First term

In 1994, Carl Gutierrez teamed up with Senator Madeleine Bordallo, the widow of former Governor Ricardo Jerome Bordallo, to run for the island's highest office once more on a platform of "Helping the People of Guam." In the primary, they were challenged by the Democratic team of Edward D. Reyes and Gloria B. Nelson. The Gutierrez-Bordallo team received 9,555 votes while the Reyes-Nelson team received only 6,450 votes.^[12] In the 1994 General Election, the Democratic team of Gutierrez-Bordallo faced the Republican team of Thomas V.C. Tanaka and Doris Flores Brooks. During the general election, Tanaka-Brooks outspent the Gutierrez-Bordallo team by over $100,000, but Carl Gutierrez and Madeleine Bordallo won the election in a landslide with 23,405 votes, while Tanaka-Brooks had 19,281.^[12]

Upon assuming office on January 2, 1995, Governor Carl T.C. Gutierrez focused his work in the areas of infrastructure so that all the marginalized people will be brought into the 20th century before it went out and also pushing for economic development by aggressively completing 85% of his Vision 2001 plan by the end of 1999. Despite a super majority Republican Legislature that opposed virtually every executive initiative, the Gutierrez-Bordallo administration was successful in guiding the island through the rough waters of economic downturns throughout the region.

The tourism economy was also severely affected by the crash of Korean Airlines Flight 801 on August 6, 1997. During the rescue efforts, Gutierrez was one of the first responders and the first to reach the burning plane along with Dep. Fire Chief Chuck Sanchez and his security police officer Cecil Sulla. Gutierrez was credited with saving several lives, including 11-year-old Rika Matsuda ^[13] and Barry Small, an injured helicopter mechanic from New Zealand, who called Governor Gutierrez a "Hero." Gutierrez received the Eagle Award, the highest award given to a civilian by the U.S. National Guard Bureau. He was recognized by the governments of Japan and the Republic of Korea.

In December 1997, Typhoon Paka struck Guam. The strong winds from Paka left around 1,500 buildings destroyed on the island,^[14] of which 1,160 were single-family homes.^[15] A further 10,000 buildings sustained damage to some degree,^[14] with 60% of the homes on the island reporting major damage.^[15] In all, about 5,000 people were left homeless due to the typhoon. Additionally, an estimated 30–40% of the public buildings received major damage.^[15] Buildings on the island made of reinforced concerted fared well, as opposed to light metal-frame structures, which more often were completely destroyed. Large tourist hotels near Hagåtña, on which Guam is dependent, received generally minor damage, such as broken windows and damaged power generators.^[14]

A complete island-wide power outage followed the typhoon; damage to the main electrical transmission and distribution system was estimated at USD16 million. Following the passage of the typhoon, 25% of the homes on Guam were left without water.^[15] Telephone service remained working after the storm, due to most lines being underground. Strong waves washed away a few coastal roads in the northern portion of the island, leaving them temporarily closed. The waves surpassed the seawall at Apra Harbor, damaging the road and infrastructure of the seaport; many boats were washed ashore after breaking from their moorings. Strong winds damaged a radar system and lights along the runway of the Antonio B. Won Pat International Airport, though most airport facilities received light damage. The Andersen Air Force Base also sustained heavy damage, with hundreds of downed trees and many facilities left damaged.^[14] Across Guam, damage was estimated at USD500 million.^[15] About 100 people were injured,^[16] but the typhoon caused no deaths on the island.^[15]

Second term

In 1998, Governor Carl Gutierrez ran for reelection with Lieutenant Governor Madeleine Z. Bordallo. There were two Democratic teams that challenged the Gutierrez-Bordallo team in the primary. Senator Thomas C. Ada and Senator Lou Leon Guerrero ran as a team, as did Senator Angel L.G. Santos and Jose T. "Pedo" Terlaje. The Gutierrez-Bordallo carried the 1998 Democratic primary with 16,838 votes, compared with only 9,788 for Ada-Leon Guerrero and 6,295 for Santos-Terlaje.^[17] In the 1998 General Election, Gutierrez-Bordallo faced the Republican team of Former Governor Joseph Franklin Ada and Senator Felix Perez Camacho. The election resulted in a second term for Governor Carl T.C. Gutierrez and Lieutenant Governor Madeleine Z. Bordallo, who won with 24,250 votes, compared with 21,200 votes for Ada-Camacho.^[17] In the 1998 Gubernatorial election against former governor Joe Ada, an election challenge by Ada/Camacho went all the way to the U.S. Supreme Court. The decision by the Supreme court was 9–0 in favor of Gutierrez/Bordallo, thus ending the Republican challenge.

Just following the reelection of Governor Carl T.C. Gutierrez and Madeleine Z. Bordallo, President William Jefferson Clinton visited Guam on November 23, 1998.^[18] The visit was the first since 1986 when a sitting U.S. president had visited Guam. Thousands of Guamanians gathered on the field in front of the Ricardo J. Bordallo Governor's Complex to see President Clinton. The crowd was treated to a rousing rendition of the Star Spangled Banner by Joseph "Uncle Tote" Cunningham and several speakers addressed the assembled crowd.^[19] President Clinton was introduced by youth speaker Michael F.Q. San Nicolas.^[20]

Gutierrez's credibility and integrity have been under constant attack by those who oppose him and his style of leadership. Beginning when he was still in office, efforts are continuing to try to find him guilty of purported crimes. He has never been found guilty of any crime, winning all cases that went to trial. Other cases were thrown out of court because they had no merit.

His second term in office was marked by political instability caused by the 1998 election challenges, a supermajority Republican (12–3) Guam Legislature, an unsuccessful Recall Movement in 2000 after the Supreme court decision came out giving Gutierrez/Bordallo the win, the "rolling" power outages left behind by the Ada/Blas administration, the destruction of the island's infrastructure by Supertyphoons Chata'an, Paka, and Pongsona.