The Chicago Bears are really trying to win a Super Bowl in 2027, bolstering their defensive front with an all-world talent in Jeffery Simmons via a blockbuster trade with the Tennessee Titans.

Simmons is arguably the league's best defensive tackle, a game-changer who should give the Bears much more push on the defensive line to get after the quarterback and slow down the run.

The price is the underlying risk. Just how often do these big trades lead to Super Bowl victories? The Bears are sending two first-round picks and a fourth-round pick to the Titans to get this done, which is the cost of business to land a superstar like Simmons. How often does this actually work?

We've gone through and looked at some similar moves over the years to see if the teams who made these big swings actually got what they wanted out of it: a Lombardi.

We'll look at recent trades for defensive superstars that featured multiple first rounders (or a move of equivocal value). This helpful list from The Athletic charts a number of moves we didn't cover but are worth considering, too, as well as the ones we did.

2026: Browns DE Myles Garrett to the Rams

The Rams shocked the NFL this summer by sending a 2027 first rounder, a 2028 second rounder, a conditional 2029 third rounder and outside linebacker Jared Verse (who has first-round value) to the Cleveland Browns for Garrett, the best defensive end in the game. So far, that trade has not worked out for the Rams at all. Garrett has only played in one game so far this season and missed the rest with an injury.

The Rams are 3-4, a massive disappointment considering the sky-high expectations going into the season. It's too early to say if this trade is a miss for the Rams (after all, Garrett is still Garrett), but a Super Bowl feels like a tough ask this season. With some big Rams headed for free agency (Puka Nacua, Davante Adams, Byron Young, Kobie Turner) and an aging Matthew Stafford not a lock to keep up his elite pace in the future, Los Angeles may regret parting with so much draft capital and a younger player in Verse for Garrett if it can't rebound hard in the second half of the 2026 season or in 2027. Garrett's health will be a big sticking point to this deal, too, especially if he's not able to regain the totality of the sheer ferociousness of his Cleveland days.

2025: Jets CB Sauce Gardner to the Colts

The Colts made a massive swing for Gardner ahead of the 2025 NFL trade deadline, sending two first rounders in 2026 and 2027 and wide receiver A.D. Mitchell to the New York Jets for elite cornerback Sauce Gardner. The person who made that trade, general manager Chris Ballard, has since been fired. The Colts are headed toward a massive rebuild, one that Gardner might not even be a part of as Indianapolis searches for more draft capital.

One Daniel Jones injury derailed Indianapolis' season last year, showing the fragility of big trade deadline swings. Gardner's calf injury from 2025 has possibly hampered his effectiveness this season, too. Just compare his 2025 passer rating allowed when targeted (65.1) to his 2026 number (103.5). The Colts being a dumpster fire is probably dragging everyone down, but that's a striking drop-off for Gardner. He just missed the Minnesota Vikings game with a calf issue in the same leg, too, though in a different spot. Even if the player you get is really good (Gardner certainly has been in the past), you can't dictate the terms of your season after the trade is made. Especially if Gardner ends up getting dealt in the near future, this is the cautionary tale for all contending teams. Be careful what you give away when you push all the chips in on any given season. If things go sideways, you may regret your boldness.

2025: Jets DT Quinnen Williams to the Cowboys

The Cowboys trading Micah Parsons created a need for a star on the defensive line in Dallas. Jerry Jones got one in Williams, for whom he traded a 2026 second rounder, a 2027 first rounder and defensive tackle Mazi Smith. Williams has played well for Dallas, but he hasn't been the game-changing talent to get Dallas into Super Bowl contention. The team is 3-4 and still alive in the NFC East, but nobody is taking this Cowboys team seriously as an actual title contender. The Dallas defense has struggled quite a bit this season, even if Williams has done his job.

That's the trouble with trading so much for a defensive player. They can cause chaos and help you win games, but they can't throw the ball or call the plays. The team has to play well for the trade to make sense. Smith didn't work out for the Jets, but the Cowboys haven't really changed all that much in team quality with Williams on the roster. If Dallas misses the playoffs this season, it may wish that it still had that 2027 first rounder intact.

