Opinion: Why the Bucks Should Trade for Jrue Holiday

Editor’s note: Today we have a special guest, as longtime basketball fan/ranking Bucks Twitter member/Milwaukee journalist and editor Dan Shafer stops by to do what all NBA fans do best: pitch trade ideas.

I’ll say this: I’m not sure I’m sold on the trade, but Dan makes a strong case for at least considering it. If you like what he has to say, you can (should!) follow Dan on Twitter and check out his site The Recombobulation Area.

The Milwaukee Bucks are 24-4, tied for the best record in the NBA. They have the league’s best net rating and point differential. They have the league’s best defense and second-best offense. They just ripped off 18 straight wins, one of the best winning streaks in NBA history.

So why would now be the time for Jon Horst and the Bucks front office to make a major deal.

The most obvious (and yes, cliché) answer is that championships aren’t won in December, they’re won in June. And as trade season begins, so does the arms race, and teams will be gunning to out-maneuver the best-in-the-league Bucks. Contenders across the league could look very different in the spring, contenders Milwaukee will need to defeat to win a title.

Looking ahead to the spring, it’s not difficult to identify the Bucks’ biggest potential weakness: Playoff Eric Bledsoe.

You’re all Bucks fans, so I apologize for rehashing old wounds, but Bledsoe’s play against Toronto was arguably the biggest reason Milwaukee missed out on its first trip to the NBA Finals in more than 40 years.

In six games against the Raptors, Bledsoe shot just 29.4 percent from the floor, including 17 percent on threes, which completely changed how Toronto was able to defend the Bucks as the Eastern Conference Finals went on. And it’s not like he picked things up in other aspects of his game as his shooting slumped -- his rebounds, assists and steals were all down from his season averages, and his All-Defensive First Team defense simply wasn’t there, as Kyle Lowry and Fred VanVleet torched the Bucks from the point guard position.

It wasn’t just in one series against Toronto, of course. A year earlier, he was outplayed by Terry Rozier en route to the Bucks’ seven-game loss against the Boston Celtics. Could Bledsoe reverse the trend in the 2020 playoffs and produce more like the player he’s been in the regular season? Absolutely. It would be incredible to see that redemption story unfold. But are you confident in that happening? Are you really?

Count me among the skeptics. But scanning through the league, there was no obvious available upgrade at the point guard position that would move the needle enough for the Bucks to cash in some assets and make a deal. Chris Paul? His contract is too much of a burden to move in any realistic trade. DeAngelo Russell? Same, and that’d be a downgrade. Goran Dragic? Jeff Teague? No and no.

But that dynamic just changed. Marc Stein of the New York Times reported that New Orleans Pelicans guard Jrue Holiday is “available via trade.”

Holiday would be a real game-changer for the Bucks, and a clear upgrade over Bledsoe. Turning Bledsoe into Holiday would be a similar -- but bigger -- move than the Raptors turning Jonas Valanciunas into Marc Gasol.

The 29-year-old (yes, younger than Bledsoe) Holiday is one of the more underrated players in the NBA. He’s been an All-Defensive First Team (2018) and Second Team (2019) player, so there’d be no qualms about any defensive downgrade. In fact, Holiday would probably be an upgrade, given how well he played against Damian Lillard and C.J. McCollum in a 4-0 sweep against the Blazers in the 2018 playoffs (a series in which Holiday averaged 27.8 ppg on 57% shooting). Holiday is a better playmaker than Bledsoe, and a marginally better shooter (on a Pelicans team that’s long had cramped spacing). Holiday can play both on and off the ball, and has toggled between starting at point guard and shooting guard in recent years, depending on backcourt personnel in New Orleans. He’d be an ideal backcourt fit next to a more ball-dominant frontcourt playmaker like Giannis Antetokounmpo. He’d arguably walk in the door as the Bucks’ second-best player.

So what could a deal look like?

Obviously, you’d have to start with Bledsoe. Then, you’d have to consider adding the assets acquired in the controversial deal that sent Malcolm Brogdon to the Indiana Pacers. The Brogdon factor certainly plays into this larger conversation. Acquiring those picks -- and having the cap flexibility to re-sign George Hill -- was the tradeoff in letting the potential All-Star guard go to a division rival, and it would be a shame if the Bucks sat idly by without using the one first and two second round picks to upgrade the roster with an NBA championship and a Giannis supermax extension in the franchise’s sights. In addition to providing an upgrade over Bledsoe, a Holiday deal could be a way to alleviate many of the (justified!) concerns fans have over letting Brogdon go.

