It's been a tough year for the Toronto Raptors front office who struck out on the centre market in this offseason and have see their team drop from NBA contenders to bottom dwellers over the court of this season. There hasn't been much to be happy about lately, but at the very least Sunday afternoon's Milwaukee Bucks news should give Masai Ujiri and Bobby Webster something to smile about.

Shortly after noon on Sunday, the Bucks announced that they'd inked their 30-year-old guard Jrue Holiday to a four-year, $134 million max contract extension that will pay him an average of $32 million over the next three seasons before he has a $37 million player option for 2024-25. It was a deal the Bucks had to make after giving up two first-round picks, two first-round pick swaps, and Eric Bledsoe to acquire Holiday this past offseason. While that's great news for Milwaukee, it certainly makes that Fred VanVleet contract the Raptors signed last offseason look like a steal.

There was little doubt the Raptors were going to get a deal done with VanVleet when he hit free agency last fall. By all accounts, he wanted to return to the team and Ujiri called him the organization's top offseason priority prior to his free agency. It wasn't so much a matter of if he would re-sign, just a matter of how much would it cost?

Eventually, the two parties agreed on a four-year, $85 million deal with an opt-out after the third season. Compared to Holiday's deal, that's $12.5 million less per season.

While saving some dough is always nice, at a certain point it just comes down to getting the best player. Well, let's take a look at how the two players compare.

Fred VanVleet vs. Jrue Holiday

Fred VanVleetJrue Holiday

Age

27

Turning 31

Points

19.8 points per game

17.0 points per game

FG%

39.3%

50.9%

3-point Shooting

37.1% (9 attempts)

39.0% (4.8 attempts)

Assists

6.1 assists per game

5.4 assists per game

Pick-and-roll offence

71.9th percentile

68th percentile

FiveThirtyEight RAPTOR

7.1 Wins Above Replacement

4.5 Wins Above Replacement

BBall-Index LEBRON

5.70 Wins Added

3.00 Wins Added

ESPN's Value Added

213.9

214.3

It's tough to make an entirely fair one-to-one comparison based on the way the two guards are used. VanVleet has had to take more shots and often tougher shots than Holiday this season because of Toronto's lack of offensive options. Both are elite guard defenders with Holiday the more versatile of the two based on his size and strength and VanVleet the savvier of the two in terms of getting his hands on balls for deflections and steals.

Picking the better of the two guards in a vacuum is an extremely tough proposition. It's only when you account for the almost four-year age difference and the $50 million discrepancy in their contracts that it becomes a lot easier to pick which one you'd rather have.

At the end of the day, all that matters is having the best players under contract for the longest and in that sense, the Bucks still hold a massive advantage over the Raptors with Giannis Antetokounmpo, Khris Middleton, and now Holiday all locked up for at least the next two seasons. But when it comes to value, the Raptors clearly have the edge here. Eventually, when it comes time to make a move down the road, Toronto is going to have a lot more flexibility to do so.

Further Reading

Malachi Flynn is showing shades of Fred VanVleet these days

Nick Nurse sees a very high 'ceiling' with Gary Trent Jr. and it's easy to see why

Nick Nurse laughs at tanking question, but Raptors' focus should be on the future