Does Bill Simmons' Trade Idea of Rudy Gay to the Milwaukee Bucks Make Sense?

Andy BaileyFeatured ColumnistOctober 18, 2013

TORONTO, CANADA - SEPTEMBER 30:  Rudy Gay #22 of the Toronto Raptors poses for a portrait during a Media Day on September 30, 2013 in Toronto, Canada. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this Photograph, user is consenting to the terms and condition of the Getty Images License Agreement. Mandatory Copyright Notice: 2013 NBAE (Photo by Ron Turenne/NBAE via Getty Images)
Ron Turenne/Getty Images

Bill Simmons gave us a two-for-one on trade ideas during the latest episode of he and Jalen Rose's 2013 NBA Preview. While discussing the Bucks, Simmons threw out the possibility of swapping the expiring contracts of Milwaukee's Caron Butler and Ekpe Udoh for Rudy Gay of the Toronto Raptors.

Here's the proposal from Simmons:

As you saw, he threw out the possibility of working basically the same deal with Chicago's Luol Deng instead of Gay. I've already explained why I think that one's no good.

For the purposes of this discussion, let's focus on the potential swap with the Raptors. 

The deal as constructed by Simmons works in ESPN's NBA Trade Machine, and makes sense to me for a couple reasons—but only if the Raptors are out of the hunt and looking to tank by the time the trade deadline rolls around.

If that's the case, new general manager Masai Ujiri may want to unload the team's most burdensome contract and start looking toward the future.


Why it Works for Toronto

May 9, 2013; Denver, CO, USA; Denver Nuggets general manager Masai Ujiri during the press conference naming him NBA executive of the year at the Pepsi Center. Mandatory Credit: Chris Humphreys-USA TODAY Sports
Chris Humphreys-USA TODAY Sports

Toronto pulling the trigger on this would essentially be about finances, and little else. Butler and Udoh will make $12.5 million this year and be free agents this summer. Gay is set to make $37.2 million over the next two seasons if he exercises the player option on the second year of the deal.

That's a huge savings for the Raptors, and gives them some more financial flexibility during the summer of 2014. Flexibility with which Ujiri could possibly work some of the magic he showed in Denver.

In terms of basketball, the deal may make the Raptors worse—but that's the point if you're tanking. And like I said, I don't think Toronto will entertain something like this unless they intentionally redirect their focus from the present to the future.

But if they wanted to defend this trade as a basketball move, they could. With Gay and DeMar DeRozan, the Raptors have two volume shooters on the wings. Even one volume shooter can be a problem for chemistry.

Butler may not be able to do many things at the same level as Gay these days, but he's still a better shooter (or at least he was last season). During 2012-13, Butler was better in both true shooting and effective field-goal percentages.

And DeRozan won't have to compete for shots with the 33-year-old Butler, whose been a role player since his days with the Dallas Mavericks.


Why it Works for Milwaukee

Oct 16, 2013; Toronto, Ontario, CAN; Toronto Raptors forward Rudy Gay (22) drives to the net against Boston Celtics forward Jeff Green (8) during the first half at Air Canada Centre. Mandatory Credit: John E. Sokolowski-USA TODAY Sports
John E. Sokolowski-USA TODAY Spo

If the Bucks are serious about staying out of the 2014 lottery (and it looks like they are), adding Rudy Gay could take them from being a fringe playoff team to a possible sixth or seventh seed in the Eastern Conference.

You might make the point that Gay would be as incompatible with Mayo as he is with DeRozan, but I'm not sure that's the case.

Mayo has become an increasingly unselfish player. His assist percentage has gone up significantly over the last two seasons, including a career-high mark of 19.4 in 2012-13.

He'd be setting Gay up for buckets a lot more often than he did when they played in Memphis together.

Butler would be a nice target for Mayo as well, and while he may have been a more efficient shooter last season, Gay holds better numbers in assist percentage, rebounding percentage and player efficiency rating. He even has a better defensive rating (an estimate of how many points a player gives up per 100 possessions).

As for losing Udoh, it shouldn't hurt Milwaukee much. They already have a wealth of young big men at center and power forward in Larry Sanders, Irsan Ilyasova, John Henson and Giannis Antetokounmpo.


Does it Make Sense?

I think this one does. Toronto unloads their biggest contract and frees itself up for the future, while Milwaukee upgrades at pretty much the only position where they're not set for the future (they have Brandon Knight, Mayo, Ilyasova and Sanders at the other spots).

A deal like this would be contingent upon each team's standing come February and if the Raptors aren't as good as they thought they'd be or the Bucks are competing for a playoff spot, it makes sense.


All stats courtesy of Basketball-Reference unless otherwise noted.

For 140-character pearls of wisdom from Bleacher Report's Andy Bailey, follow him on Twitter @AndrewDBailey.