Jrue Holiday is in the third year of a five-year, $128 million contract, which includes a player option of about $26 million for the 2021-2022 season. Bledsoe is in the first year of a four-year, $70 million deal, which includes a $3.9 million buyout option in the 2022-2023 season.

There’s obviously some distance between those two annual salaries. Most Bucks fans familiar with the trade machine would want to plug Ersan Ilyasova and his $7 million salary into this (or any) trade, given that his deal essentially amounts to an expiring contract. But considering New Orleans’ priorities as a young team that would be looking to build around top draft pick Zion Williamson and 22-year-old breakout forward Brandon Ingram, longer-term pieces might be more valuable than the cap space Ilyasova’s deal would provide next summer.

So here’s what a potential offer could look like:

Milwaukee receives: Jrue Holiday

New Orleans receives: Eric Bledsoe, Sterling Brown, DJ Wilson, Dragan Bender, Indiana Pacers 2020 1st Round pick, Indiana Pacers 2021 2nd Round pick, Indiana Pacers 2025 2nd Round pick

This would give the Bucks a closing lineup of: George Hill, Jrue Holiday, Khris Middleton, Giannis Antetokounmpo and Brook Lopez. That is a team that can win the Finals.

The Bucks would also lose Wilson and Brown, two legitimate rotation pieces, but ones that don’t always see the court on Milwaukee’s ultra-deep roster. The Bucks would still keep Donte DiVincenzo as a key piece and potential starter in the backcourt (it would be tough to give up both DiVincenzo and the Pacers picks in the deal). Wesley Matthews, Kyle Korver and Pat Connaughton would be available on the wing. Ilyasova and Robin Lopez are solid veteran backup bigs. That’s a really good 11-man rotation, even without Wilson and Brown (or Connaughton, if New Orleans would prefer him to Brown).

The Pelicans would then build around Williamson, Ingram, Bledsoe, Redick, their inevitable high lottery pick, the Indiana picks, the remaining haul of picks and swaps from the Anthony Davis trade, a ton of cap space, and a group of under-25 players that would include Jaxson Hayes, Lonzo Ball, Sterling Brown, DJ Wilson, Josh Hart and Nickeil Alexander-Walker. That’s a really, really compelling long-term core.

Is it possible New Orleans could receive a better offer for Holiday? Of course. It’s hard to know how Bledsoe would work there long-term, and GM David Griffin wouldn’t be acquiring any potential lottery picks, key to any deal of this nature. But is another offer that would deliver such assets out there? Zach Lowe suggested a Gary Harris-Michael Porter Jr. package from the Nuggets, but Adrian Wojnarowski characterized Porter Jr. as untouchable for Denver. The Miami Heat could be an option, but is a deal highlighted by rookie Tyler Herro (along with some ugly contracts and no first rounders) a better package than what Milwaukee could offer? Who else, realistically, is there? Most teams are already committed long-term to a point guard. Does Dallas have enough assets after giving up multiple first round draft picks to trade for Porzingis? How much do teams like the Minnesota Timberwolves or Phoenix Suns have to gain in making a deal that would help them more in the short term? Could anything even work with the contracts Philadelphia signed this offseason?

New Orleans could do a lot worse than acquiring top-15 point guard on a solid (and moveable) contract, a first round pick, two controllable, low-cost rotation pieces (who would fit well with Zion), and a couple fliers in Bender and the second rounders.

The Bucks would have to calculate what’s the bigger risk, rolling the dice with Playoff Bledsoe and standing pat (or exploring lesser moves) with the picks from the Brogdon deal? Or shaking up an incredibly talented roster with terrific chemistry when they’re already the best team in the NBA?

Jrue Holiday might not make a meaningful difference to the Bucks’ regular season win total. But I think he raises their postseason ceiling considerably, and would give Milwaukee a better chance to host a championship parade in June.

That would be a risk worth taking.