The Seattle SuperSonics had a rich history of hits as well as misses in free agency. That trend continued when the team relocated and rebranded as the Oklahoma City Thunder.

After all, there’s really no such thing as a “sure thing” in free agency, and the franchise has had its fair share of disappointments over the years.

Here are OKC/Seattle's five worst signings in free agency of all time.

5. Patrick Patterson3-year, $16.4 million contract with Thunder (2017)

After showing vast improvements to his game while with the Toronto Raptors, Patterson seemed like the perfect fit for the Thunder in the summer of 2017. The team had just acquired superstar Paul George, and Patterson was expected to claim the starting power forward spot.

Patrick Patterson, Clippers
ClutchPoints

The 6-foot-8 stretch 4, however, had to take a back seat when Carmelo Anthony joined the Thunder and declared he wouldn't accept a reserve role. The worst was yet to come for Patterson, as he underwent arthroscopic surgery on his left knee and missed training camp.

Patterson never regained his pre-injury form, notching career-worst averages in his two seasons in Oklahoma City. He averaged just 3.8 points and 2.3 rebounds in 14.7 minutes per game on 36.4 percent shooting from the 3-point area.

Patterson and the Thunder eventually agreed to a buyout in 2019.

4. Calvin Booth: 6-year, $34 million offer sheet with Sonics (2001)

As you will see later down on this list, the Sonics had a track record of overpaying undeserving big men. Seattle thought it was a good idea to invest heavily in Booth, a 6-foot-11 center who didn’t show all that much promise in his early days with the Washington Wizards and Dallas Mavericks.

Booth’s signing proved to be a flop from the get-go, as injuries limited him to just 15 games in his first season in Seattle. He simply became an expensive backup center for the Sonics and never averaged more than 6.2 points during his three-year tenure with the franchise.

3. Andre Roberson3-year, $30 million extension with Thunder (2017)

The first thing that stands out with Roberson are his glaring offensive limitations for a player listed as a shooting guard. The fact that he can’t shoot 3-pointers (25.7 percent) or free throws (46.7) to save his life is indeed troublesome.

Andre Roberson, Thunder

However, he is a standout defensive irritant capable of locking down the best scorers in the league. The Thunder were willing to pay a premium for that trait alone and rewarded him with a lucrative deal after he made it on the All-Defensive Second Team in 2017.

Poised for an even bigger role the following year, Roberson got bit by the injury bug pretty hard. A ruptured left patellar tendon forced him to undergo season-ending surgery in 2018. He has experienced multiple setbacks during his rehab process and hasn’t returned to the court since. The 6-foot-7 swingman last played for the Thunder on January 27, 2018.

2. Jim McIlvain: 7-year, $33.6 million deal with Sonics (1996)

A lot of bigs got paid in the summer of ’96, including the likes of Shaquille O'Neal, Alonzo Mourning, and Juwan Howard.

The Sonics followed suit by offering a sizable deal of their own to a glorified backup center, Jim McIlvain. We won’t fault you if you don’t even know the guy.

McIlvaine didn’t even have an impressive resume in his stay with the Washington Bullets. Yet for some unknown reason, the Sonics decided to shell out the big bucks for him. In retrospect, he got paid more than Sonics starters Sam Perkins and Hersey Hawkins.

In fact, his salary was close to team stars Shawn Kemp (Kemp was not happy and was gone a year later) and Detlef Schrempf. His numbers, however, proved otherwise. The Sonics gave him the minutes and even started him for 151 games in two seasons. In return, he gave them putrid averages of 3.5 points, 3.7 rebounds, and 1.9 blocks.

1. Vin Baker: 7-year, $86 million extension with Sonics (1999)

Unlike Mcllvain, who was underserving from the beginning, Baker’s initial play earned him the gargantuan extension he received in ’99. The 6-foot-11 marvel was the centerpiece of the three-team deal between the Sonics, Milwaukee Bucks, and Cleveland Cavaliers that sent the disgruntled Shawn Kemp to Cleveland in ’97.

Vin Baker
Elsa Hasch/All Sport

Baker was indeed ahead of his time, boasting feathery moves in the post while also being capable of stretching the D with his shooting. He was a four-time All-Star and actually played to that level in his first year in Seattle.

Seeing him as their franchise star moving forward, the Sonics locked him up with a lucrative seven-year deal in ’99. His production dipped shortly after receiving the huge contract after he admitted to suffering from an ugly alcohol addiction.

Baker never regained his All-Star form. The Sonics gave up on him after four seasons and shipped him to Boston.