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In August 2018, incidents involving a break-in and threats to Til Schweiger, a neighbour in Mallorca, and an alleged attack on an escort in a Frankfurt hotel, led to his admission to a psychiatric hospital. On 28 August 2019, he was required by court to pay €7,200 in damages to the assaulted escort.

In 2017, he was convicted in Switzerland of drunk driving, in relation to a 2014 car crash in which two people were injured, and received a suspended sentence of four years plus a fine of €10,000. Issues with alcohol and drugs led to his separation from his wife Sara at the end of 2017.

In June 2013, Ulrich went on record stating that he'd "always said that Lance wouldn't get out of it. He made too many enemies." Later that month, he admitted that he doped with the help of Spanish doctor Eufemiano Fuentes. His name was on the list of doping tests published by the French Senate on 24 July 2013 that were collected during the 1998 Tour de France and found positive for EPO when retested in 2004.

On 17 January 2013, the day Armstrong admitted to doping in his seven Tour wins, he was stripped of his 3rd-place finish at the 2000 Sydney Olympics men's time trial race. On 13 September 2013, Armstrong said that he had sent back the bronze medal to the International Olympic Committee. On 2 October, the IOC confirmed that it had received the medal.

In 2006, Ullrich was barred from the Tour de France amid speculation of having doped. In February 2012, Ullrich was found guilty of a doping offence by the Court of Arbitration for Sport. He was retroactively banned from 22 August 2011, and all results gained since May 2005 were removed from his Palmarès. He admitted to blood doping in 2013.

In February 2012, Ullrich was found guilty of a doping offence by the CAS. He was retroactively banned from 22 August 2011, and all results gained since May 2005 were removed from his Palmares. Ullrich published a statement on his website, that said he would not appeal the decision. He admitted that he had had contact with Fuentes, which he considered a mistake that he now regrets.

In 2010, with the doping allegations still ongoing, Ullrich was diagnosed with burn-out, and avoided public appearances for a few months. When Lance Armstrong announced his comeback as a professional cyclist, Ullrich made clear that he was not going to do the same.

In 2008, the German investigation was closed after a settlement, which by German law means Ullrich was found not guilty. The Swiss investigation was still ongoing at that time, but they closed the case in February 2010, because Ullrich was no longer member of the Swiss Cycling Federation, and so they had no jurisdiction after he retired. The UCI appealed that decision at the Court of Arbitration for Sport (CAS).

On Monday, 26 February 2007, Ullrich retired. At the press conference in Hamburg he said, "Today, I'm ending my career as a professional cyclist. I never once cheated as a cyclist." He said he would be an advisor to Team Volksbank.

During the 2006 Giro d'Italia, Ullrich was mentioned in a doping scandal, Operación Puerto. Ullrich denied the rumors. However, on 30 June 2006, one day before the Tour de France, he was suspended from participating. Ivan Basso and other riders were also excluded. On 20 July 2006, Ullrich was fired from T-Mobile. General manager Olaf Ludwig announced the news during the 18th stage of the Tour between Morzine and Macon. Ullrich said his dismissal was 'unacceptable.'

On 3 August 2006, doping expert Werner Franke claimed Ullrich purchased about €35,000 worth of doping products a year based on documents uncovered in the Operación Puerto doping case. A German court imposed a gag order on Franke after it found there was not enough evidence to link Ullrich to doping. On 14 September 2006, officials raided Ullrich's house and collected DNA material while Ullrich was honeymooning with his new wife Sara. On 4 April 2007, Ullrich's DNA sample, had "without a doubt" matched nine bags of blood taken from Eufemiano Fuentes' office.

On 18 October 2006, Ullrich laid off his personal physiotherapist Birgit Krohme. Speculation rose that this was a sign that Ullrich had given up hope of returning to racing. Ullrich denied these rumors. One day later, Ullrich canceled his licence of the Swiss Cycling Federation, and was looking for a different federation for a licence of 2007. Ullrich claimed that the Swiss Cycling Federation had to stop their doping investigation, but the Swiss federation continued the investigation. On 25 October 2006, a document from the Spanish court on Ullrich's website stated that no charges would be filed.

In May 2006 Ullrich launched Jan Ullrich Collection bicycles, which he helped to develop.

For 2005, Ullrich again captained T-Mobile. He maintained a low profile for the early season, surfacing in the 2005 Tour de Suisse, which he finished third behind Aitor González and Michael Rogers.

