and that appeared to throw Duncan off.<\/p>\n

Hill also has claimed that the Magic had the wrong kind of food for Duncan’s simple tastes and had to scramble to get cold cuts for their welcome lunch in their recruiting pitch.<\/p>\n

There is at least some belief that the all-out blitz made Duncan uncomfortable and yearn to be where he was familiar in San Antonio.<\/p>\n

Only Duncan and the Spurs truly know what tipped him back in their favor. Only the parties involved know how truly close Duncan was to leaving San Antonio for Orlando.<\/p>\n

Two out of three wasn’t bad?<\/p>\n

The Orlando Magic did not come out complete losers. <\/p>\n

Grant Hill was still the get of the summer after six All-NBA seasons with the Detroit Pistons. And Tracy McGrady built his Hall of Fame career in his four seasons with the Orlando Magic.<\/p>\n

John Gabriel still won the league’s Executive of the Year despite missing on the biggest fish in free agency.<\/p>\n

Still, Tim Duncan not arriving in Orlando that summer was one of the biggest regrets in franchise history. That the Magic have multiple stories of their coach making some misstep in the process — along with other stories of not knowing who they were pitching — leaves a bitter taste.<\/p>\n

Especially considering the Magic never got out of the first round in McGrady’s four years in Orlando.<\/p>\n

McGrady blossomed into a superstar in Orlando, taking the reins and becoming one of the best scorers in the NBA.<\/p>\n

But Hill dealt with injuries for the entirety of his seven years with the team. The Magic had three first-round exits in a row before crashing out with a 21-61 season. McGrady requested a trade at that point. Hill had played only 47 total games in McGrady’s four seasons in Orlando.<\/p>\n

Duncan went on to win four titles with the Spurs after deciding to stay in San Antonio, forming one of the greatest modern dynasties.<\/p>\n

The Magic came out of it all with the number one pick to draft Dwight Howard in 2004. He would lead the Orlando Magic to the NBA Finals in 2009, two years after Hill’s seven-year contract expired and he departed for the Phoenix Suns.<\/p>\n

The whole era is one giant what-if for the franchise. And Duncan’s free agency remains one of the team’s biggest regrets one way or the other.<\/p>\n

\"\"Add us as a preferred source on GoogleFollow<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"Before the Miami Heat scooped up LeBron James and Chris Bosh to join Dwyane Wade, or the Golden…\n","protected":false},"author":2,"featured_media":343699,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[11],"tags":[139,141,140],"class_list":["post-343698","post","type-post","status-publish","format-standard","has-post-thumbnail","category-orlando","tag-orlando","tag-orlando-headlines","tag-orlando-news"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/343698","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/comments?post=343698"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/posts\/343698\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media\/343699"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/media?parent=343698"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/categories?post=343698"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/us-fl\/wp-json\/wp\/v2\/tags?post=343698"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}