2025: Cowboys OLB Micah Parsons to the Packers

The Packers moved heaven and earth to add Parsons, one of the best pass-rushers of his generation, ahead of the 2025 season in a blockbuster deal with the Cowboys. Dallas added two first rounders (2026, 2027) and defensive tackle Kenny Clark in the move, which was a steep price to pay for Green Bay. Parsons played incredibly well for the Packers as expected, but he unfortunately tore his ACL last December. The Packers only went 9-7-1 last season and got beat at Soldier Field by the Packer-hated Chicago Bears in the postseason.

Parsons has yet to return to the field this season for Green Bay, too. While it's fair to argue that Green Bay needed a player like Parsons to keep pace with the NFC North arms race, Parsons' ACL tear has made this a tougher trade to evaluate. The team hasn't looked like a Super Bowl contender yet without him in the lineup, so we guess this trade is a bit of a draw right now. Once Parsons gets back on the field, perhaps Green Bay will feel a bit better about losing those two first rounders. If the team wins a Super Bowl during the duration of Parsons' contract, this will look like a much better deal in hindsight.

2020: Jets S Jamal Adams to the Seahawks

The Adams trade is the ultimate cautionary tale for adding premier defensive talent in a blockbuster deal. The Seahawks sent two first rounders, a third rounder and safety Bradley McDougald to the Jets for Adams and a fourth rounder (that ironically became Super Bowl-starting safety Coby Bryant). While his 2020 Seahawks debut went well (9.5 sacks, 83 tackles in 12 games), he started to take a step back in 2021 and then missed a bunch of games during the 2022 and 2023 seasons with injuries.

The deal did not give the Seahawks the game-changing impact they were looking for. On the contrary, it was one of the big missteps that ended the Pete Carroll/Russell Wilson era of Seahawks football. The Adams trade did not work out for Seattle as hoped. It was just a classic whiff. However, the Seahawks eventually rebounded and won the Super Bowl this past February with Bryant on the field.

2019: Jaguars CB Jalen Ramsey to the Rams

The Rams are riverboat gamblers when it comes to adding premiere talent, the team's blockbuster Ramsey trade one that actually paid off as hoped in large part. The team sent its 2020 and 2021 first rounders and a 2021 fourth rounder to Jacksonville to acquire Ramsey, the new superstar for the L.A. secondary. That trade alone did not win the Rams a Super Bowl; the team trading for Detroit Lions quarterback Matthew Stafford sealed the deal there.

However, the Rams won a Lombardi Trophy with Ramsey earning All-Pro honors in 2021. Ramsey played a pivotal role in helping that Rams title team get to the top of the mountain, so we'll say this was a worthy deal for Les Snead and company. Snead's bet that his future firsts would hold less value because of winning held up quite nicely.

2018: Raiders OLB Khalil Mack to the Bears

The Bears have been here before. The Bears traded for a defensive superstar in Khalil Mack back in 2018, sending two first rounders, a third rounder and a sixth rounder to the Las Vegas Raiders (then in Oakland) for Mack, a second rounder and a conditional fifth. Mack etched his legend in the Windy City after that trade was made during the four seasons he played there, but the team did not contend for a Super Bowl in that window. Mack's first season in Chicago saw the Bears go 12-4, but the team then fell into successive 8-8 campaigns in 2019 and 2020 and suffered a tough 6-11 campaign in 2021 where Mack only played seven games.

Mack never won a playoff game in Chicago in two tries; the team arguably could have used that draft capital for more long-term pieces. Mack left for the Los Angeles Chargers in 2022; the Bears went through three straight losing seasons after that before its resurgence under coach Ben Johnson and quarterback Caleb Williams. As much as Mack is revered by Bears fans, that trade did not work out for Chicago outside of the 2018 season. They'll have to hope the Simmons deal ages better. Otherwise, this could be another Mack situation in the making: great player, diminished results.