The day before the 2005 Tour de France, Ullrich was training when his team car stopped unexpectedly. Ullrich hit the back window, ending up in the back seat of the car. Less than 24 hours later Ullrich was passed by Armstrong in the time trial. Ullrich fell again in the mountains, bruising his ribs. He could not keep up with Armstrong or Ivan Basso. Ullrich began focusing on finishing ahead of Michael Rasmussen for a podium position. He rode a good second time trial, beating all but Armstrong. Rasmussen had several crashes and bike changes, which gave Ullrich a podium place in the Tour.

Armstrong retired after the Tour in 2005. Ullrich decided to ride one or two more years. Early reports said Ullrich was in better shape than previous years and could be ready for his second victory in the Tour. Ullrich finished 115th in the Tour de Romandie on 30 April. However, he injured his knee in the off-season, which could have limited his performance in the 2006 Tour, had he participated (see below).

For 2004 Ullrich returned to Team Telekom, now named T-Mobile. He won the Tour de Suisse. In the Tour de France, he finished fourth, 8:50 behind Armstrong, his first finish lower than second. Klöden finished second and Ivan Basso third.

On 13 January 2003, Ullrich, along with his advisor Rudy Pevenage, joined Team Coast on a multi-million Euro deal. Financial problems at the team were known from the beginning of the season. These led to the Coast team folding in May 2003. Ullrich moved on to the newly-founded Team Bianchi, set up from the remainders of Coast by Jacques Hanegraaf, a former cyclist at Team Telekom.

The 2003 Tour de France was the first for many years that Ullrich had not been considered a favorite. In the first week, Ullrich became sick and almost retired. He lost a minute and a half on Armstrong in the Alps. Ullrich fought back in the time trial. Armstrong had trouble with the heat and lost one and a half minutes to Ullrich. Ullrich was within a minute of Armstrong in the classification. The next day, he closed the gap by another 19 seconds in the first mountain stage. Two days later Ullrich rode away from Armstrong on the Tourmalet but Armstrong caught up. Half way into the next climb, Luz Ardiden, Armstrong's handlebar got caught in a spectator's yellow musette waving in the air and he fell. Ullrich waited for Armstrong to recover, returning the courteous display by Armstrong 2 years previously. Armstrong then caught the group and attacked shortly afterwards.

Ullrich lived in Merdingen, Germany, from 1994 to 2002 with his partner Gaby Weiss, with whom he had a daughter, Sarah Maria, on 1 July 2003. They moved to Scherzingen, municipality of Münsterlingen, Switzerland, in 2002. Since separating in 2005, said to be because Weiss's reluctance to be in the limelight conflicted with Ullrich's celebrity life, Ullrich has continued to live in Scherzingen. Weiss returned with Sarah to Merdingen. In September 2006 Ullrich married Sara Steinhauser, sister of his former teammate and training partner, Tobias Steinhauser. Their first child, Max, was born five weeks prematurely on 7 August 2007. Their second son, Benno, was born on 25 January 2011. Their third son, Toni, was born on 31 October 2012.

In May 2002, Ullrich had his driver's license revoked after a drunk driving incident. After a positive blood sample for amphetamine in June 2002, Ullrich's contract with Team Telekom was ended, and he was banned for six months. He said he had taken ecstasy with amphetamine. He had not been racing since January due to a knee injury, and the German Cycling Federation's disciplinary committee agreed that he was not attempting to use the drug for performance enhancement, so he was given a minimum suspension.

Following a disappointing 2002 season, Ullrich was looking for a new team, with interest coming from CSC–Tiscali, Saeco Macchine per Caffè–Longoni Sport, and Phonak.

The 2000 Tour de France brought Ullrich, Marco Pantani and Armstrong against each other for the first time. Armstrong proved too strong and won then and again in 2001. Ullrich crashed in 2001 and Armstrong waited for him to return to his bike. Ullrich cited his failure to defeat Armstrong as why he fell into depression next year.

Ullrich rode well in the 2000 Summer Olympics in Sydney, Australia. After establishing a three-man break with Telekom teammates Andreas Klöden and Alexander Vinokourov, Ullrich won the gold with Vinokourov second and Klöden rounding out the all-Telekom podium. He won the silver in the time-trial, losing by only seven seconds to Viatcheslav Ekimov but beating Armstrong soundly into third.

The IOC has investigated if Ullrich should be stripped of his gold medal won at the 2000 Olympic Games, which was possible because there was an eight-year deadline for investigations, and the investigation started after seven years. It was decided that there was no solid evidence against Ullrich, and that Ullrich could keep his medal.

In the following year during the inaugural Deutschland Tour, Ullrich fell after getting entangled with Udo Bölts during stage 3. He had a knee injury and could not ride the 1999 Tour, which ended in the first of seven 'victories' for Lance Armstrong. Ullrich set his targets on the world time trial championship in October by riding the Vuelta.

