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1999-2004 HIGH-PRICED VETERANS FAIL TO DELIVER

After their 1998 championship run, the Capitals finished the 1998–99 season with a record of 31-45-6 and failed to qualify for the playoffs. During the season, the team was sold to a group headed by AOL executive Ted Leonsis. The Capitals went on to win back-to-back Southeast Division titles in 2000 and 2001, yet both years lost in the first round of the playoffs to the Penguins. After the 2000–01 season, the team beat a midnight deadline and picked up the $3 million option on Adam Oates contract. Oates demanded a trade but management refused and stripped him of his team captaincy.

"I have no desire of coming back, and I'm not going to come back," Oates told The Washington Post. "I'm going to ask them to trade me. . . . The Caps will do just fine without me." Oates told the newspaper he felt he no longer was an important part of the team once the Capitals acquired centre Trevor Linden from Montreal in late March.

"After the trade, obviously the coach (Ron Wilson) lost faith in me. I was totally embarrassed by that, (getting benched) was the low point of my career," he said. Capitals general manager George McPhee declined to respond except to say, "He's a good hockey player and he has played well and we're going to exercise the option."

Meanwhile Leonsis, who already had one of the league best goaltenders in Olaf Kolzig, was looking to make a splash and add some serious star-power to his team in the hopes of a return to the Stanley Cup finals. What better way than to add someone who has hoisted the Cup in victory was his reasoning.

So, in the summer of 2001, the Capitals landed five-time Art Ross Trophy winner Jaromir Jagr by trading three young prospects to the Pittsburgh Penguins. Jagr was signed to the largest contract ever in NHL history — $77 million over seven years at an average salary of $11 million per year, with an option for an eighth year. However, after Adam Oates was traded to the Philadelphia Flyers, the Capitals failed to defend their division title and missed the playoffs in 2002 despite a winning record. Still, the addition of Jagr put more fans in the seats as the 2001–02 season marked the highest attendance in franchise history, drawing in 710,990 fans and 17,341 per game. Jagr did lead the Caps in scoring 

79 points with 48 assists; but a far drop from the 90-plus point level he achieved eight times with the Penguins. Before the 2002–03 season, the Caps made more roster changes, including the signing of highly regarded Robert Lang as a free agent, a linemate of Jagr's from Pittsburgh. Jagr and Lang finished 1-2 in team scoring (77 and 69 points respectively). Washington returned to the playoffs in 2003, but disappointed fans again by losing in six games to the Tampa Bay Lightning after starting off with a two-game lead in the best-of-seven first-round series. The series is well-remembered for the three-overtime Game 6 at the then–MCI Center. At the time it was the longest game in the building's history and was eventually decided by a power-play goal by Tampa Bay.

In the 2003–04 season, the league had a cloud of uncertainty hanging over it as the Collective Bargaining Agreement (CBA) between the NHL and the players was set to expire at the end of the season. With many teams operating in the red and the lack of a television contract comparable to the other three major league sports, the NHL was prepared to take a hard line in the upcoming negotiations. With this murkiness in play, the Capitals turned in one of their worst seasons since the expansion days. A 23-46-10 mark dropped the Caps into last place in the Southeast Division. Coach Bruce Cassidy was 25 games into the season with an 8–16–1 record when he was let go and replaced by assistant coach Glen Hanlon. Captain Steve Konowalchuk was dealt early in the season to Colorado and no replacement captain was named; another sign that Washington was operating as a rudderless ship. The Caps would go on and finish with the third-worst record in the league under Hanlon (23–46–10–3=59 points), but won the draft lottery; allowing them to choose Alexander Ovechkin with their first overall pick in the 2004 NHL Entry Draft.

The Caps decided to unload much of their high-priced talent — not just a cost-cutting spree, but also an acknowledgment that their attempt to build a contender with high-priced veteran talent had failed. Jagr had never lived up to expectations during his time with the Capitals, failing to finish among the League's top scorers or make the post-season All-Star Team. The Caps tried to trade Jagr, but as only one year was left on the existing NHL Collective Bargaining Agreement (CBA) before it expired, few teams were willing to risk $11 million on an underperforming player. In 2004, Jagr was finally sent to the New York Rangers in exchange for Anson Carter and an agreement that Washington would pay approximately $4 million per year of Jagr's salary, with Jagr himself agreeing to defer (with interest) $1 million per year for the remainder of his contract to allow the trade to go ahead. This was quickly followed by Peter Bondra departing for the Ottawa Senators. Not long after, Robert Lang was sent to the Detroit Red Wings, as well as Sergei Gonchar to the Boston Bruins

The anticipated labor strife came to be as the entire 2004-05 season was cancelled as the two sides could not reach an agreement to end the lockout. Capitals fans would have to wait another year to see the debut of their soon-to-be franchise icon.

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