Should Raptors trade for Tyler Herro in Damian Lillard deal? The case for and against pursuing the Heat guard

It’s no secret that Damian Lillard wants to be traded to the Heat, but there’s a holdup.

Since the Heat can only offer two first-round picks, they would likely have to part with Tyler Herro to acquire Lillard. The problem? Trail Blazers don’t want Herro, according to ESPN’s Adrian Wojnarowski.

Wojnarowski adds that there are teams that would “give up a good first-round pick to the Blazers — maybe something more” to land Herro in a three-team trade with Miami and Portland. Should the Raptors be one of those teams?

TSN’s Scott Rafferty and Jordan Greer argue for and against a Herro trade.

MORE: What Dennis Schroder brings to Raptors as Fred VanVleet replacement

The case

Should the Raptors trade for Tyler Herro?

The arguments

Scott Rafferty says yes: Herro is a polarizing player, but he fills a need for the Raptors.

Over the past two seasons, Herro has averaged 20.4 points per game. He was named Sixth Man of the Year in 2021–22 and was promoted to a full-time starter in 2022–23. While he has his flaws, he has proven to be a capable scorer and high-volume 3-point shooter from the guard position, both as a starter and reserve.

The Raptors were a miserable 3-point shooting team last season, ranking 28th out of 30 teams in do and percentage. Herro is a threat from the catch and from the dribble. That combination would ease his fit next to Pascal Siakam and Scottie Barnes and help fill some of the void left by Fred VanVleet.

Tyler Hero vs. Fred VanVleet 3-point shooting (2022-23 season)
Tyler Hero Fred VanVleet
Catch-and-shoot 105-274 (38.3%) 104-297 (35.0%)
Pull up 96-260 (36.9%) 103-307 (33.6%)

The concern with Herro is his contract — he signed a four-year, $120 million extension last year that starts in 2023-24 and ends in 2026-27. That’s a lot of money to take on for a shoot-first guard not known for his passing or defense, but if the price is basically salary and a first-round pick, I think it’s worth a shot.

Plus, Herro, 23, is on a similar timeline to Barnes, and I don’t think his addition would hinder the development of Gradey Dick. Not only is Dick more of a traditional shooter, but he has the size 6-8 to be a guard or forward. Having him and Herro on the field would be a huge boost to Toronto’s spacing.

Jordan Greer says no: I agree with Scott’s point about Herro filling a need for the Raptors. As the numbers show, he would certainly provide shooting for a team that can struggle from the perimeter.

The question here is what adding Herro means to the bigger picture in Toronto.

Let’s say the Raptors acquire Herro and hope to stay competitive. That means they will likely keep Siakam and OG Anunoby, both of whom will expect significant salaries. Toronto would spend a lot of money on Anunoby, Herro and Siakam over the next four years.

Oh, by the way, Jakob Poeltl just got $80 million over four years. And don’t forget Barnes’ extension in the not-so-distant future. Will the Raptors lock into that core of players? Realistically, how far will that group go?

And while Herro is a proven offensive creator in the regular season, he hasn’t exactly lit up the scoreboard in the playoffs.

Outside of the Heat’s 2020 “bubble” run, Herro has averaged 11.9 points on 39.9 percent shooting from the field and 25.8 percent from deep in 20 playoff games. Miami was three wins away from a title this year with an injured Herro watching from the sidelines.

As for the rebuilding path, yes, Herro is on Barnes’ timeline, but wouldn’t Toronto rather select its own young prospect in the draft or save its assets for a better deal than chase someone who isn’t an All-Star? As Wojnarowski reported, we’re talking at least a “good first-round pick,” but the price is likely higher.

The verdict

Gilbert McGregor (@GilMcGregor_): This is actually closer than I first thought it would be, but I’ll say it no, the Raptors shouldn’t trade for Tyler Herro.

In the end, it comes down to cost — having to part with a future first-round pick for Herro is a big price to pay since Toronto doesn’t own its 2024 pick because of the Poeltl trade. On top of that, you’re parting with a first-round pick to take on Herro’s big salary, which, as outlined by Jordan, is tacked on to potential paydays for players whose deals are about to expire.

The last thing Toronto wants to do is become a team that has no control over its own pick for X years to come. If Herro was a perennial All-Star, it would be eligible. The risk is not worth what Toronto would gain by entering into the deal. The big picture is crucial

Kyle Irving (@KyleIrv_): Both Scott and Jordan made valid arguments for and against, but I say yes, the Raptors should trade for Tyler Herro.

Toronto has lacked shot creators and perimeter shooters over the past few seasons. The personnel void has played a big role in its ranking at the bottom of the league at the bottom of the league for the past two years, per cleaning the glass. Herro would give the Raptors an immediate solution in that aspect, and he fits perfectly on the timeline of younger cornerstones on the roster like Scottie Barnes and Gradey Dick.

And why are we so sure he won’t be an All-Star caliber player? Herro is only 23 years old with plenty of room to grow his game.

The salaries — especially with future extensions for Pascal Siakam, OG Anunoby and Barnes — are where it gets tricky, but the reality is that Toronto may move on from one of the previous two players before those salaries even arrive.

If the opportunity is there, call, Masai.

Carlan Gay (@TheCarlanGay): I want to say yes, the Raptors should trade for Tyler Herro as well.

The guys above talked about the lack of shooter and playmaking and how Herro could potentially solve that, so I won’t go over that.

The most important thing here is the money, right? I know it’s a lot of money, with extensions for Siakam, OG and Barnes looming, but Herro is worth the risk. You would acquire a 23-year-old who turns up in the Nordics with a chip on his shoulder. Like Kyle, I like Herro’s chances to be an All-Star one day in the right situation.

The draft pick would be hard to lose, but it’s not like Toronto needs more young prospects after acquiring Herro. The Raptors also won’t be pulling in the lottery if everything falls right for them — that would likely be a pick that’s more in their teens or early 20s.

It would be great to have a young player ready to step up under team control for the next four years. The Raptors haven’t exactly knocked it out of the park with free agents in team history, and players don’t often see Toronto as a destination when looking to escape their current situation. Herro is talented and would be a great addition at the right time and age.

Final result: Yes (2), No (1)

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