Ullrich was defending champion in 1998. He took the lead in the general classification on stage 7, a time trial, over 58 km of undulating roads. However, on stage 15 Marco Pantani blew the Tour apart with a victory which began on the Galibier. Ullrich was without support when Pantani attacked. Pantani topped the Galibier alone. It was misty and the roads were wet. The descent was dangerous and Pantani increased his lead. By the bottom of the final climb, Les Deux Alpes, Pantani had nearly four minutes. Telekom brought Udo Bölts and then Riis to pace Ullrich. Pantani was race leader as he crossed the line. Ullrich finished almost nine minutes back, dropping to fourth position, six minutes behind Pantani.

The Tour of 1998 was haunted by doping affairs, giving it the nickname "Tour de Dopage."

Ullrich had 2 wins before the 1997 Tour; a stage in the Tour de Suisse and the national Road Race championship a week before the tour. He became favorite in the 1997 Tour de France. He started strongly, finishing second in the prologue behind Chris Boardman. On stage 9, the first mountain stage which was won by Laurent Brochard, Ullrich worked for Riis. Only on the last ascent when Richard Virenque attacked did Ullrich react. Riis struggled to keep up and finished 30 seconds behind Virenque, Marco Pantani and Ullrich. On stage 10 from Luchon to Andorra Arcalis, with Riis again falling back, Ullrich dropped back to the team car to ask permission to attack. He returned to the lead group and pushed up the climb leaving Pantani and Virenque. He finished a minute ahead which earned his first yellow jersey as leader of the general classification. L'Équipe, greeted Ullrich with Voilà le Patron ("Here is the boss"). Ullrich won the Stage 12 time trial with three minutes between himself and the second placed rider, Virenque, who had started three minutes in front of him.

Ullrich gave up a place in the 1996 German Olympic team to ride his first Tour. He finished the prologue 33 seconds down. He stayed within the top 20 until the mountains on stage 7 when Miguel Indurain cracked. Ullrich finished 30 seconds back, 22 behind his teammate Bjarne Riis while Indurain finished four minutes down. On the following stage, he finished in the same group as Indurain 40 seconds behind Riis. On stage 9, Riis rode into the yellow jersey as leader of the general classification while Ullrich finished 44 seconds back and also into 5th place overall 1-minute 38 seconds from Riis.

In 1995, Ullrich turned professional for the Telekom team under Walter Godefroot.

Ullrich was inconspicuous in his first 18 months as a professional. In 1995 he became national time trial champion. He also achieved top ten placings on stages of the 1995 Tour de Suisse. At 21 he wanted to start the 1995 Tour de France but Godefroot thought it was early. Instead he went to the small German stage race, the Hofbräu Cup, where he ended third. Ullrich started the 1995 Vuelta a España later that year only to abandon on stage 12.

In 1993, aged 19, Ullrich won the amateur road title at the UCI Road World Championships in Oslo, as Lance Armstrong won the professional championship. The following year, he finished third behind Chris Boardman and Andrea Chiurato in the world time trial championship in Sicily.

At a young age, Ullrich joined the club, SG Dynamo Rostock (de) in his hometown. He won his first bicycle race at the age of nine while riding in sports shoes and on a rented bicycle. He was educated in the sports training system of the German Democratic Republic attending the KJS sports school in Berlin in 1986. In 1988, he was champion of the German Democratic Republic. The school closed two years after the fall of the Berlin wall in 1989. He, his trainer Peter Sager, and teammates joined an amateur club in Hamburg until 1994. In 1991, he was 5th in the amateur cyclo-cross world championships.

Jan Ullrich (German pronunciation: [ˈjan ˈʊlrɪç] ); born 2 December 1973) is a German former professional road bicycle racer. Ullrich won gold and silver medals in the 2000 Summer Olympics in Sydney. He won the 1999 Vuelta a España and the HEW Cyclassics in front of a home crowd in Hamburg in 1997. He had podium finishes in the hilly classic Clásica de San Sebastián. His victorious ride in the 1997 Tour de France led to a bicycle boom in Germany. He retired in February 2007.

Marco Pantani attacked on the stage to the Alpe d'Huez. Ullrich, who was nine minutes ahead of Pantani overall, limited his losses to 47 seconds. Pantani attacked again on the Morzine stage and won, while Ullrich again limited his losses. In the final time trial, won by Abraham Olano, Ullrich extended his lead over Virenque and the following day became the first German to win the Tour de France. At 23, Ullrich was the fourth youngest winner of the Tour since 1947. Two weeks later, he won the Hews Cycling Classic in Hamburg. A further two weeks later Ullrich was beaten by Davide Rebellin in a sprint in the GP Suisse. He was chosen "sports person of the year" in Germany in 1997.