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NBA Trades: 3 packages to help the Milwaukee Bucks move George Hill

Dalton Sell
Dalton Sell

Behind the Bucks Pass

MILWAUKEE, WISCONSIN - DECEMBER 22 (Photo by John Fisher/Getty Images)

Milwaukee Bucks: Jrue Holiday, Grayson Allen, Portland Trail Blazers: Justise Winslow
MILWAUKEE, WISCONSIN – FEBRUARY 14 (Photo by Patrick McDermott/Getty Images)

After a rather successful 2022 NBA Draft, the Milwaukee Bucks will now attempt to retool their roster further through trades and free agency.

Among the most prominent priorities for general manager Jon Horst should be finding an upgrade at the backup point guard position. George Hill just had an incredibly lackluster campaign, having a season to forget as he put up some of the worst numbers in his career. Considering that the guard just turned 36-years-old, Hill’s best years in the league are almost certainly behind him, so moving his $4 million salary for the 2022-23 season should be explored as the Bucks look to improve their bench brigade. With all that being said, here are three trade packages to help the Milwaukee Bucks move George Hill this offseason.

A George Hill trade between the Milwaukee Bucks and Portland Trail Blazers

This trade between the Milwaukee Bucks and Portland Trail Blazers is far from anything seismic. Milwaukee would land a former first round pick in Justise Winslow while sending a veteran guard in George Hill to the Blazers, who appear to be collecting pieces to contend next season. It is not a glamorous deal, but it could make sense for both parties involved.

For the Bucks, Winslow could be an interesting piece to add to this roster. Though the former Duke product has bounced around the league over the past few years, perhaps joining a contender such as the Bucks could help Winslow find his footing. The 26-year-old has managed to stay in the NBA due to his pestering defense and relentless hustle, which the Bucks are always looking to stock up on. Standing at 6-foot-6, Winslow could also help shore up another huge problem of Milwaukee’s, which is their versatility. Winslow can play and defend several positions at a high level, and it was clear in the 2022 playoffs that the Bucks need more players that can do that. When they were up against bigger wings like Jayson Tatum and Jaylen Brown, the Bucks had no answer to combat the pair defensively, and someone like Winslow could provide some help in that regard.

Getting Hill off the books would also allow the Bucks to offer soon-to-be free agent Jevon Carter a legitimate role next season. As Carter ponders his option in free agency, the chance to stick around in Milwaukee and play an actual role next season with Hill gone could be enticing after he was left on the bench throughout most of the 2022 postseason.

From Portland’s point of view, adding Hill would give them a veteran ball-handler off the bench to run the point when Damian Lillard is catching his breath. The Blazers could use some added depth at the point guard position, given that aside from Lillard, they do not have too much personnel at the position. Former Buck Eric Bledsoe is on their roster, but the franchise will have until July 10 to decide whether or not to fully guarantee his $19.4 million salary for next season. Considering that the alternative is waiving Bledsoe and paying just $3.9 million, they will likely look to let the guard go and seek a different backup. Hill is not the flashiest name, but he could fit the billing.

Financially, trading these two players straight up works, as Winslow is set to make just a tick more than Hill will next season. Considering that this trade would allow the Bucks to move Hill, bring in a versatile forward, and potentially open to door to bring Carter back to town, they should ponder it.

Milwaukee Bucks: Jrue Holiday, OKC Thunder: Kenrich Williams
MILWAUKEE, WISCONSIN – NOVEMBER 19 (Photo by John Fisher/Getty Images)

A George Hill trade between the Milwaukee Bucks and OKC Thunder

This would be another player for player swap, but the Milwaukee Bucks would have to add some second round picks as a sweetener here. Kenrich Williams of the OKC Thunder has been linked to opposing teams in the rumor mill for months now, and it is certainly no secret that the front office is always looking to add more draft picks whenever they can. The Bucks should attempt to trade for the 27-year-old forward, as bringing him in could help address some of their current issues.

