Lamar Jackson’s mega deal certainly puts him even further under the microscope.

While perhaps the most prominent re-signing in Baltimore sports history, it is far from the first. For this issue, we take a look back at some of those players who have re-upped in Baltimore throughout the years. Many of these deals panned out quite well. Others were among the worst contracts in professional sports history.

We limited the scope of this list to the modern era of pro sports (1990 and beyond) simply because of how dramatically money has changed.

So here are “The 15 Prominent Baltimore Sports Re-Signings.” Players are listed in alphabetical order. Both Jackson and Roquan Smith were left off the list because we do not have evidence yet by which to judge the deals.

1. Brady Anderson: Five years, $31 million (1997)

Anderson had re-upped with a three-year, $10.25 million pact in 1994 that included an option for 1997. So that particular contract was the one that covered the best stretch of the outfielder’s career, including his, umm, “historic” 50-homer season in 1996. But there was real fear that Anderson might leave after ‘97, with serious interest from teams like the Braves and (gulp) Yankees. The good news is that the Orioles got the deal done. The bad news is that Anderson had just one very productive season (1999) during the length of the deal and deteriorated to the point that he was simply released after the fourth season.

2. Chris Davis: Seven years, $161 million (2016)

Me: “The Brady Anderson contract was bad.”

The literal next entry on the list: “Hold my beer.”

I’m not sure what else there is to say. The Davis signing seemed, at the time, to be an encouraging sign that the Orioles were serious about extending their window after disappointing free-agent departures the previous offseason. Instead, the former slugger slowly regressed into one of the worst hitters in baseball before ultimately working out a deal with the team to “retire” in 2021.

3. Joe Flacco: Six years, $120.6 million (2013)

We move from the worst re-signing in Baltimore sports history to the most polarizing. After Flacco’s historic 11-touchdown, zero-interception playoff run to the Super Bowl XLVII title, the Ravens had little choice but to make their quarterback (briefly) the highest-paid player in NFL history. They did, however, have other choices, which for some reason never seemed to include prioritizing wide receivers. Flacco had an outstanding 2014 season working with offensive coordinator Gary Kubiak, but there was almost nothing else to show for this deal.

4. J.J. Hardy: Three years, $40 million (2014)

Just a day before the start of the American League Championship Series, the Orioles kept the good times rolling by announcing that one of their pending free agents would be sticking around. It was the second three-year extension Hardy had signed with the club, with the first coming in 2011.

The results? Mixed. Hardy continued to be a steady presence at shortstop but never reached double-digit home runs again (after clubbing 77 from 2011-2013) and hit below .220 in two of the three seasons. Making matters worse, the free agents who departed were Nelson Cruz, Nick Markakis and Andrew Miller, all of whom reached at least one All-Star Game in their next destination.

5. Adam Jones: Six years, $85.5 million (2012)

Finally, something positive to reflect on. Jones’ new deal was one of the most impactful moments in modern Orioles history, a surprising announcement that appeared to capitalize on the Orioles’ stunning hot start to the season. The beloved center fielder reached four straight All-Star Games and helped lead the Orioles to three playoff appearances, but his value as an ambassador of the team and city may have been even greater. This was truly one of the greatest contracts in Baltimore sports history.

6. Ray Lewis: Seven years, $44.5 million (2009)

It’s easy to forget how likely Lewis’ departure appeared as free agency opened in 2009. Former Ravens defensive coordinator Rex Ryan chose to have the Jets sign fellow unrestricted free-agent Baltimore linebacker Bart Scott instead, paving the way for the future Hall of Famer to return to Charm City. Scott gave an emotional boost to the Gang Green defense but never made another Pro Bowl. Lewis had two more All-Pro seasons and three more Pro Bowl appearances in him and gave an emotional lift to the Super Bowl XLVII title team.

7. Nick Markakis: Six years, $66.1 million (2009)

In the midst of the Orioles’ “dark ages,” this offered some hope. Markakis was a talented young outfielder coming off back-to-back .300 seasons and the Orioles decided to get ahead of his arbitration years. He became a central part of the team’s turnaround, hitting .270 or better in all six seasons of the deal. Unfortunately, the Orioles declined their half of a mutual option for 2015 and allowed Markakis to depart because of health concerns. He had six more good seasons in Atlanta.

8. Chris McAlister: Seven years, $55 million (2004)

After being hit with back-to-back franchise tags, the reigning first-team All-Pro cornerback reached a long-term deal with the Ravens early in the 2004 season. The results were mixed. He was an All-Pro again in ‘04 and tallied a career-high six interceptions (and two touchdown returns) in 2006. But he largely fell off the cliff after that, including an extremely awkward exit in 2008 during John Harbaugh’s first season.

9. Mike Mussina: Three years, $21 million (1997)

Orioles fans of a certain age know all about Mussina departing the Orioles for the Yankees. But we can’t overlook the story of Mussina taking what was considered a “hometown discount” to avoid free agency a few years earlier. At the height of the steroid era (and with the Orioles declining as a team), Mussina maintained a sub-3.80 ERA in all three seasons before ultimately departing.

10. Haloti Ngata: Five years, $61 million (2011)

The Ravens have almost always used the franchise tag as a method to extend a negotiating window and keep a player around (only Wally Williams and Matt Judon did not ultimately sign). Ngata received the tag, signed early in the season then reached three straight Pro Bowls and helped the Ravens to the Super Bowl XLVII title during the span of the deal.

11. Ray Rice: Five years, $40 million (2012)

Rice established himself as one of the more unique offensive weapons in football during the first four years of his career, making it an easy decision for the Ravens to sign him long term after giving him the franchise tag. Rice played a key role during the 2012 championship season but had a disappointing 2013 campaign and then was released in the aftermath of a 2014 domestic violence incident.

12. Cal Ripken Jr.: Five years, $32.5 million (1992)

It was the richest deal in baseball history at the time, coming on the heels of his second MVP season the year before. Not only did Ripken continue to perform at a high level during the life of this contract, it was the deal that made sure he’d break Lou Gehrig’s consecutive games played record in an Orioles uniform.

13. Brian Roberts: Four years, $40 million (2009)

On the heels of Markakis’ extension, this was another pleasant surprise as the Orioles smartly locked down the two-time All-Star second baseman (and doubles machine). The deal actually kicked in starting in 2010 and, unfortunately, did not prove fruitful. Injuries derailed his career, and Roberts played a total of just 192 games across the four seasons.

14. Terrell Suggs: Six years, $62.5 million (2009)

Like others on this list, Suggs was signed just before the deadline to avoid playing under the franchise tag. Oddly, the contract got off to a rough start as Suggs posted a very-unlike-himself 4.5 sacks in ‘09. But after that, he finished with double-digit sacks in every full season he played, was part of the Super Bowl XLVII title team and earned another four-year deal from the Ravens after 2014.

15. Justin Tucker: Four years, $16.8 million (2016)

Perhaps you’ve forgotten that after he was given the franchise tag by the team, negotiations were going so poorly that ESPN reported Tucker planned to leave Baltimore if he didn’t get a deal before the tag deadline. Thankfully, we’ll never have to wonder if he was bluffing. Tucker was an All-Pro in every year of the deal before signing another four-year contract and continuing on his path toward the Hall of Fame.

Issue 282: August/September 2023

Photo Credits: Kenya Allen and Sabina Moran/PressBox

Originally published Aug. 16, 2023

Glenn Clark

See all posts by Glenn Clark. Follow Glenn Clark on Twitter at @glennclarkradio