Milwaukee Bucks: What if Ray Allen had never been traded?

The legacy of Ray Allen‘s tenure with the Milwaukee Bucks will forever be defined by the shortsighted trade deadline deal that sent him to the Seattle Supersonics during the 2002-03 NBA season.

Despite their middling status in recent memory, there have been moments when you can recall exactly where you were or what you were doing on a certain day when something occurred in the history of the Milwaukee Bucks.

Usually those moments are saved for unlikely game-winning shots, celebrating triumphant playoff series victories and if you’re lucky enough, experiencing your favorite team winning an NBA Championship. While the Bucks have had their fair share of buzzer beating victories recently, the latter examples have remained elusive to say the least, considering the team’s 17-year playoff drought and winning their one and only title in 1971.

Of course, these apply to moments off the court as well, with your favorite team either bringing in or re-signing a marquee free agent and/or making a shocking trade can take you aback for a second or make you involuntarily leap for joy, depending on the situation.

More from Bucks History

• The 3 biggest “What Ifs” in Milwaukee Bucks’ franchise history
• 6 Underrated Milwaukee Bucks of the Giannis Antetokounmpo era
• Ranking Giannis Antetokounmpo’s 10 best Bucks teammates of all time
• How well do you know the Milwaukee Bucks’ top 20 career point leaders?
• Looking at important playoff numbers in Milwaukee Bucks franchise history

There may be no better instance of this for Bucks fans than recollecting where they were when hearing the news that the Bucks had sent star shooting guard Ray Allen to the Seattle Supersonics on a trade deadline day blockbuster during the 2002-03 season.

Trading away an in his prime scoring star, like Allen was at the time of the deal, will inevitably draw the ire and frustration out of a fanbase (Allen was in the midst of his age-27 season).

The return, what ended up as a two-month rental of veteran guard Gary Payton and a young, high flying Desmond Mason, only added to the displeasure of the Bucks’ front office and ownership in making such a short-sighted decision.

As time has gone on since the move, the friction between Allen and then-head coach George Karl has become well covered ground in any examination that’s delved deep into why the Bucks ended up moving on from a future Hall of Famer. Allen maintains to this day that Karl just didn’t care much for him as he told Gary D’Amato of the Milwaukee Journal Sentinel earlier this year:

"“The funny thing is, I never had any confrontation with George,” Allen said. “We never had arguments. It was always, ‘George doesn’t like you.’ I was hearing this from other people. Why? I think he didn’t like the way I was, the type of person I was.“There was a Sports Illustrated article about me that said I wore a suit to games, and Karl said I cared more about being cool than being tough. Ultimately, he just didn’t like me.”"

But make no mistake, the impact of sending Allen to the Pacific Northwest was felt almost immediately as it signaled the end of the “Big 3” era, the Bucks’ most recent high point. Former Bucks majority owner Herb Kohl would later call the trading of Allen his “most unfortunate moment” in his 30-year reign owning the Bucks.

That sentiment, from the team’s owner at the time no less, only opens the door for Bucks fans to wonder what things would have looked like had the team not decided to move Allen back on February 22, 2003. Dreaming up an alternate universe in which the former Connecticut Huskies star extended his stay in his first NBA home longer than he ultimately did can only lead to it being a futile exercise for many reasons.

But the star void Allen left behind undoubtedly changed the trajectory of the franchise as they were unable to fill it until the middle years of this decade. There were obvious attempts at doing so on the Bucks’ end and the player to directly benefit from Allen’s leaving, Michael Redd, picked up the lead scoring mantle in his first full year starting as the team’s 2-guard.

It’s also important to mention that the key holdovers from that era all across the roster (Sam Cassell), coaching staff (George Karl) and front office (general manager Ernie Grunfeld) all departed Milwaukee following the end of the 2002-03 season.

Essentially, had the Bucks made the incredibly sensible move of sticking with their then-27-year-old All-Star scoring guard, a major retooling would have likely been in store in the summer of 2003 due to how much everything had eroded after their trip to the Eastern Conference Finals two seasons prior.

Living in a day and age where superstars who are stuck in flux situations are magnified in terms of what might happen in case their teams decide to blow it up may give us an indication of how precarious such a scenario might have been if things continued to go awry.

Above all else, with Allen in the fold, the Bucks had gotten the hard part down in terms of simply having a star player. Regardless of how any alternate timeline would have played out had he stayed longer, we have this reality to learn from in terms of just how crippling dealing away a player of Allen’s caliber can be if you aren’t properly equipped to move forward without him.