Long after his retirement from the game, the Chicago Bulls franchise is still (and will always be) considered as Michael Jordan’s team. His greatness has been well documented throughout the years, that people often disregard the talent that Chicago managed to surround him with through free agency.

Nowadays, the Bulls' front office hasn’t found much success with one notable exception. But back then, they managed to sign some unwanted players who somehow reinvented their careers under the Bulls banner.

Players with expiring contracts who managed to re-sign with the Bulls were also as important to the franchise. Those iconic runs might not have been made possible had they not managed to retain their services, so we will be including them on this list as well.

Here are five of Chicago’s best free-agent signings in history.

Carlos Boozer (2010)

Boozer is the only player on this list that wasn’t part of the Jordan era. The 6-foot-9 power forward enjoyed his best years with the Utah Jazz but was still quite serviceable during his four-year stint in Chi-Town.

The Bulls hit it big with Booz in the summer of 2010, coming to terms with a sign-and-trade agreement with the Jazz. The deal was for five years, $75 million.  The two-time All-Star gave the Bulls squad a dominant scoring forward they craved at the time.

Boozer was quite limited on the defensive side of the floor, but he still gave Chicago a double-double threat each night with averages of 15.6 points and 9.5 rebounds during his Bulls tenure.

Toni Kukoc (re-signed with Bulls in 1994)

Toni Kukoc is perhaps one of the Bulls’ greatest clutch performers aside from Jordan. Following a rather controversial rookie contract in 1993, the Bulls re-signed the Croatian to a  contract for $24.45 million over six years after he had opted out of his rookie contract. This made him the Bulls’ highest played player at the time, topping Jordan and a disgruntled Scottie Pippen.

The 6-foot-11 lefty gave the Bulls another dependable scorer during Jordan’s hiatus from basketball and was a big part of the dynasty upon His Airness' return. Although he could have undoubtedly started for any team in the league, Kukoc accepted a reserve role for the Bulls and was rewarded with the 1996 Sixth Man of the Year recognition. He was part of Chicago’s 1996-98 three-peat.

Ron Harper (1994)

In 1994, the Bulls signed Ron Harper to a contract for five years, $19.4 million. The veteran guard had played the previous five seasons with the Los Angeles Clippers and was being pursued by the New York Knicks as well.

Prior to joining the Bulls who were re-tooling in the aftermath of Jordan’s first retirement, Ron Harper was considered a go-to scorer for the Cleveland Cavaliers and Los Angeles Clippers.

In the presence of Jordan and Pippen's greatness, Harper willingly took a backseat and reinvented himself as a defensive-minded and perimeter-oriented role player. The 6-foot-6 guard formed a terrific starting backcourt alongside Jordan and was a vital part of the Bulls’ dynasty. He developed a strong relationship with then Bulls head coach Phil Jackson and even joined his Los Angeles Lakers championship team in 2000 and 2001.

DeMar DeRozan (2021)

In August 2021, the Bulls got their man for the first time in many years when they landed DeMar DeRozan in sign-and-trade deal with the San Antonio Spurs, who received back Thad Young and three draft picks. DeRozan signed for three years and $85 million.

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In the first two years of the deal, DeRozan has averaged 26.2 points per game and made the All-Star team both years. Plus, the Bulls got the added bonus of DeRozan's daughter being at their games. In his three seasons with the Spurs, DeRozan averaged 21.6 points per game and did not make an All-Star team.

After extending the contract of Nikola Vucevic for three years, $60 million, they will be looking to build around him, DeRozan and Zach LaVine. With the success of DeRozan's deal, the Bulls should feel confident about adding through free agency now that the NBA free-agency period has opened.

Scottie Pippen (re-signed with Bulls in 1991)

As great as Scottie Pippen is at both ends of the floor, fans still remember him as Jordan’s de facto No. 2. His relationship with the Bulls' brass hasn’t always been amicable, and he was vocal about feeling undervalued by the franchise on several occasions.

The Bulls re-signing Pippen to a contract worth $18 million in 1991 was indeed one of the franchise’s best decisions. It’s no secret that he could have starred elsewhere, evidenced when Pippen led the Bulls on every statistical category upon Jordan’s first retirement.

If they allowed Pippen to walk right after their first title, the Bulls might not have won five more in the coming years. Defenses would have surely locked in even tighter on Jordan, considering they would have no longer had to deal with Pippen’s scoring. Also, Jordan would have carried the defense all by his lonesome had Pippen not been by his side.