First, it has been said time and time again that the Bucks need to add a small ball power forward this offseason. This team is oftentimes at their most lethal when they go small and utilize lineups with Giannis Antetokounmpo at center, but they were not as impactful this past season due to the absence of a small ball four. Williams could provide some assistance in that regard, as he stands at 6-foot-6 and can play either forward position. Although Williams is not an outstanding long-range shooter like the Bucks would prefer, having knocked down 34.6 percent of his career 3-pointers on 2.5 attempts, he would still be a solid option for them to fill their small ball forward vacancy.

For OKC, they have not been shy about taking on veterans in the past when opposing teams are willing to attach some form of draft capital. General manager Sam Presti would likely do the same here by adding a pair of second rounders to their war chest of assets. As for Hill, this may actually be a decent opportunity for him, as the Thunder would likely approach him with a potential buyout on impact, given their surplus of guards already in tow. That would allow Hill to pick his next team in free agency, giving him some options to consider. If not, perhaps the Thunder could look to flip him for more assets in a trade if teams came calling about a backup point guard, just like they did when OKC shipped Hill to the Philadelphia 76ers in 2021. Of course, that is all speculation, but it is how the Thunder have operated in the past.

The financial aspect of this deal would actually benefit the Milwaukee Bucks, as Williams is set to make $2 million less than Hill next season. That should make this trade only more enticing for the Bucks, even if they have to include a pair of second rounders to get it done. Once again, this would allow the Bucks to offer Jevon Carter a more prominent role as he braces for free agency, so doing this deal would be killing multiple birds with one stone.

Milwaukee Bucks: Pat Connaughton, New York Knicks: Derrick Rose
MILWAUKEE, WISCONSIN – NOVEMBER 05 (Photo by John Fisher/Getty Images)

A George Hill trade between the Milwaukee Bucks and New York Knicks

Year in and year out, the Milwaukee Bucks and Derrick Rose get linked to one another in the rumor mill. If the Bucks are finally looking to bring Rose to Milwaukee this offseason, they could consider this proposed trade with the New York Knicks to get it done.

On impact, Rose would be an upgrade over Hill. While he is not the MVP player that he once was, Rose has found new life over the past several seasons in a backup role, as the guard has averaged 16.2 points and 4.6 assists per game over the last four years. Numbers like that could patch up the Bucks’ lack of bench production that plagued them throughout last season, giving them a reliable ball-handler behind Jrue Holiday that could contribute at a high level. There are concerns with the veteran’s health, as he has dealt with injuries throughout his career, which included being limited to just 26 games last season, but if the Bucks want to go all-in with finding a new backup, Rose could be their best bet.

While losing Hill would be reasonable, including Allen would be a tougher pill to swallow. It would have to happen for salary matching purposes, but some fans could be hesitant to include him in a package like this after the guard just had the best season of his career. However, on the other end of the spectrum, Allen did just have an abysmal playoff run where he was virtually unplayable vs. the Boston Celtics in round two, so those concerns could linger. Ultimately, it depends on just how badly the Bucks want to upgrade at the backup point guard position and whether or not they feel as if Rose would be worth parting ways with Allen to acquire.

Although Rose is a favorite for New York’s head coach Tom Thibodeau, the Knicks would likely entertain this deal, as they have shown recently that they are doing whatever it takes to clear cap space. Making trades to move Kemba Walker, Alec Burks, and Nerlens Noel recently, the Knicks are cleaning house to try and sign Jalen Brunson once free agency begins, and Rose could be the next player on the move. This particular package would not only help the Knicks save $2 million, but it would also give them a veteran point guard in Hill and a marksman in Allen, which could make it all the more enticing.

Stay tuned to see what the Milwaukee Bucks end up doing with George Hill this offseason.

Dalton Sell

Dalton Sell

Dalton Sell is the site expert of Behind the Buck Pass. He's covered the NBA, primarily the Milwaukee Bucks, since 2019. Covering Milwaukee's turbulent 2021 title run and seeing the franchise snap its 50-year championship drought during his first full season as a site expert serves as the highlight of his writing career to date. When he's not focused on the day-to-day headlines involving the Milwaukee Bucks, he enjoys watching classic horror films and hitting the gym.